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Details

Stereochemistry RACEMIC
Molecular Formula C8H11N3O3S
Molecular Weight 229.2576
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAMIVUDINE, (+/-)-TRANS-

SMILES

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

InChI

InChIKey=JTEGQNOMFQHVDC-BQBZGAKWSA-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
Disappearance of hepatitis B virus core deletion mutants and successful combined kidney/liver transplantation in a patient treated with lamivudine.
1999
ddC- and 3TC-bis(SATE) monophosphate prodrugs overcome cellular resistance mechanisms to HIV-1 associated with cytidine kinase deficiency.
1999 Apr-May
Anti-HIV-1 activities of 1,3-dioxolane guanine and 2,6-diaminopurine dioxolane.
1999 Apr-May
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
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide.
1999 Aug
Abacavir and mycophenolic acid, an inhibitor of inosine monophosphate dehydrogenase, have profound and synergistic anti-HIV activity.
1999 Aug 15
Utilization of transgenic mice replicating high levels of hepatitis B virus for antiviral evaluation of lamivudine.
1999 Jun
Susceptibility of lamivudine-resistant hepatitis B virus to other reverse transcriptase inhibitors.
1999 Jun
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999 Jun 15
Liver transplantation for chronic hepatitis B infection with the use of combination lamivudine and low-dose hepatitis B immune globulin.
1999 Nov
Severe anemia as a newly recognized side-effect caused by lamivudine.
1999 Nov 12
In vitro induction of human immunodeficiency virus type 1 variants resistant to phosphoralaninate prodrugs of Z-methylenecyclopropane nucleoside analogues.
1999 Oct
Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.
1999 Oct
Inhibition of human immunodeficiency virus type 1 replication in acutely and chronically infected cells by EM2487, a novel substance produced by a Streptomyces species.
1999 Oct
Pretherapy alanine transaminase level as a determinant for hepatitis B e antigen seroconversion during lamivudine therapy in patients with chronic hepatitis B. Asian Hepatitis Lamivudine Trial Group.
1999 Sep
Antiviral combination therapy for lamivudine-resistant hepatitis B reinfection after liver transplantation.
2000
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
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.
2000 Aug
Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.
2000 Jan
Outcome of lamivudine resistant hepatitis B virus infection in the liver transplant recipient.
2000 Jan
A randomized, comparative study of lamivudine plus stavudine, with indinavir or nelfinavir, in treatment-experienced HIV-infected patients.
2000 Jan 28
Effects of extended lamivudine therapy in Asian patients with chronic hepatitis B. Asia Hepatitis Lamivudine Study Group.
2000 Jul
3-year suppression of HIV viremia with indinavir, zidovudine, and lamivudine.
2000 Jul 4
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.
2000 Jun 10
Selection and characterization of human immunodeficiency virus type 1 variants resistant to the (+) and (-) enantiomers of 2'-deoxy-3'-oxa-4'-thio-5-fluorocytidine.
2000 May
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
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
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
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
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
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
A multicenter study of lamivudine treatment in 33 patients with hepatitis B after liver transplantation.
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
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
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
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 Sat Jun 26 10:08:54 UTC 2021
Edited
by admin
on Sat Jun 26 10:08:54 UTC 2021
Record UNII
77ANF82R6X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAMIVUDINE, (+/-)-TRANS-
Common Name English
4-AMINO-1-((2RS,5RS)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDIN-2(1H)-ONE
Systematic Name English
(+/-)-TRANS-LAMIVUDINE
Common Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-((2R,5R)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, REL-
Systematic Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, TRANS-
Systematic Name English
LAMIVUDINE IMPURITY B RS [USP]
Common Name English
LAMIVUDINE IMPURITY B [EP]
Common Name English
LAMIVUDINE IMPURITY B [USP]
Common Name English
Code System Code Type Description
FDA UNII
77ANF82R6X
Created by admin on Sat Jun 26 10:08:55 UTC 2021 , Edited by admin on Sat Jun 26 10:08:55 UTC 2021
PRIMARY
PUBCHEM
6540852
Created by admin on Sat Jun 26 10:08:55 UTC 2021 , Edited by admin on Sat Jun 26 10:08:55 UTC 2021
PRIMARY
CAS
131086-22-1
Created by admin on Sat Jun 26 10:08:55 UTC 2021 , Edited by admin on Sat Jun 26 10:08:55 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP