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
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
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 |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdfhttps://pharmaffiliates.com/%C2%B1-trans-lamivudine/lamivudine-impurity-b-impurity/62787 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf | https://newdrugapprovals.org/2016/03/18/lamivudine/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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdfhttps://pharmaffiliates.com/%C2%B1-trans-lamivudine/lamivudine-impurity-b-impurity/62787 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020564s035,020596s034lbl.pdf | https://newdrugapprovals.org/2016/03/18/lamivudine/
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/22514580
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
Sources: http://www.thepharmaletter.com/article/lamivudine-positive-effects-in-hepatitis-bhttps://www.ncbi.nlm.nih.gov/pubmed/1929298
Curator's Comment: http://www.google.com/patents/US20030004175?hl=ru&cl=en
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL247 |
2.0 nM [IC50] | ||
Target ID: CHEMBL2362994 |
3.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EPIVIR Approved UseEPIVIR is a nucleoside analogue indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 (HIV-1) infection. Launch Date2004 |
|||
Primary | EPIVIR Approved UseEPIVIR-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 Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 μg/mL |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 |
Other AEs: Malaise and fatigue, Ear, nose and throat infection... Other AEs: Malaise and fatigue (25%) Sources: Ear, nose and throat infection (17%) Cough (8%) Headache (17%) Nausea and vomiting (8%) Ear, nose and throat infection (8%) |
10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Other AEs: Diarrhea, Abdominal discomfort... Other AEs: Diarrhea (9 patients) Sources: 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) |
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 |
Other AEs: Malaise and fatigue, Cough... Other AEs: Malaise and fatigue (27%) Sources: Cough (27%) Temperature regulation disorder NOS (27%) Nausea and vomiting (9%) Ear, nose and throat infection (18%) Ear disorder (9%) Pharyngitis (18%) |
150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Headache, Malaise and fatigue... Other AEs: Headache (35%) Sources: 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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 |
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 |
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 |
Arthralgia | 1 patient | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Nausea and vomiting | 1 patient | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Abdominal discomfort | 2 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Cognitive disorders | 2 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Oral lesion | 2 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Oral ulceration | 2 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Temperature regulation disorder | 2 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Muscle pain | 3 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Disorder sleep | 4 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Coughing | 6 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Headache | 6 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Malaise and fatigue | 6 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Diarrhea | 9 patients | 10 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 10 mg/kg, 2 times / day Route: oral Route: multiple Dose: 10 mg/kg, 2 times / day Sources: |
unhealthy, 37 years (range: 23-63 years) Health Status: unhealthy Age Group: 37 years (range: 23-63 years) Sources: |
Ear, nose and throat infection | 18% | 4 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 4 mg/kg, 2 times / day Route: oral Route: multiple Dose: 4 mg/kg, 2 times / day Sources: |
unhealthy, 7.6 |
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 |
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 |
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 |
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 |
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 |
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 |
Chills & fever | 10% | 150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy 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 Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0 |
no | |||
weak to no | ||||
weak to no | ||||
weak to no | ||||
Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200109001/340278000_30200AMX00001_I100_1.pdf#page=6 Page: 6.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
not signifiicant | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0 |
yes | |||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020564s039,020596s038lbl.pdf#page=19 Page: 19.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
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
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admin
on
Edited
Mon Mar 31 21:28:23 GMT 2025
by
admin
on
Mon Mar 31 21:28:23 GMT 2025
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Record UNII |
2T8Q726O95
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Record Status |
Validated (UNII)
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Record Version |
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Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
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Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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. | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
---|---|---|---|---|
|
SOLVATE->ANHYDROUS |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
|
||
|
TARGET ORGANISM->INHIBITOR |
|
||
|
TARGET -> INHIBITOR |
|
||
|
TARGET ORGANISM->INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT |
|
||
|
METABOLITE -> PARENT |
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity F. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity F (uracil) about 0.36.
|
||
|
PARENT -> IMPURITY |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity C. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity C (salicylic acid) about 2.6.
In the chromatogram obtained with solution (1): - the area of any peak corresponding to impurity C is not greater than that of the principal peak in the chromatogram obtained with solution (3) (0.1%).
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
Use the chromatogram supplied with lamivudine for system suitability RS and the chromatogram obtained with solutions (4) and (3) to identify the peaks due to impurity F. The impurity peaks are eluted at the following relative retention times with reference to lamivudine (retention time about 11 to 12 minutes): impurity E (cytosine) about 0.31.
In the chromatogram obtained with solution (1):- the area of any individual peak corresponding to impurity E, when multiplied by a correction factor of 0.6, is not greater than the area of the peak in the chromatogram obtained with solution (2) (0.1%).
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
Biological Half-life | PHARMACOKINETIC |
|
Intercellular PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
|
||