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 8146	24.0 µM [IC50]
MCF7 21 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12893431	Inhibitor 8146	22.0 µM [IC50]
Human immunodeficiency virus type 1 reverse transcriptase 47 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 8146	0.01 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 145 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019910s033lbl.pdf	Primary		Approved 8307	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 5.43023989E11

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 1670 inhibitor 1532	substrate 985 inhibitor 1695	inhibitor 1789	inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT 32 P-gp 1401 BCRP 678 OAT3 625 MRP2 363 MRP3 156 MRP4 202 CYP1A2 1463 CYP2A6 670 CYP2C19 1410 CYP2E1 846 OAT1 584 OAT2 144 OAT4 145 OCT1 498 OCT2 630 OCTN2 66 OATP1B1 770 OATP1B3 691 OATP2B1 121 MRP1 106	UGT 183 UGT1A1 417 UGT1A3 421 UGT1A4 345 UGT1A6 306 UGT1A7 235 UGT1A9 378 UGT1A10 289 UGT2B4 248 UGT2B7 387 UGT2B15 202 UGT2B17 212 CYP2A6 510 CYP2C8 670 CYP2C19 955 P-gp 1491 MRP4 75 MRP5 39 BCRP 545 OAT1 314 OAT2 111 OAT3 328 OAT4 76 OCT2 336

Drug as perpetrator

Target	Modality	Activity
BCRP 751	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/28712845/, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 <400 uM]
P-gp 1588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/28712845/	no [IC50 <500 uM]
CYP1A2 1620	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2A6 702	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C19 1484	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C9 1747	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2D6 1826	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI5In19	no [IC50 >10 uM]
CYP2E1 929	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP3A4 1857	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI5In19	no [IC50 >10 uM]
MRP2 452	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 206	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 235	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP1 170	inhibitor 3185 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 124	inhibitor 3185 Sources: https://pubs.acs.org/doi/10.1021/jm300212s	no
OCT1 513	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OCT2 631	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OCTN2 71	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/10525100/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjkzIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	no
OAT3 627	inhibitor 3185 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 55	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/1907149/	yes [Ki 1200 uM]
OAT1 588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OAT2 146	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTU1NzExIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OAT4 145	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyOSJ9fQ%3D%3D	yes
OATP1B1 785	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 700	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT2B7 387	substrate 3264 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 202	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	minor
UGT2B4 248	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	minor
OCT2 336	substrate 3264 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 417	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A4 345	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A6 306	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A7 235	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT1A9 378	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
UGT2B17 212	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/12920168/	no
OAT3 328	substrate 3264 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 76	substrate 3264 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 183	substrate 3264 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 111	substrate 3264 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 314	substrate 3264 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 545	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/18464048/, https://pubmed.ncbi.nlm.nih.gov/15345326/	yes
CYP2A6 510	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C19 955	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C8 670	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP2C9 985	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP3A4 1670	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
MRP4 75	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/18535159/	yes
MRP5 39	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/18535159/	yes
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/19472342/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1603	inhibitor 1584 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
In vitro anti-hepatitis B virus activities of 5"-O-myristoyl analogue derivatives of 3"-fluoro-2",3"-dideoxythymidine (FLT) and 3"-azido-2",3"-dideoxythymidine (AZT).	1998 Sep-Dec	10948398
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 anti-HIV activity of some S-acyl-2-thioethyl (SATE) phosphoramidate derivatives of 3'-azido-2',3'-dideoxythymidine.	1999 Apr-May	10432724
Antiviral nucleoside drug delivery via amino acid phosphoramidates.	1999 Apr-May	10432709
Antiviral activity and resistance profile of phosphazid--a novel prodrug of AZT.	1999 Apr-May	10432707
Anti-HIV-1 activities of 1,3-dioxolane guanine and 2,6-diaminopurine dioxolane.	1999 Apr-May	10432704
"Mixed inhibitors" of HIV-reverse transcriptase: synthesis and antiviral activity.	1999 Apr-May	10432669
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
Synthesis and anti-HIV activity of 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazines (TTDs): a new family of HIV-1 specific non-nucleoside reverse transcriptase inhibitors.	1999 Dec	10658585
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
Inhibition of beta-globin gene expression by 3'-azido-3'-deoxythymidine in human erythroid progenitor cells.	1999 Dec 31	10651068
Relation of peripheral neuropathy to HIV treatment in four randomized clinical trials including didanosine.	1999 Jul	10463516
Zidovudine-induced experimental myopathy: dual mechanism of mitochondrial damage.	1999 Jul 1	10475107
Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents.	1999 Jul 15	10411486
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
Utilization of transgenic mice replicating high levels of hepatitis B virus for antiviral evaluation of lamivudine.	1999 Jun	10389653
WHI-05, a novel bromo-methoxy substituted phenyl phosphate derivative of zidovudine, is a dual-action spermicide with potent anti-HIV activity.	1999 May	10494486
Prolactin exerts hematopoietic growth-promoting effects in vivo and partially counteracts myelosuppression by azidothymidine.	1999 May	10340396
Synthesis, characterization and preclinical formulation of a dual-action phenyl phosphate derivative of bromo-methoxy zidovudine (compound WHI-07) with potent anti-HIV and spermicidal activities.	1999 May	10338365
Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217.	1999 Nov	10628806
Multiorgan transplacental and neonatal carcinogenicity of 3'-azido-3'-deoxythymidine in mice.	1999 Nov 15	10558926
In vitro induction of human immunodeficiency virus type 1 variants resistant to phosphoralaninate prodrugs of Z-methylenecyclopropane nucleoside analogues.	1999 Oct	10508028
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
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group.	1999 Oct 1	10843527
Genotoxicity of 3'-azido-3'-deoxythymidine in the human lymphoblastoid cell line, TK6: relationships between DNA incorporation, mutant frequency, and spectrum of deletion mutations in HPRT.	1999 Oct 19	10526209
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
Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus.	1999 Sep	10574178
Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents.	1999 Sep	10530939
N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1.	1999 Sep 20	10509923
The anti-HIV pseudopeptide HB-19 forms a complex with the cell-surface-expressed nucleolin independent of heparan sulfate proteoglycans.	1999 Sep 24	10488134
Persistent mitochondrial dysfunction and perinatal exposure to antiretroviral nucleoside analogues.	1999 Sep 25	10509500
Prophylactic contraceptives for HIV/AIDS.	1999 Sep-Oct	10582788
Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors.	2000 Apr 10	10777142
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.	2000 Aug	10898683
Cardiac dysfunction occurs in the HIV-1 transgenic mouse treated with zidovudine.	2000 Feb	10701688
Cytochrome c oxidase deficiency in the muscle of patients with zidovudine myopathy is segmental and affects both mitochondrial DNA- and nuclear DNA-encoded subunits.	2000 Jul	10912924
3-year suppression of HIV viremia with indinavir, zidovudine, and lamivudine.	2000 Jul 4	10877738
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.	2000 Jun 10	10875608
Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents.	2000 Mar	10819438
Syntheses of oxanosine and carbocyclic oxanosine derivatives as anti-HIV agents.	2000 Mar	10819305
Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release.	2000 Mar	10746882
Spiropentane mimics of nucleosides: analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity.	2000 Mar 10	10814087
Variable sensitivity of CCR5-tropic human immunodeficiency virus type 1 isolates to inhibition by RANTES analogs.	2000 May	10775626
3'-azido-3'-deoxythimidine (AZT) is glucuronidated by human UDP-glucuronosyltransferase 2B7 (UGT2B7).	2000 May	10772627
Anti-human immunodeficiency virus activity of novel aminoglycoside-arginine conjugates at early stages of infection.	2000 May 1	10791873

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 `Sun Dec 18 18:21:20 UTC 2022` Edited by `admin` on `Sun Dec 18 18:21:20 UTC 2022`
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)