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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O3S
Molecular Weight 229.256
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAMIVUDINE

SMILES

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

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 229.256
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
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
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide.
1999 Aug
Hypertensive crisis secondary to phenylpropanolamine interacting with triple-drug therapy for HIV prophylaxis.
1999 Jan
The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir: part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2-thioethyl)phosphotriester derivatives of acyclovir.
1999 Jan
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
Pyrido [1,2a] indole derivatives identified as novel non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1.
1999 Mar
Efficacy of lamivudine in patients with hepatitis B e antigen-negative/hepatitis B virus DNA-positive (precore mutant) chronic hepatitis B. Lamivudine Precore Mutant Study Group.
1999 Mar
Antiviral treatment for human immunodeficiency virus patients co-infected with hepatitis B virus: combined effect for both infections, an obtainable goal?
1999 May
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
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
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
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.
2000 Aug
Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs.
2000 Jul
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
Lamivudine after hepatitis B immune globulin is effective in preventing hepatitis B recurrence after liver transplantation.
2000 Jul
Combination low-dose hepatitis B immune globulin and lamivudine therapy provides effective prophylaxis against posttransplantation hepatitis B.
2000 Jul
Profound suppression of hepatitis B virus replication with lamivudine.
2000 Jul
In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.
2000 Jul
Steatosis-lactic acidosis syndrome associated with stavudine and lamivudine therapy.
2000 Jun 16
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.
2000 Nov
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
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
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
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 Mon Mar 31 21:28:23 GMT 2025
Edited
by admin
on Mon Mar 31 21:28:23 GMT 2025
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
DELSTRIGO COMPONENT LAMIVUDINE
Preferred 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
GR109714X
Code English
LAMIVUDINE [ORANGE BOOK]
Common Name English
Lamivudine [WHO-DD]
Common Name English
LAMIVUDINE TEVA
Brand Name English
lamivudine [INN]
Common Name English
LAMIVUDINE [EP IMPURITY]
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
BCH 189, (-)-
Code English
TRIUMEQ COMPONENT LAMIVUDINE
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 [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175462
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR04
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR05
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR02
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS LAMIVUDINE TEVA PHARMA B.V. (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR05
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS KIVEXA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR11
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR02
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR11
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/ZID)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR16
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NDF-RT N0000175656
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS ZEFFIX (AUTHORIZED: HEPTATIS B, CHRONIC)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR24
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR12
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR07
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NDF-RT N0000009947
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS EPIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
LIVERTOX NBK548553
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR01
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR13
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AR04
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS TRIUMEQ (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR01
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS LAMIVUDINE/ZIDOVUDINE TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ATC J05AF05
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AR07
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS COMBIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS TRIZIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/ZID)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS LAMIVUDINE TEVA (AUTHORIZED: HEPATITIS B, CHRONIC)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
EMA ASSESSMENT REPORTS DUTREBIS (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
WHO-VATC QJ05AF05
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
Code System Code Type Description
SMS_ID
100000085444
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
INN
6908
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
RXCUI
68244
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY RxNorm
CHEBI
63577
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
CAS
134678-17-4
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
FDA UNII
2T8Q726O95
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
LACTMED
Lamivudine
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LAMIVUDINE
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
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 Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL141
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
NCI_THESAURUS
C1471
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
HSDB
7155
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
USAN
DD-86
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID7023194
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
WIKIPEDIA
LAMIVUDINE
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
DRUG BANK
DB00709
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
NSC
760061
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
EVMPD
SUB08392MIG
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
MERCK INDEX
m6672
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY Merck Index
DAILYMED
2T8Q726O95
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
PUBCHEM
60825
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
DRUG CENTRAL
1539
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
RS_ITEM_NUM
1356836
Created by admin on Mon Mar 31 21:28:23 GMT 2025 , Edited by admin on Mon Mar 31 21:28:23 GMT 2025
PRIMARY
Related Record Type Details
Structure of LAMIVUDINE METHANOL SOLVATE
SOLVATE->ANHYDROUS
Structure of LAMIVUDINE METHANOL SOLVATE
SALT/SOLVATE -> PARENT
Structure of LAMIVUDINE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of LAMIVUDINE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE
TARGET -> INHIBITOR
HEPATITIS B VIRUS
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of LAMIVUDINE TRIPHOSPHATE
METABOLITE ACTIVE -> PARENT
Structure of LAMIVUDINE SULFOXIDE, (S)-
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of Troxacitabine
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-1,3-OXATHIOLANE-2-CARBOXYLIC ACID, CIS-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Cytosine
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LAMIVUDINE SULFOXIDE, (R)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LAMIVUDINE SULFOXIDE, (S)-
IMPURITY -> PARENT
Structure of LAMIVUDINE SULFOXIDE, (R)-
IMPURITY -> PARENT
Structure of URACIL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LAMIVUDINE, (±)-TRANS-
IMPURITY -> PARENT
Structure of 1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDINE-2,4(1H,3H)-DIONE, (2R,5S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of URACIL
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.
Structure of EMTRICITABINE
PARENT -> IMPURITY
Structure of 5-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-1,3-OXATHIOLANE-2-CARBOXYLIC ACID, CIS-
IMPURITY -> PARENT
Structure of Salicylic acid
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%).
Structure of 1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDINE-2,4(1H,3H)-DIONE, (2R,5S)-
IMPURITY -> PARENT
Structure of Salicylic acid
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Cytosine
IMPURITY -> PARENT
Structure of Cytosine
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%).
Structure of LAMIVUDINE, (+)-CIS-
IMPURITY -> PARENT
Structure of Troxacitabine
IMPURITY -> PARENT
Structure of LAMIVUDINE, (±)-TRANS-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of URACIL
IMPURITY -> PARENT
Structure of LAMIVUDINE, (+)-CIS-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Salicylic acid
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of LAMIVUDINE SULFOXIDE, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
Structure of LAMIVUDINE
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
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