U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O3S
Molecular Weight 229.2576
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAMIVUDINE

SMILES

c1cn([C@]2([H])CS[C@]([H])(CO)O2)c(nc1=N)O

InChI

InChIKey=JTEGQNOMFQHVDC-NKWVEPMBSA-N
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H11N3O3S
Molecular Weight 229.2576
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment:: http://www.ncbi.nlm.nih.gov/pubmed/12766261

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1101081600000
Primary
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

1101081600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.3 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
12.4 μg × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.9 h
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

Doses

DosePopulationAdverse 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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
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:
unhealthy
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:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 14.6
Health Status: unhealthy
Age Group: 14.6
Sex: M+F
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 37 years (range: 23-63 years)
Health Status: unhealthy
Age Group: 37 years (range: 23-63 years)
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy, 7.6
Health Status: unhealthy
Age Group: 7.6
Sex: M+F
Sources:
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
weak to no
weak to no
weak to no
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Antiviral combination therapy for lamivudine-resistant hepatitis B reinfection after liver transplantation.
2000
Small molecule inhibitor of HIV-1 nuclear import suppresses HIV-1 replication in human lymphoid tissue ex vivo: a potential addition to current anti-HIV drug repertoire.
2000 Aug
Beneficial effects of lamivudine in hepatitis B virus-related decompensated cirrhosis.
2000 Aug
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000 Dec
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.
2000 Dec 15
Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs.
2000 Jul
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.
2000 Nov
Correlation between intracellular pharmacological activation of nucleoside analogues and HIV suppression in vitro.
2000 Nov
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
Clinical improvement in patients with decompensated liver disease caused by hepatitis B after treatment with lamivudine.
2000 Nov
Leucocytoclastic vasculitis and indinavir.
2000 Nov
Successful orthotopic liver transplantation for lamivudine-associated YMDD mutant hepatitis B virus.
2000 Nov
Efficacy of long-term lamivudine monotherapy in patients with hepatitis B e antigen-negative chronic hepatitis B.
2000 Oct
Synthesis and antiviral activity of oxaselenolane nucleosides.
2000 Oct 19
Sudden unexpected death as a consequence of indinavir-induced nephropathy. A case report.
2000 Sep
Acute exacerbation of chronic hepatitis B virus infection after withdrawal of lamivudine therapy.
2000 Sep
Lamivudine without HBIg for prevention of graft reinfection by hepatitis B: long-term follow-up.
2000 Sep 15
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.
2001
Outcome of lamivudine resistant hepatitis B virus infection in liver transplant recipients in Singapore.
2001 Apr
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
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.
2001 Apr
Anti-HBV specific beta-L-2'-deoxynucleosides.
2001 Apr-Jul
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.
2001 Apr-Jul
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.
2001 Apr-Jul
Successful lamivudine therapy for post-chemotherapeutic fulminant hepatitis B in a hepatitis B virus carrier with non-Hodgkin's lymphoma: case report and review of the literature.
2001 Aug
Outcome of liver transplantation for hepatitis B: report of a single center's experience.
2001 Aug
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
Interferon therapy for flare-up of hepatitis B virus infection after emergence of lamivudine-induced YMDD motif mutant.
2001 Feb
Liver transplantation in Asian patients with chronic hepatitis B using lamivudine prophylaxis.
2001 Feb
A multicenter United States-Canadian trial to assess lamivudine monotherapy before and after liver transplantation for chronic hepatitis B.
2001 Feb
Antiviral L-nucleosides specific for hepatitis B virus infection.
2001 Jan
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
[Treatment of chronic viral hepatitis B with lamivudine].
2001 Jan 27
Efficacy and tolerability of long-term therapy using high lamivudine doses for the treatment of chronic hepatitis B.
2001 Jul
Nelfinavir in expanded postexposure prophylaxis causing acute hepatitis with cholestatic features: two case reports.
2001 Jun
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
A multicenter study of lamivudine treatment in 33 patients with hepatitis B after liver transplantation.
2001 Jun
Cross-resistance testing of antihepadnaviral compounds using novel recombinant baculoviruses which encode drug-resistant strains of hepatitis B virus.
2001 Jun
Updated U.S. Public Health Service Guidelines for the Management of Occupational Exposures to HBV, HCV, and HIV and Recommendations for Postexposure Prophylaxis.
2001 Jun 29
The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host.
2001 Mar
Efavirenz-induced acute eosinophilic hepatitis.
2001 May
Hepatic decompensation associated with lamivudine: a case report and review of lamivudine-induced hepatotoxicity.
2001 May
4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro.
2001 May
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.
2001 May-Jun
Novel 5-vinyl pyrimidine nucleosides with potent anti-hepatitis B virus activity.
2001 Nov 19
Lamivudine treatment for hepatitis B reactivation in HBsAg carriers after organ transplantation: a 4-year experience.
2001 Sep
Specific inhibition of human immunodeficiency virus type 1 (HIV-1) integration in cell culture: putative inhibitors of HIV-1 integrase.
2001 Sep
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
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
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Pediatric dose should be calculated on body weight (kg) and should not exceed 300 mg daily.
Adults: 300 mg daily, administered as either 150 mg twice daily or 300 mg once daily.
Route of Administration: Oral
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 Fri Jun 25 21:02:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:24 UTC 2021
Record UNII
2T8Q726O95
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAMIVUDINE
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
TEMIXYS COMPONENT LAMIVUDINE
Common Name English
EPIVIR
Brand Name English
LAMIVUDINE [EP MONOGRAPH]
Common Name English
4-AMINO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDIN-2(1H)-ONE [WHO-IP]
Systematic Name English
EMTRICITABINE IMPURITY C [WHO-IP]
Common Name English
KIVEXA COMPONENT LAMIVUDINE
Common Name English
LAMIVUDINUM [WHO-IP LATIN]
Common Name English
GR-109714X
Code English
COMBIVIR COMPONENT LAMIVUDINE
Common Name English
LAMIVUDINE/ZIDOVUDINE TEVA COMPONENT LAMIVUDINE
Brand Name English
TRIZIVIR COMPONENT LAMIVUDINE
Brand Name English
VIROLAM
Common Name English
LAMIVUDINE [WHO-IP]
Common Name English
NSC-760061
Code English
LAMIVUDINE [USP-RS]
Common Name English
3TC
Code English
TELURA COMPONENT OF LAMIVUDINE
Common Name English
LAMIVUDINE [WHO-DD]
Common Name English
LAMIVUDINE COMPONENT OF TRIUMEQ
Brand Name English
LAMIVUDINE COMPONENT OF TRIZIVIR
Brand Name English
LAMIVUDINE COMPONENT OF DUTREBIS
Brand Name English
GR 109714X
Code English
LAMIVUDINE COMPONENT OF DELSTRIGO
Brand Name English
LAMIVUDINE COMPONENT OF COMBIVIR
Common Name English
DELSTRIGO COMPONENT LAMIVUDINE
Brand Name English
LAMIVUDINE COMPONENT OF TEMIXYS
Common Name English
LAMIVUDINE [ORANGE BOOK]
Common Name English
LAMIVUDINE TEVA
Brand Name English
LAMIVUDINE [INN]
Common Name English
ZEFFIX
Brand Name English
LAMIVUDINE [HSDB]
Common Name English
LAMIVUDINE [JAN]
Common Name English
LAMIVUDINE TEVA PHARMA B.V.
Brand Name English
(-)-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)CYTOSINE
Systematic Name English
LAMIVUDINE [EMA EPAR]
Common Name English
LAMIVUDINE COMPONENT OF EPZICOM
Common Name English
BCH 189, (-)-
Code English
TRIUMEQ COMPONENT LAMIVUDINE
Brand Name English
LAMIVUDINE COMPONENT OF LAMIVUDINE/ZIDOVUDINE TEVA
Brand Name English
LAMIVUDINE [MART.]
Common Name English
EPZICOM COMPONENT LAMIVUDINE
Common Name English
LAMIVUDINE [USAN]
Common Name English
LAMIVUDINE [VANDF]
Common Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, (2R-CIS)-
Common Name English
LAMIVUDINE [USP MONOGRAPH]
Common Name English
LAMIVUDINE [EP]
Common Name English
LAMIVUDINE [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175462
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR04
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR05
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR02
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NCI_THESAURUS C97452
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS LAMIVUDINE TEVA PHARMA B.V. (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR05
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS KIVEXA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR11
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR02
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR11
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/ZID)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR16
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NDF-RT N0000175656
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS ZEFFIX (AUTHORIZED: HEPTATIS B, CHRONIC)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR24
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR12
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR07
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NDF-RT N0000009947
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS EPIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
LIVERTOX 538
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR01
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR13
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AR04
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS TRIUMEQ (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR01
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS LAMIVUDINE/ZIDOVUDINE TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ATC J05AF05
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AR07
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS COMBIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS TRIZIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/ZID)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS LAMIVUDINE TEVA (AUTHORIZED: HEPATITIS B, CHRONIC)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
EMA ASSESSMENT REPORTS DUTREBIS (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
WHO-VATC QJ05AF05
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
Code System Code Type Description
INN
6908
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
RXCUI
68244
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY RxNorm
CAS
134678-17-4
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
FDA UNII
2T8Q726O95
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
LACTMED
Lamivudine
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LAMIVUDINE
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY Description: A white or almost white powder.Solubility: Soluble in water; sparingly soluble in methanol R; practically insoluble in acetone R. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Lamivudine should be kept in a well-closed container, protected from light. Additional information: Lamivudine may exhibit polymorphism. Definition: Lamivudine contains not less than 97.0% and not more than 103.0% of C8H11N3O3S, calculated with reference to the dried substance.
MESH
D019259
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL141
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
NCI_THESAURUS
C1471
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
HSDB
7155
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
EPA CompTox
134678-17-4
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
USP_CATALOG
1356836
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
LAMIVUDINE
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
DRUG BANK
DB00709
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
EVMPD
SUB08392MIG
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
MERCK INDEX
M6672
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY Merck Index
PUBCHEM
60825
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
DRUG CENTRAL
1539
Created by admin on Fri Jun 25 21:02:24 UTC 2021 , Edited by admin on Fri Jun 25 21:02:24 UTC 2021
PRIMARY
Related Record Type Details
INHIBITOR->TARGET ORGANISM
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
URINE
Related Record Type Details
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity F. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity F (uracil) about 0.36.
PARENT -> IMPURITY
IMPURITY -> PARENT
IMPURITY -> PARENT
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity C. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity C (salicylic acid) about 2.6. In the chromatogram obtained with solution (1): - the area of any peak corresponding to impurity C is not greater than that of the principal peak in the chromatogram obtained with solution (3) (0.1%).
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity F. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity E (cytosine) about 0.31. In the chromatogram obtained with solution (1):- the area of any individual peak corresponding to impurity E, when multiplied by a correction factor of 0.6, is not greater than the area of the peak in the chromatogram obtained with solution (2) (0.1%).
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Intercellular
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC