ZIDOVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13N5O4
Molecular Weight	267.2413
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O

InChI

InChIKey=HBOMLICNUCNMMY-XLPZGREQSA-N

InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H13N5O4
Molecular Weight	267.2413
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00495
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. Zidovudine, a structural analog of thymidine, is a prodrug that must be phosphorylated to its active 5′-triphosphate metabolite, zidovudine triphosphate (ZDV-TP). It inhibits the activity of HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleotide analogue. It competes with the natural substrate dGTP and incorporates itself into viral DNA. It is also a weak inhibitor of cellular DNA polymerase α and γ. Zidovudine is used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections. Zidovudine is marketed as Retrovir.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
DU-145 2 Target ID: CHEMBL613508 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12893431	Inhibitor 8297	24.0 µM [IC50]
MCF7 21 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12893431	Inhibitor 8297	22.0 µM [IC50]
Human immunodeficiency virus type 1 reverse transcriptase 67 Target ID: CHEMBL247 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/24794751 \| https://www.ncbi.nlm.nih.gov/pubmed/9001825	Inhibitor 8297	0.01 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	Primary		Approved 8429	RETROVIR Approved Use RETROVIR is a nucleoside analogue reverse transcriptase inhibitor indicated for: -- Treatment of Human Immunodeficiency Virus (HIV-1) infection in combination with other antiretroviral agents. (1.1) -- Prevention of maternal-fetal HIV-1 transmission. (1.2) Launch Date 1987

C_max

Value	Dose	Analyte	Population
1.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019910s041lbl.pdf	2.5 mg/kg 6 times / day steady-state, intravenous dose: 2.5 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	ZIDOVUDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg 6 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.55 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg 6 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg 6 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg 6 times / day steady-state, intravenous dose: 150 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.16 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.74 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.72 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1400 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019910s041lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.32 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg 6 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.65 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg 6 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.28 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg 6 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.31 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg 6 times / day steady-state, intravenous dose: 150 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.26 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.39 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	60 mg single, intravenous dose: 60 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.74 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.22 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.33 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019910s041lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg 6 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg 6 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg 6 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg 6 times / day steady-state, intravenous dose: 150 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	60 mg single, intravenous dose: 60 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1803995	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	ZIDOVUDINE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
62% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019910s041lbl.pdf	2.5 mg/kg 6 times / day steady-state, intravenous dose: 2.5 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:		ZIDOVUDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20000 mg single, oral Overdose Dose: 20000 mg Route: oral Route: single Dose: 20000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3163102/	unhealthy, 28 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 28 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3163102/	Disc. AE: Anemia... AEs leading to discontinuation/dose reduction: Anemia (grade 1, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3163102/
1000 mg 1 times / day steady, oral Highest studied dose Dose: 1000 mg, 1 times / day Route: oral Route: steady Dose: 1000 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1, homosexual Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	Other AEs: Depression... Other AEs: Depression (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/
22.5 g single, oral Overdose Dose: 22.5 g Route: oral Route: single Dose: 22.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1, homosexual Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	Disc. AE: Dizziness, Diarrhoea... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Diarrhoea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/
20000 mg single, oral Overdose Dose: 20000 mg Route: oral Route: single Dose: 20000 mg Co-administed with:: temazepam Sources: https://pubmed.ncbi.nlm.nih.gov/2900428/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2900428/	Disc. AE: Drowsiness... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2900428/
36 g single, oral Overdose Dose: 36 g Route: oral Route: single Dose: 36 g Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	unhealthy, 35 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 35 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	Disc. AE: Seizure... AEs leading to discontinuation/dose reduction: Seizure (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/
134 mg single, oral Overdose Dose: 134 mg Route: oral Route: single Dose: 134 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21867364/	healthy, 4 day n = 1 Health Status: healthy Condition: HIV postnatal prophylaxis Age Group: 4 day Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/21867364/	Disc. AE: Metabolic acidosis exacerbated... AEs leading to discontinuation/dose reduction: Metabolic acidosis exacerbated (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/21867364/
8000 mg/m2 multiple, intravenous MTD Dose: 8000 mg/m2 Route: intravenous Route: multiple Dose: 8000 mg/m2 Co-administed with:: 5-fluorouracil(500 mg/m2) Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/	unhealthy, adult n = 29 Health Status: unhealthy Condition: metastatic colorectal cancer Age Group: adult Sex: unknown Population Size: 29 Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/	Disc. AE: Cardiac arrhythmia... Other AEs: Diarrhea... AEs leading to discontinuation/dose reduction: Cardiac arrhythmia (grade 5, 1 patient) Other AEs: Diarrhea (grade 3-4, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/
40 g single, oral Overdose Dose: 40 g Route: oral Route: single Dose: 40 g Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	unhealthy, adult n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	Disc. AE: Nystagmus... AEs leading to discontinuation/dose reduction: Nystagmus (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	Other AEs: Asthenia, Headache... Other AEs: Asthenia (9%) Headache (63%) Malaise (53%) Anorexia (20%) Constipation (6%) Nausea (51%) Vomiting (17%) Anemia (1%) Granulocytopenia (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	Other AEs: Fever, Hepatomegaly... Other AEs: Fever (25%) Hepatomegaly (11%) Nausea and vomiting (8%) Diarrhea (8%) Stomatitis (6%) Splenomegaly (5%) Cough (15%) Breath sounds abnormal (7%) Ear disorders NEC (7%) Congestion nasal (8%) Skin rash (12%) Lymphadenopathy (9%) Neutropenia (8%) Thrombocytopenia (1%) ALT (grade 3, 1%) Lipase (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037 inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT 35 P-gp 1461 BCRP 699 OAT3 642 MRP2 383 MRP3 157 MRP4 204 CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 OAT1 599 OAT2 145 OAT4 146 OCT1 512 OCT2 647 OCTN2 66 OATP1B1 788 OATP1B3 706 OATP2B1 123 MRP1 106	UGT 192 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A9 380 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213 CYP2A6 543 CYP2C8 693 CYP2C19 991 P-gp 1537 MRP4 77 MRP5 40 BCRP 561 OAT1 326 OAT2 115 OAT3 339 OAT4 78 OCT2 355

Drug as perpetrator

Target	Modality	Activity
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28712845/, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 <400 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28712845/	no [IC50 <500 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI5In19	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI5In19	no [IC50 >10 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP1 172	inhibitor 3277 Sources: https://journals.lww.com/aidsonline/Fulltext/2002/09060/The_protease_inhibitor_ritonavir_inhibits_the.5.aspx, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMDA0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no
OATP2B1 126	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/jm300212s	no
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OCTN2 71	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10525100/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjkzIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30928510/, https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	weak [IC50 31.34 uM]
UGT 59	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/1907149/	yes [Ki 1200 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OAT2 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTU1NzExIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/, https://pubmed.ncbi.nlm.nih.gov/19628728/	major [Km 770 uM]	yes (pharmacogenomic study) Comment: Km (Pooled HLMs) = 1.4 mM; The carriers of UGT2B7*1c had 57% lower mean AUC (P = 0.029, unpaired t-test), 196% higher mean CL/F (P = 0.004, unpaired t-test) (Figure 3B), and 67% shorter mean elimination half-life (P = 0.030, unpaired t-test) compared with non-carriers. Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/, https://pubmed.ncbi.nlm.nih.gov/19628728/
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	minor
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	minor
OCT2 355	substrate 3367 Sources: https://jasn.asnjournals.org/content/13/7/1703, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
OAT3 339	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes [Km 145.1 uM]
OAT4 78	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes [Km 151.8 uM]
UGT 192	substrate 3367 Sources: https://www.info.pmda.go.jp/go/interview/2/166272_6250001M1038_2_RVC_1F.pdf#page=23, https://pubmed.ncbi.nlm.nih.gov/1907149/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=030516871 Page: (PMDA drug information) 23	yes [Km 2400 uM]
OAT2 115	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTU1NzExIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes [Km 26.8 uM]
OAT1 326	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes [Km 45.9 uM]
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18464048/, https://pubmed.ncbi.nlm.nih.gov/15345326/	yes
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18535159/	yes
MRP5 40	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18535159/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19472342/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI5In19

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:10110	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10110
MolPort	MolPort-002-507-286	https://www.molport.com/shop/molecule-link/MolPort-002-507-286
Selleck Chemicals	zidovudine-retrovir	http://www.selleckchem.com/products/zidovudine-retrovir.html
ZINC	ZINC000003779042	http://zinc15.docking.org/substances/ZINC000003779042
eMolecules	479032	https://www.emolecules.com/cgi-bin/more?vid=479032
eMolecules	747869	https://www.emolecules.com/cgi-bin/more?vid=747869

PubMed

Title	Date	PubMed
Synthesis of 4'-substituted nucleosides and their biological evaluation.	1999	10780412
Synthesis and anti-HIV activity of unusual nucleoside oxanosine derivatives.	1999	10780358
Synthesis and antiviral activity of 1-[1,5-dialkyl-1H-1,2,4-triazol-3-yl)methyl]thymines.	1999 Apr	10327888
Antiviral activity and resistance profile of phosphazid--a novel prodrug of AZT.	1999 Apr-May	10432707
Long-term effects of prenatal 3'-azido-3'-deoxythymidine (AZT) exposure on intermale aggressive behaviour of mice.	1999 Aug	10494581
Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides.	1999 Aug	10480262
A new point mutation (P157S) in the reverse transcriptase of human immunodeficiency virus type 1 confers low-level resistance to (-)-beta-2',3'-dideoxy-3'-thiacytidine.	1999 Aug	10428942
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide.	1999 Aug	10428899
Charge modification of plasma and milk proteins results in antiviral active compounds.	1999 Dec	10628656
N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1.	1999 Dec 20	10617082
Zidovudine (AZT) induced alterations in mitochondrial biogenesis in rat striated muscles.	1999 Jan	10535663
Synthesis of dual function (5R,6R)- and (5S,6S)-5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(para-bromophenyl methoxyalaninyl phosphate) as novel spermicidal and anti-HIV agents.	1999 Jan	10079878
PMTI, a broadly active unusual single-stranded polyribonucleotide, inhibits human immunodeficiency virus replication by multiple mechanisms.	1999 Jan	10079876
Characterization of human immunodeficiency virus type 1 resistant to modified cyclodextrin sulphate (mCDS71) in vitro.	1999 Jan	10079875
Substituted 7H-pyrido[4,3-c]carbazoles with potent anti-HIV activity.	1999 Jan 18	10021911
Biological evaluation of proanthocyanidin dimers and related polyphenols.	1999 Jul	10425115
Zidovudine-induced experimental myopathy: dual mechanism of mitochondrial damage.	1999 Jul 1	10475107
Correlation of anti-HIV activity with structure: use of electrostatic potential and conformational analysis.	1999 Jul 19	10450963
A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody.	1999 Jun	10403680
Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus.	1999 Jun 7	10386942
Inhibition of human immunodeficiency virus replication by RD6-Y664, a novel benzylhydroxylamine derivative.	1999 Mar	10335401
Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217.	1999 Nov	10628806
Resistance of the human immunodeficiency virus to the inhibitory action of negatively charged albumins on virus binding to CD4.	1999 Nov 20	10580404
Synthesis and anti-retroviral activity of O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) phosphoramidate derivatives.	1999 Oct	10616733
Synthesis of 2',3'-dideoxy-2'-fluoro-L-threo-pentofuranosyl nucleosides as potential antiviral agents.	1999 Oct	10616728
Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.	1999 Oct	10508010
Pyrrolobenzoxazepinone derivatives as non-nucleoside HIV-1 RT inhibitors: further structure-activity relationship studies and identification of more potent broad-spectrum HIV-1 RT inhibitors with antiviral activity.	1999 Oct 21	10543890
Persistent mitochondrial dysfunction and perinatal exposure to antiretroviral nucleoside analogues.	1999 Sep 25	10509500
Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.	2000 Jan	10602742
Antioxidant function of phenethyl-5-bromo-pyridyl thiourea compounds with potent anti-HIV activity.	2000 Jan 3	10636251
3-year suppression of HIV viremia with indinavir, zidovudine, and lamivudine.	2000 Jul 4	10877738
Spiropentane mimics of nucleosides: analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity.	2000 Mar 10	10814087

Patents

Sample Use Guides

In Vivo Use Guide

Treatment of HIV-1 infection: Adults: 600 mg/day in divided doses with other antiretroviral agents. Pediatric patients (6 weeks to <18 years of age): Dosage should be calculated based on body weight not to exceed adult dose.

Route of Administration: Oral

In Vitro Use Guide

The antiviral activity of CD8(+) cells from 2 LTSs was inhibited by 5 uM of zidovudine.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:17:05 GMT 2023` Edited by `admin` on `Sat Dec 16 16:17:05 GMT 2023`
Record UNII	4B9XT59T7S
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ZIDOVUDINE

Official Name

English

ZIDOVUDINE [EP MONOGRAPH]

Common Name

English

BW-A509U

Code

English

AZIDOTHYMIDINE

Systematic Name

English

3'-DEOXY-3'-AZIDOTHYMIDINE

Systematic Name

English

THYMIDINE, 3'-AZIDO-3'-DEOXY-

Systematic Name

English

ZDV

Common Name

English

ZIDOVUDINE [MI]

Common Name

English

COMBIVIR COMPONENT ZIDOVUDINE

Common Name

English

ZIDOVUDINE [USP-RS]

Common Name

English

ZIDOVUDINE [EP IMPURITY]

Common Name

English

AZT

Common Name

English

ZIDOVUDINE COMPONENT OF TRIZIVIR

Brand Name

English

TRIZIVIR COMPONENT ZIDOVUDINE

Brand Name

English

ZIDOVUDINE [IARC]

Common Name

English

ZIDOVUDINE COMPONENT OF LAMIVUDINE/ZIDOVUDINE TEVA

Brand Name

English

ZIDOVUDINE COMPONENT OF COMBIVIR

Common Name

English

ZIDOVUDINE [USAN]

Common Name

English

ZIDOVUDINE [JAN]

Common Name

English

COMPOUND S

Code

English

ZIDOVUDINE [EMA EPAR]

Common Name

English

ZIDOVUDINE [ORANGE BOOK]

Common Name

English

ZIDOVUDINE [VANDF]

Common Name

English

RETROVIR

Brand Name

English

3'-AZIDO-3'-DEOXYTHYMIDINE

Systematic Name

English

ZIDOVUDINE [MART.]

Common Name

English

ZIDOVUDINE [USP MONOGRAPH]

Common Name

English

3'-AZT

Common Name

English

ZIDOVUDINE [WHO-IP]

Common Name

English

3'-AZIDOTHYMIDINE

Systematic Name

English

ZIDOVUDINE [HSDB]

Common Name

English

zidovudine [INN]

Common Name

English

BW-A-509U

Code

English

NSC-602670

Code

English

Zidovudine [WHO-DD]

Common Name

English

ZIDOVUDINUM [WHO-IP LATIN]

Common Name

English

LAMIVUDINE/ZIDOVUDINE TEVA COMPONENT ZIDOVUDINE

Brand Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

COMBIVIR (AUTHORIZED: HIV INFECTIONS)

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

FDA ORPHAN DRUG

8185

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

WHO-VATC

QJ05AR04

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

WHO-ATC

J05AR05

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

WHO-ATC

J05AF01

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

NDF-RT

N0000175462

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

WHO-VATC

QJ05AR01

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

WHO-ATC

J05AR04

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

NCI_THESAURUS

C1557

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

NDF-RT

N0000175459

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

NCI_THESAURUS

C97452

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

NDF-RT

N0000009947

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

NDF-RT

N0000175459

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

EMA ASSESSMENT REPORTS

LAMIVUDINE/ZIDOVUDINE TEVA (AUTHORIZED: HIV INFECTIONS)

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

WHO-ESSENTIAL MEDICINES LIST

6.4.2.1

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

WHO-ATC

J05AR01

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

WHO-VATC

QJ05AR05

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

WHO-VATC

QJ05AF01

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

LIVERTOX

NBK548210

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

NDF-RT

N0000175459

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

Code System Code Type Description

WHO INTERNATIONAL PHARMACOPEIA

ZIDOVUDINE

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

PRIMARY

Description: A white or brownish powder. Solubility: Soluble in ethanol (~750 g/l) TS, sparingly soluble in water. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Zidovudine should be kept in a tightly closed container, protected from light. Additional information: Zidovudine may exhibit polymorphism. Definition: Zidovudine contains not less than 97.0% and not more than 103.0% of C10H13N5O4, calculated with reference to the dried substance.

USAN

Y-51

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

PRIMARY

NCI_THESAURUS

C947

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

PRIMARY

DRUG CENTRAL

2861

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

PRIMARY

CAS

30516-87-1

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

PRIMARY

MESH

D015215

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

PRIMARY

LACTMED

Zidovudine

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

PRIMARY

RS_ITEM_NUM

1724500

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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IUPHAR

4825

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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FDA UNII

4B9XT59T7S

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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SMS_ID

100000088002

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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RXCUI

11413

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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RxNorm

DRUG BANK

DB00495

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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EPA CompTox

DTXSID8020127

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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EVMPD

SUB00153MIG

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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MERCK INDEX

m11592

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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Merck Index

DAILYMED

4B9XT59T7S

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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WIKIPEDIA

ZIDOVUDINE

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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ChEMBL

CHEMBL129

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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NSC

602670

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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PUBCHEM

35370

Created by admin on Sat Dec 16 16:17:09 GMT 2023 , Edited by admin on Sat Dec 16 16:17:09 GMT 2023

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HSDB

6515

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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INN

6118

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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CHEBI

10110

Created by admin on Sat Dec 16 16:17:08 GMT 2023 , Edited by admin on Sat Dec 16 16:17:08 GMT 2023

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Related Record Type Details


					5840721PJZ

OAT-2

TRANSPORTER -> SUBSTRATE

Amount:


					8O1GL13IL5

ZIDOVUDINE SODIUM

SALT/SOLVATE -> PARENT

Amount:


					4B9XT59T7S

ZIDOVUDINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

USP

Amount:


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					4B9XT59T7S

ZIDOVUDINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

EP

Amount:


					4AF605U6JN

MRP-2

TRANSPORTER -> NON-SUBSTRATE

Amount:


					I81U7H57XI

OAT-1

TRANSPORTER -> SUBSTRATE


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> SUBSTRATE


					0M77ZW789J

URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7

METABOLIC ENZYME -> SUBSTRATE

Amount:


					QQ3V9BPL5D

ABCC5

TRANSPORTER -> NON-SUBSTRATE

Amount:


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> SUBSTRATE

Amount:


					A3Z87NSO0U

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE

TARGET -> INHIBITOR

Amount:

Related Record Type Details


					K7ZG448V5M

ZIDOVUDINE DIPHOSPHATE

METABOLITE ACTIVE -> PARENT

Amount:


					97YMU05VPJ

ZIDOVUDINE MONOPHOSPHATE

METABOLITE ACTIVE -> PARENT

Comments:

AMOUNT FORMED FOLLOWING ADMINISTRATION

Interaction Type:

MINOR

Amount:


					6RGF96R053

ZIDOVUDINE TRIPHOSPHATE

METABOLITE ACTIVE -> PARENT

Amount:


					7W21M0C25B

3'-AMINO-3'-DEOXYTHYMIDINE

METABOLITE TOXIC -> PARENT

Amount:


					CD09F5JM6T

ZIDOVUDINE GLUCURONIDE

METABOLITE INACTIVE -> PARENT

Amount:


					CD09F5JM6T

ZIDOVUDINE GLUCURONIDE

METABOLITE INACTIVE -> PARENT

Comments:

AMOUNT OF EXCRETED

Interaction Type:

MAJOR

Amount:

Related Record Type Details


					QR26YLT7LT

THYMINE

IMPURITY -> PARENT

Comments:

The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity C (thymine) about 0.3. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1): - the area of any peak corresponding to impurity C, when multiplied by a correction factor of 0.6, is not greater than four times the area of the principal peak in the chromatogram obtained with solution (2) (2.0%).

Amount:


					WF6985DLTU

3'-(3-(3-AZIDO-2,3-DIDEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-3,6-DIHYDRO-5-METHYL-2,6-DIOXO-1(2H)-PYRIMIDINYL)-3'-DEOXYTHYMIDINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					VC2W18DGKR

DOXRIBTIMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					U97Q0OU9KB

TRIPHENYLCARBINOL

IMPURITY -> PARENT

Amount:


					8GQZ0LXH0C

3'-CHLORO-3'-DEOXYTHYMIDINE

IMPURITY -> PARENT

Comments:

The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity B about 1.2. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1):- the area of any peak corresponding to impurity B, is not greater than twice the area of the principal peak in the chromatogram obtained with solution (2) (1.0%).

Amount:


					BO9LE4QFZF

STAVUDINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (TLC)

Amount:


					QR26YLT7LT

THYMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Amount:


					8GQZ0LXH0C

3'-CHLORO-3'-DEOXYTHYMIDINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Amount:


					8GQZ0LXH0C

3'-CHLORO-3'-DEOXYTHYMIDINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Amount:


					QR26YLT7LT

THYMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Amount:


					IUO13CXB2Q

METHYL TRITYL ETHER

IMPURITY -> PARENT

Amount:


					BO9LE4QFZF

STAVUDINE

IMPURITY -> PARENT

Comments:

The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity A (stavudine) about 0.4;. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1):- the area of any peak corresponding to impurity A, when multiplied by a correction factor of 0.9, is not greater than the area of the principal peak in the chromatogram obtained with solution (2) (0.5%).

Amount:


					8NWA1GEX70

1-(2'-DEOXY-.BETA.-D-THREO-PENTOFURANOSYL)THYMINE

IMPURITY -> PARENT

Amount:


					U97Q0OU9KB

TRIPHENYLCARBINOL

IMPURITY -> PARENT

Comments:

Not Specified

Amount:


					PG7VYL4TJ6

3'-AZIDO-3'-DEOXY-5'-O-TRITYLTHYMIDINE

IMPURITY -> PARENT

Amount:

Related Record Type Details


					4B9XT59T7S

ZIDOVUDINE

ACTIVE MOIETY

Amount:

Name	Property Type	Parameters
Biological Half-life	PHARMACOKINETIC	Population PHARMACOKINETIC

CSF/PLASMA RATIO	PHARMACOKINETIC	Population PHARMACOKINETIC

Tmax	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC	Population PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC	Populations PHARMACOKINETIC

CSF/PLASMA RATIO	PHARMACOKINETIC	Population PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC

Route of Elimination	PHARMACOKINETIC

Route of Elimination	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC	Population PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC	Polpulation PHARMACOKINETIC

