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Details

Stereochemistry RACEMIC
Molecular Formula C8H11N3O3S
Molecular Weight 229.256
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

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

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2CS[C@@H](CO)O2

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 229.256
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment: Known to be CNS penetrant in rat, guinea pig. Human data not available. http://www.ncbi.nlm.nih.gov/pubmed/9593963 http://www.ncbi.nlm.nih.gov/pubmed/18042828 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

1.10108161E12
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

1.10108161E12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 14.6
Sex: M+F
Population Size: 12
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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)
n = 14
Health Status: unhealthy
Condition: HIV infection
Age Group: 37 years (range: 23-63 years)
Population Size: 14
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
n = 11
Health Status: unhealthy
Condition: Chronic hepatitis B
Age Group: 7.6
Sex: M+F
Population Size: 11
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
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Decreased appetite 10%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Dizziness 10%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Insomnia disorder 11%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Musculoskeletal pain 12%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Neuropathy 12%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Nausea and vomiting 13%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Cough 18%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Diarrhea 18%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Nasal disorders NEC 20%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Malaise and fatigue 27%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Nausea 33%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Headache 35%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Arthralgia 5%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Dyspepsia 5%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Abdominal cramps 6%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Myalgia 8%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Abdominal pain 9%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Depressive disorders 9%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
Skin rash 9%
150 mg 1 times / day multiple, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Co-administed with::
zidovudine(200 mg; 3/day)
Sources:
unhealthy
n = 251
Health Status: unhealthy
Condition: HIV-1 infection
Population Size: 251
Sources:
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
Liver transplantation for chronic hepatitis B infection with the use of combination lamivudine and low-dose hepatitis B immune globulin.
1999 Nov
Long-term incidence of hepatitis B virus resistance to lamivudine in human immunodeficiency virus-infected patients.
1999 Nov
Role of lamivudine in the treatment of chronic hepatitis B virus infection.
1999 Oct
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
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
Prevention of de novo hepatitis B infection in recipients of hepatic allografts from anti-HBc positive donors.
1999 Oct 15
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
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
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000 Dec
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
Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs.
2000 Jul
Effects of extended lamivudine therapy in Asian patients with chronic hepatitis B. Asia Hepatitis Lamivudine Study Group.
2000 Jul
Management of hepatitis B in China.
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
Steatosis-lactic acidosis syndrome associated with stavudine and lamivudine therapy.
2000 Jun 16
Antiviral activity of 2'-deoxy-3'-oxa-4'-thiocytidine (BCH-10652) against lamivudine-resistant human immunodeficiency virus type 1 in SCID-hu Thy/Liv mice.
2000 Mar
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
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
Leucocytoclastic vasculitis and indinavir.
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
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
A multicenter United States-Canadian trial to assess lamivudine monotherapy before and after liver transplantation for chronic hepatitis B.
2001 Feb
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
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
Cross-resistance testing of antihepadnaviral compounds using novel recombinant baculoviruses which encode drug-resistant strains of hepatitis B virus.
2001 Jun
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. Dosage of this product is for HIV-1 and not for HBV
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 Dec 16 18:02:23 UTC 2023
Edited
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on Sat Dec 16 18:02:23 UTC 2023
Record UNII
77ANF82R6X
Record Status Validated (UNII)
Record Version
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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
LAMIVUDINE IMPURITY B [USP IMPURITY]
Common Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, TRANS-
Systematic Name English
LAMIVUDINE IMPURITY B [EP IMPURITY]
Common Name English
Code System Code Type Description
FDA UNII
77ANF82R6X
Created by admin on Sat Dec 16 18:02:24 UTC 2023 , Edited by admin on Sat Dec 16 18:02:24 UTC 2023
PRIMARY
PUBCHEM
6540852
Created by admin on Sat Dec 16 18:02:24 UTC 2023 , Edited by admin on Sat Dec 16 18:02:24 UTC 2023
PRIMARY
CAS
131086-22-1
Created by admin on Sat Dec 16 18:02:24 UTC 2023 , Edited by admin on Sat Dec 16 18:02:24 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP