LAMIVUDINE METHANOL SOLVATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	5C8H11N3O3S.CH4O
Molecular Weight	1178.323
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LAMIVUDINE METHANOL SOLVATE

Structure Search

SMILES

CO.NC1=NC(=O)N(C=C1)[C@@H]2CS[C@H](CO)O2.NC3=NC(=O)N(C=C3)[C@@H]4CS[C@H](CO)O4.NC5=NC(=O)N(C=C5)[C@@H]6CS[C@H](CO)O6.NC7=NC(=O)N(C=C7)[C@@H]8CS[C@H](CO)O8.NC9=NC(=O)N(C=C9)[C@@H]%10CS[C@H](CO)O%10

InChI

InChIKey=WSZXHYMIYANYOU-WSXGJQPVSA-N

InChI=1S/5C8H11N3O3S.CH4O/c5*9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6;1-2/h5*1-2,6-7,12H,3-4H2,(H2,9,10,13);2H,1H3/t5*6-,7+;/m00000./s1

HIDE SMILES / InChI

Molecular Formula	C8H11N3O3S
Molecular Weight	229.256
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	CH4O
Molecular Weight	32.0419
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdfhttps://pharmaffiliates.com/%C2%B1-trans-lamivudine/lamivudine-impurity-b-impurity/62787 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf | https://newdrugapprovals.org/2016/03/18/lamivudine/
Curator's Comment: Description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00709 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2df7349c-f5d7-47b5-d29b-1b6b31985591

Lamivudine is a reverse transcriptase inhibitor used alone or in combination with other classes of anti-human immunodeficiency virus (HIV) drugs in the treatment of HIV infection. This molecule has two stereo-centers, thus giving rise to four stereoisomers: (+/-)-cis-lamivudine and (+/-)-trans-lamivudine. The latter is considered to be impurity of the pharmaceutically active isomer, (-)-cis-lamivudine.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 67 Target ID: CHEMBL247 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf	Inhibitor 8297		2.0 nM [IC50]
DNA polymerase/reverse transcriptase 10 Target ID: CHEMBL2362994 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021003s015,021004s015lbl.pdf	Inhibitor 8297		3.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
HIV-1 infection 151 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf	Primary	Approved 8429	EPIVIR Approved Use EPIVIR is a nucleoside analogue indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 (HIV-1) infection. Launch Date 2004
Chronic hepatitis B 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021003s015,021004s015lbl.pdf	Primary	Approved 8429	EPIVIR Approved Use EPIVIR-HBV is a nucleoside analogue reverse transcriptase inhibitor indicated for the treatment of chronic hepatitis B virus infection associated with evidence of hepatitis B viral replication and active liver inflammation Launch Date 2004

C_max

Value	Dose	Co-administered	Analyte	Population
3.3 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29150845	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		LAMIVUDINE blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAMIVUDINE unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
12.4 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29150845	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		LAMIVUDINE blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.53 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAMIVUDINE unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29150845	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		LAMIVUDINE blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	Other AEs: Malaise and fatigue, Ear, nose and throat infection... Other AEs: Malaise and fatigue (25%) Ear, nose and throat infection (17%) Cough (8%) Headache (17%) Nausea and vomiting (8%) Ear, nose and throat infection (8%) Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	Other AEs: Coughing, Diarrhea... Other AEs: Coughing (6 patients) Diarrhea (9 patients) Abdominal discomfort (2 patients) Nausea and vomiting (1 patient) Malaise and fatigue (6 patients) Headache (6 patients) Disorder sleep (4 patients) Cognitive disorders (2 patients) Oral ulceration (2 patients) Oral lesion (2 patients) Muscle pain (3 patients) Arthralgia (1 patient) Temperature regulation disorder (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	Other AEs: Malaise and fatigue, Cough... Other AEs: Malaise and fatigue (27%) Cough (27%) Temperature regulation disorder NOS (27%) Nausea and vomiting (9%) Ear, nose and throat infection (18%) Ear disorder (9%) Pharyngitis (18%) Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	Other AEs: Headache, Malaise and fatigue... Other AEs: Headache (35%) Malaise and fatigue (27%) Chills & fever (10%) Nausea (33%) Diarrhea (18%) Nausea and vomiting (13%) Decreased appetite (10%) Abdominal pain (9%) Abdominal cramps (6%) Dyspepsia (5%) Neuropathy (12%) Insomnia disorder (11%) Dizziness (10%) Depressive disorders (9%) Nasal disorders NEC (20%) Cough (18%) Skin rash (9%) Musculoskeletal pain (12%) Myalgia (8%) Arthralgia (5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 OATP1B3 706 MATE2 263 OCT3 150 BCRP 699 P-gp 1461 OCT1 512 OCT2 647	MATE1 135 MATE2 96 OCT1 327 OCT2 355 P-gp 1537 BCRP 561 CYP 270

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
MATE2 263	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
BCRP 773	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	weak to no
OCT3 150	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	weak to no
P-gp 1650	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	weak to no
OCT1 543	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	yes
OCT2 648	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	yes

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	not signifiicant
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
MATE1 135	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
MATE2 96	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
OCT1 327	substrate 3367 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=6 Page: 6.0	yes
OCT2 355	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63577	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63577
ChemicalBook	CB1290608	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1290608
MolPort	MolPort-002-507-347	https://www.molport.com/shop/molecule-link/MolPort-002-507-347
Selleck Chemicals	Lamivudine(Epivir)	http://www.selleckchem.com/products/Lamivudine(Epivir).html
ZINC	ZINC000000012346	http://zinc15.docking.org/substances/ZINC000000012346
eMolecules	1987423	https://www.emolecules.com/cgi-bin/more?vid=1987423
eMolecules	2726078	https://www.emolecules.com/cgi-bin/more?vid=2726078
eMolecules	31588897	https://www.emolecules.com/cgi-bin/more?vid=31588897

PubMed

Title	Date	PubMed
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
Hypertensive crisis secondary to phenylpropanolamine interacting with triple-drug therapy for HIV prophylaxis.	1999 Jan	10320127
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
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
Additional interferon alpha for lamivudine resistant hepatitis B infection after liver transplantation: a preliminary report.	2000 Apr 27	10836394
Lamivudine, adefovir and tenofovir exhibit long-lasting anti-hepatitis B virus activity in cell culture.	2000 Jan	10718947
Differential transport of cytosine-containing nucleosides by recombinant human concentrative nucleoside transporter protein hCNT1.	2000 Jan-Feb	10772724
Potentiation of the anti-HIV activity of zalcitabine and lamivudine by a CTP synthase inhibitor, 3-deazauridine.	2000 Jan-Feb	10772721
Lamivudine after hepatitis B immune globulin is effective in preventing hepatitis B recurrence after liver transplantation.	2000 Jul	10915164
Combination low-dose hepatitis B immune globulin and lamivudine therapy provides effective prophylaxis against posttransplantation hepatitis B.	2000 Jul	10915163
Profound suppression of hepatitis B virus replication with lamivudine.	2000 Jul	10861648
In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.	2000 Jul	10858331
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.	2000 Nov	11227993
Lamivudine without HBIg for prevention of graft reinfection by hepatitis B: long-term follow-up.	2000 Sep 15	11003363
Outcome of lamivudine resistant hepatitis B virus infection in liver transplant recipients in Singapore.	2001 Apr	11288740
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.	2001 Apr	11264389
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.	2001 Apr	11257017
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.	2001 Apr-Jul	11563039
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.	2001 Apr-Jul	11562951
Prenatal AZT or 3TC and mouse development of locomotor activity and hot-plate responding upon administration of the GABA(A) receptor agonist muscimol.	2001 Feb	11243490
Interferon therapy for flare-up of hepatitis B virus infection after emergence of lamivudine-induced YMDD motif mutant.	2001 Feb	11227671
From the Centers for Disease Control and Prevention. Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.	2001 Jan 24-31	11263401
Cross-resistance testing of antihepadnaviral compounds using novel recombinant baculoviruses which encode drug-resistant strains of hepatitis B virus.	2001 Jun	11353615
The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host.	2001 Mar	11244173
Hepatic decompensation associated with lamivudine: a case report and review of lamivudine-induced hepatotoxicity.	2001 May	11374710
4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro.	2001 May	11302824
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.	2001 Sep	11448730
Safety and efficacy of adefovir dipivoxil in patients co-infected with HIV-1 and lamivudine-resistant hepatitis B virus: an open-label pilot study.	2001 Sep 1	11551579

Patents

Sample Use Guides

In Vivo Use Guide

Adults: 300 mg daily, administered as either 150 mg twice daily or 300 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

The antiviral activity of lamivudine against HIV-1 was assessed in a number of cell lines including monocytes and fresh human peripheral blood lymphocytes (PBMCs) using standard susceptibility assays. EC50 values were in the range of 0.003 to 15 microM (1 microM = 0.23 mcg per mL).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:46:31 GMT 2023` Edited by `admin` on `Sat Dec 16 10:46:31 GMT 2023`
Record UNII	PEM7E7C913
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAMIVUDINE METHANOL SOLVATE

Common Name

English

4-AMINO-1-((2R, 5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5YL)PYRIMIDIN-2(1H)-ONE, METHANOL SOLVATE (5:1)

Systematic Name

English

LAMIVUDINE (AS METHANOL SOLVATE)

Common Name

English

4-AMINO-1-((2R, 5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5YL)PYRIMIDIN-2(1H)-ONE, METHANOL SOLVATE

Common Name

English

Code System Code Type Description

PUBCHEM

76967759

Created by admin on Sat Dec 16 10:46:31 GMT 2023 , Edited by admin on Sat Dec 16 10:46:31 GMT 2023

PRIMARY

FDA UNII

PEM7E7C913

Created by admin on Sat Dec 16 10:46:31 GMT 2023 , Edited by admin on Sat Dec 16 10:46:31 GMT 2023

PRIMARY

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ACTIVE MOIETY

AE	Significance	Dose	Population
Ear, nose and throat infection	17%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Headache	17%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Malaise and fatigue	25%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Cough	8%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Ear, nose and throat infection	8%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Nausea and vomiting	8%	100 mg 1 times / day multiple, oral Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 14.6 n = 12 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 14.6 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Arthralgia	1 patient	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Nausea and vomiting	1 patient	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Abdominal discomfort	2 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Cognitive disorders	2 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Oral lesion	2 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Oral ulceration	2 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Temperature regulation disorder	2 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Muscle pain	3 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Disorder sleep	4 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Coughing	6 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Headache	6 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Malaise and fatigue	6 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Diarrhea	9 patients	10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	unhealthy, 37 years (range: 23-63 years) n = 14 Health Status: unhealthy Condition: HIV infection Age Group: 37 years (range: 23-63 years) Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/
Ear, nose and throat infection	18%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Pharyngitis	18%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Cough	27%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Malaise and fatigue	27%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Temperature regulation disorder NOS	27%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Ear disorder	9%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Nausea and vomiting	9%	4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/	unhealthy, 7.6 n = 11 Health Status: unhealthy Condition: Chronic hepatitis B Age Group: 7.6 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/10681323/
Chills & fever	10%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Decreased appetite	10%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Dizziness	10%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Insomnia disorder	11%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Musculoskeletal pain	12%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Neuropathy	12%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Nausea and vomiting	13%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Cough	18%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Diarrhea	18%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Nasal disorders NEC	20%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Malaise and fatigue	27%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Nausea	33%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Headache	35%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Arthralgia	5%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Dyspepsia	5%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Abdominal cramps	6%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Myalgia	8%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Abdominal pain	9%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Depressive disorders	9%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf
Skin rash	9%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: zidovudine(200 mg; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy n = 251 Health Status: unhealthy Condition: HIV-1 infection Population Size: 251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

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Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

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Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

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Drug as perpetrator