AE	Significance	Dose	Population
Anemia	grade 1, 1 patient Disc. AE	20000 mg single, oral Overdose Dose: 20000 mg Route: oral Route: single Dose: 20000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3163102/	unhealthy, 28 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 28 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3163102/
Depression	1 patient	1000 mg 1 times / day steady, oral Highest studied dose Dose: 1000 mg, 1 times / day Route: oral Route: steady Dose: 1000 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1, homosexual Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/
Diarrhoea	1 patient Disc. AE	22.5 g single, oral Overdose Dose: 22.5 g Route: oral Route: single Dose: 22.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1, homosexual Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/
Dizziness	1 patient Disc. AE	22.5 g single, oral Overdose Dose: 22.5 g Route: oral Route: single Dose: 22.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1, homosexual Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2036464/
Drowsiness	1 patient Disc. AE	20000 mg single, oral Overdose Dose: 20000 mg Route: oral Route: single Dose: 20000 mg Co-administed with:: temazepam Sources: https://pubmed.ncbi.nlm.nih.gov/2900428/	unhealthy, 34 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 34 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2900428/
Seizure	1 patient Disc. AE	36 g single, oral Overdose Dose: 36 g Route: oral Route: single Dose: 36 g Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	unhealthy, 35 years n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: 35 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/
Metabolic acidosis exacerbated	1 patient Disc. AE	134 mg single, oral Overdose Dose: 134 mg Route: oral Route: single Dose: 134 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21867364/	healthy, 4 day n = 1 Health Status: healthy Condition: HIV postnatal prophylaxis Age Group: 4 day Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/21867364/
Diarrhea	grade 3-4, 17%	8000 mg/m2 multiple, intravenous MTD Dose: 8000 mg/m2 Route: intravenous Route: multiple Dose: 8000 mg/m2 Co-administed with:: 5-fluorouracil(500 mg/m2) Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/	unhealthy, adult n = 29 Health Status: unhealthy Condition: metastatic colorectal cancer Age Group: adult Sex: unknown Population Size: 29 Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/
Cardiac arrhythmia	grade 5, 1 patient Disc. AE	8000 mg/m2 multiple, intravenous MTD Dose: 8000 mg/m2 Route: intravenous Route: multiple Dose: 8000 mg/m2 Co-administed with:: 5-fluorouracil(500 mg/m2) Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/	unhealthy, adult n = 29 Health Status: unhealthy Condition: metastatic colorectal cancer Age Group: adult Sex: unknown Population Size: 29 Sources: https://pubmed.ncbi.nlm.nih.gov/9261522/
Nystagmus	1 patient Disc. AE	40 g single, oral Overdose Dose: 40 g Route: oral Route: single Dose: 40 g Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/	unhealthy, adult n = 1 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2563536/
Anemia	1%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Vomiting	17%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Granulocytopenia	2%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Anorexia	20%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Nausea	51%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Malaise	53%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Constipation	6%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Headache	63%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Asthenia	9%	500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, adult n = 453 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 453 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Thrombocytopenia	1%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Hepatomegaly	11%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Skin rash	12%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Cough	15%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Fever	25%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Lipase	3%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Splenomegaly	5%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Stomatitis	6%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Breath sounds abnormal	7%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Ear disorders NEC	7%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Congestion nasal	8%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Diarrhea	8%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Nausea and vomiting	8%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Neutropenia	8%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
Lymphadenopathy	9%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf
ALT	grade 3, 1%	160 mg/m2 3 times / day steady, oral Recommended Dose: 160 mg/m2, 3 times / day Route: oral Route: steady Dose: 160 mg/m2, 3 times / day Co-administed with:: EPIVIR(4 mg/kg twice daily) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	unhealthy, children n = 236 Health Status: unhealthy Condition: HIV-1 Age Group: children Sex: unknown Population Size: 236 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf

Details

SMILES

InChI

DescriptionSources: https://www.drugbank.ca/drugs/DB00495Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.drugbank.ca/drugs/DB00495
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf

C_max

T_1/2

F_unbound

Drug as perpetrator