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	CH4O
Molecular Weight	32.0419
Charge	0
Count

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

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

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 70 Target ID: CHEMBL247 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf	Inhibitor 8504		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 8504		3.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2596
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf	Primary	Approved 8583	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 8583	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
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 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
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

AUC

Value	Dose	Co-administered	Analyte	Population
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 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
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

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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7751691/	Other AEs: Diarrhea, Abdominal discomfort... Other AEs: 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) Coughing (6 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961 MATE2 267 OCT3 159 BCRP 910 P-gp 1741 OCT1 620 OCT2 779	MATE1 182 MATE2 98 OCT1 393 OCT2 434 P-gp 2052 BCRP 697 CYP 303

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	no
MATE2 267	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	no
BCRP 985	inhibitor 4027 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 161	inhibitor 4027 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 1932	inhibitor 4027 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 656	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0	yes
OCT2 782	inhibitor 4027 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 303	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=21 Page: 21.0	not signifiicant
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
MATE1 182	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
MATE2 98	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
OCT1 393	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/product-information/dovato-epar-product-information_en.pdf#page=6 Page: 6.0	yes
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0	yes
P-gp 2052	substrate 4014 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
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
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

PubMed

Title	Date	PubMed
Effect of nucleoside analogs and non-nucleoside inhibitors of HIV-1 reverse transcriptase on cell-free virions.	1999	10226617
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
Utilization of transgenic mice replicating high levels of hepatitis B virus for antiviral evaluation of lamivudine.	1999 Jun	10389653
Efficacy of lamivudine in patients with hepatitis B e antigen-negative/hepatitis B virus DNA-positive (precore mutant) chronic hepatitis B. Lamivudine Precore Mutant Study Group.	1999 Mar	10051494
Severe anemia as a newly recognized side-effect caused by lamivudine.	1999 Nov 12	10563721
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
Antiviral combination therapy for lamivudine-resistant hepatitis B reinfection after liver transplantation.	2000	11112032
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.	2000 Dec	11145192
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.	2000 Dec 15	11141242
Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.	2000 Jan	10602742
Outcome of lamivudine resistant hepatitis B virus infection in the liver transplant recipient.	2000 Jan	10601065
A randomized, comparative study of lamivudine plus stavudine, with indinavir or nelfinavir, in treatment-experienced HIV-infected patients.	2000 Jan 28	10708286
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
Severe hypertension and renal atrophy associated with indinavir.	2000 Mar	10722466
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.	2000 Nov	11227993
An efficacy and cost-effectiveness analysis of combination hepatitis B immune globulin and lamivudine to prevent recurrent hepatitis B after orthotopic liver transplantation compared with hepatitis B immune globulin monotherapy.	2000 Nov	11084061
Clinical improvement in patients with decompensated liver disease caused by hepatitis B after treatment with lamivudine.	2000 Nov	11084057
Leucocytoclastic vasculitis and indinavir.	2000 Nov	11069541
Successful orthotopic liver transplantation for lamivudine-associated YMDD mutant hepatitis B virus.	2000 Nov	11054397
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 L-nucleosides specific for hepatitis B virus infection.	2001 Jan	11120971
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
Efficacy and tolerability of long-term therapy using high lamivudine doses for the treatment of chronic hepatitis B.	2001 Jul	11480792
Lamivudine and low-dose hepatitis B immune globulin for prophylaxis of hepatitis B reinfection after liver transplantation possible role of mutations in the YMDD motif prior to transplantation as a risk factor for reinfection.	2001 Jun	11451174
A multicenter study of lamivudine treatment in 33 patients with hepatitis B after liver transplantation.	2001 Jun	11443577
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
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.	2001 May-Jun	11572234
In vitro susceptibilities of wild-type or drug-resistant hepatitis B virus to (-)-beta-D-2,6-diaminopurine dioxolane and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.	2001 Sep	11502520
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

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 `Mon Mar 31 23:26:11 GMT 2025` Edited by `admin` on `Mon Mar 31 23:26:11 GMT 2025`
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

Preferred 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

Code System Code Type Description

PUBCHEM

76967759

Created by admin on Mon Mar 31 23:26:11 GMT 2025 , Edited by admin on Mon Mar 31 23:26:11 GMT 2025

PRIMARY

FDA UNII

PEM7E7C913

Created by admin on Mon Mar 31 23:26:11 GMT 2025 , Edited by admin on Mon Mar 31 23:26:11 GMT 2025

PRIMARY

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LAMIVUDINE

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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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 Health Status: unhealthy Age Group: 14.6 Sex: M+F 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Health Status: unhealthy Age Group: 7.6 Sex: M+F 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020564s37_020596s036lbl.pdf

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator