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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

CNS Penetrant
2588
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

Originator

Approval Year

1995
203
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 2.0 nM [IC50]
Inhibitor
8504
 3.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther 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​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP3A4
2633
 no
MATE2
267
 no
OATP1B1
1095
 no
OATP1B3
970
 no
BCRP
985
 weak to no
OCT3
161
 weak to no
P-gp
1932
 weak to no
OCT1
656
 yes
OCT2
782
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
303
 not signifiicant
BCRP
697
 yes
MATE1
182
 yes
MATE2
98
 yes
OCT1
393
 yes
OCT2
434
 yes
P-gp
2052
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Novel 5-vinyl pyrimidine nucleosides with potent anti-hepatitis B virus activity.
2001-11-19
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.
2001-09-27
Anti-HBV specific beta-L-2'-deoxynucleosides.
2001-09-21
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.
2001-09-21
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.
2001-09-21
Safety and efficacy of adefovir dipivoxil in patients co-infected with HIV-1 and lamivudine-resistant hepatitis B virus: an open-label pilot study.
2001-09-01
Lamivudine treatment for hepatitis B reactivation in HBsAg carriers after organ transplantation: a 4-year experience.
2001-09
Specific inhibition of human immunodeficiency virus type 1 (HIV-1) integration in cell culture: putative inhibitors of HIV-1 integrase.
2001-09
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.
2001-09
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.
2001-09
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.
2001-08
Outcome of liver transplantation for hepatitis B: report of a single center's experience.
2001-08
Efficacy and tolerability of long-term therapy using high lamivudine doses for the treatment of chronic hepatitis B.
2001-07
Updated U.S. Public Health Service Guidelines for the Management of Occupational Exposures to HBV, HCV, and HIV and Recommendations for Postexposure Prophylaxis.
2001-06-29
Nelfinavir in expanded postexposure prophylaxis causing acute hepatitis with cholestatic features: two case reports.
2001-06
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.
2001-06
A multicenter study of lamivudine treatment in 33 patients with hepatitis B after liver transplantation.
2001-06
Cross-resistance testing of antihepadnaviral compounds using novel recombinant baculoviruses which encode drug-resistant strains of hepatitis B virus.
2001-06
Efavirenz-induced acute eosinophilic hepatitis.
2001-05
Hepatic decompensation associated with lamivudine: a case report and review of lamivudine-induced hepatotoxicity.
2001-05
4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro.
2001-05
Outcome of lamivudine resistant hepatitis B virus infection in liver transplant recipients in Singapore.
2001-04
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.
2001-04
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.
2001-04
From the Centers for Disease Control and Prevention. Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.
2001-03-27
The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host.
2001-03
Prenatal AZT or 3TC and mouse development of locomotor activity and hot-plate responding upon administration of the GABA(A) receptor agonist muscimol.
2001-02
Interferon therapy for flare-up of hepatitis B virus infection after emergence of lamivudine-induced YMDD motif mutant.
2001-02
Liver transplantation in Asian patients with chronic hepatitis B using lamivudine prophylaxis.
2001-02
A multicenter United States-Canadian trial to assess lamivudine monotherapy before and after liver transplantation for chronic hepatitis B.
2001-02
[Treatment of chronic viral hepatitis B with lamivudine].
2001-01-27
Antiviral L-nucleosides specific for hepatitis B virus infection.
2001-01
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.
2001
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.
2000-12-15
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000-12
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.
2000-11
Correlation between intracellular pharmacological activation of nucleoside analogues and HIV suppression in vitro.
2000-11
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.
2000-11
Clinical improvement in patients with decompensated liver disease caused by hepatitis B after treatment with lamivudine.
2000-11
Leucocytoclastic vasculitis and indinavir.
2000-11
Successful orthotopic liver transplantation for lamivudine-associated YMDD mutant hepatitis B virus.
2000-11
Synthesis and antiviral activity of oxaselenolane nucleosides.
2000-10-19
Efficacy of long-term lamivudine monotherapy in patients with hepatitis B e antigen-negative chronic hepatitis B.
2000-10
Lamivudine without HBIg for prevention of graft reinfection by hepatitis B: long-term follow-up.
2000-09-15
Sudden unexpected death as a consequence of indinavir-induced nephropathy. A case report.
2000-09
Acute exacerbation of chronic hepatitis B virus infection after withdrawal of lamivudine therapy.
2000-09
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.
2000-08
Beneficial effects of lamivudine in hepatitis B virus-related decompensated cirrhosis.
2000-08
Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs.
2000-07
Antiviral combination therapy for lamivudine-resistant hepatitis B reinfection after liver transplantation.
2000
Patents

Patents

05905082
3
US5047407
4

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
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 Wed Apr 02 09:59:14 GMT 2025
Edited
by admin
on Wed Apr 02 09:59:14 GMT 2025
Record UNII
77ANF82R6X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(±)-TRANS-LAMIVUDINE
Preferred Name English
LAMIVUDINE, (±)-TRANS-
Common Name English
4-AMINO-1-((2RS,5RS)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDIN-2(1H)-ONE
Systematic 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 Wed Apr 02 09:59:14 GMT 2025 , Edited by admin on Wed Apr 02 09:59:14 GMT 2025
PRIMARY
CAS
131086-22-1
Created by admin on Wed Apr 02 09:59:14 GMT 2025 , Edited by admin on Wed Apr 02 09:59:14 GMT 2025
PRIMARY
Related Record Type Details
Structure of LAMIVUDINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
NIH
NCATS
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