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Compound Detail

CHEMBL141

LAMIVUDINE
💊 Approved Drug
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💊 Approved Drug
Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1

Basic Information

ChEMBL ID CHEMBL141
Name LAMIVUDINE
Phase Approved
Structure Type MOL
InChI Key JTEGQNOMFQHVDC-NKWVEPMBSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1230

Known Names

3TC BCH 189, (-)- Epivir Epivir-hbv GR 109714X GR-109714X GR109714X Lamivudina Lamivudine Lamivudine component of /zidovudine teva Lamivudine component of cimduo Lamivudine component of combivir +15 more
24
Targets
371
Activities
3
Assay Types
30
PK Parameters
20
Publications
27
Known Names
20
Indications
5
Mechanisms

Molecular Properties

229.3
MW (Da)
-0.59
ALogP
7
HBA
2
HBD
90.4
PSA (Ų)
0.70
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vudine
USAN Year 1992

Extended Properties

Molecular Formula C8H11N3O3S
MW 229.26
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 1.46

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase
DNA inhibitor INHIBITOR DNA
DNA inhibitor INHIBITOR DNA
DNA inhibitor INHIBITOR DNA
DNA polymerase/reverse transcriptase inhibitor INHIBITOR DNA polymerase/reverse transcriptase

Indications

Autoimmune Diseases Hepatitis Hepatitis B Hepatitis B, Chronic Hepatitis B, Chronic HIV Infections HIV Infections Infections Inflammation Virus Diseases Acquired Immunodeficiency Syndrome AIDS-Associated Nephropathy Carcinoma, Hepatocellular Diarrhea Liver Cirrhosis Tuberculosis Colorectal Neoplasms Lymphoma Lymphoma, Non-Hodgkin Paraparesis, Tropical Spastic

ATC Classification

J05AF05
lamivudine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
metabolic toxicity
Country: United States
Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 280 meas. best 8.74
IC50 89 meas. best 8.7
Kd 2 meas. best 5.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 8.74 5.8641 1.8 166
Human immunodeficiency virus
CHEMBL613758
EC50 8.74 6.668 1.8 5
ADMET
CHEMBL612558
IC50 8.7 7.3533 2.0 3
Hepatitis B virus
CHEMBL613497
EC50 8.42 6.6554 3.8 65
HepG2
CHEMBL395
EC50 8.1 7.064 8.0 5
Hepatoma cell line
CHEMBL614821
EC50 8.0 8.0 10.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 8.0 5.82 10.0 6
ADMET
CHEMBL612558
EC50 8.0 7.46 10.0 4
PBMC
CHEMBL613107
EC50 7.94 7.755 11.6 2
Human immunodeficiency virus 1
CHEMBL378
IC50 7.66 6.4914 21.8 21
Hepatitis B virus
CHEMBL613497
IC50 7.6 6.073 25.0 23
HBV genotype D
CHEMBL612769
EC50 7.52 6.9425 30.0 4
Duck hepatitis B virus
CHEMBL613761
EC50 7.4 7.4 40.0 2
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
EC50 7.38 7.38 42.0 1
Hepatoblastoma cell line
CHEMBL614820
EC50 7.16 7.16 70.0 1
Anas sp.
CHEMBL612370
IC50 7.0 7.0 100.0 1
MT4
CHEMBL388
IC50 7.0 6.614 100.0 5
Human immunodeficiency virus 2
CHEMBL380
EC50 6.75 5.3544 180.0 9
Heat shock factor protein 1
CHEMBL5313
EC50 6.54 6.54 287.0 1
Core antigen
CHEMBL1075091
EC50 6.43 6.43 370.0 1
MT4
CHEMBL388
EC50 6.4 5.9533 400.0 3
Human gammaherpesvirus 4
CHEMBL613124
EC50 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
Kd 5.82 5.82 1510.0 1
Human alphaherpesvirus 1
CHEMBL377
IC50 5.66 5.66 2200.0 1
Unchecked
CHEMBL612545
EC50 4.95 4.72 11300.0 2
Human immunodeficiency virus 2
CHEMBL380
IC50 4.81 4.81 15500.0 2
Albumin
CHEMBL3253
Kd 4.36 4.36 44000.0 1
CCRF-CEM
CHEMBL382
IC50 4.3 4.3 50000.0 2
Voltage-gated L-type calcium channel
CHEMBL2095229
IC50 4.27 4.27 54200.0 1
Human adenovirus 2
CHEMBL613715
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10.42 pmol Homo sapiens
AUC 70.01 pmol Homo sapiens
AUC 65.19 pmol Homo sapiens
AUC 15700.0 ng.hr.mL-1 Homo sapiens
AUC 15500.0 ng.hr.mL-1 Homo sapiens
AUC 0.03531 ng.hr.mL-1 Homo sapiens
AUC 0.03691 ng.hr.mL-1 Homo sapiens
AUC 7800.0 ng.hr.mL-1 Homo sapiens
AUC 5420.0 ng.hr.mL-1 Homo sapiens
AUC 3710.0 ng.hr.mL-1 Homo sapiens
AUC 6540.0 ng.hr.mL-1 Homo sapiens
AUC 4440.0 ng.hr.mL-1 Homo sapiens
AUC 9800.0 ng.hr.mL-1 Homo sapiens
AUC 8100.0 ng.hr.mL-1 Homo sapiens
AUC 9100.0 ng.hr.mL-1 Homo sapiens
AUC 9.8 mg/L Homo sapiens
AUC 90523.31 ng.hr.mL-1 Macaca mulatta
AUC 0.0298 ng.hr.mL-1 Macaca mulatta
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 72.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Macaca
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 22.0 mL.min-1.kg-1 Canis lupus familiaris
CL 46.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 0.00076 nM Homo sapiens
Cmax 0.004424 nM Homo sapiens
Cmax 0.00484 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus EC50 = 1.8 nM 8.74 Anti-HIV-1 activity against human peripheral blood mononuclear (PBM) cells infec... 8423591
Human immunodeficiency virus 1 EC50 = 1.8 nM 8.74 Concentration required for antiviral activity in PBMC (human peripheral blood mo... 8410975
ADMET IC50 = 2.0 nM 8.7 Antiviral activity in PBM cells expressed as IC50 -
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against HIV-1 35792384
Hepatitis B virus EC50 = 3.8 nM 8.42 Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re... 32421339
HepG2 EC50 = 8.0 nM 8.1 In vitro effective concentration against hepatitis B virus was determined in 2.2... 9301659
Hepatitis B virus EC50 = 8.0 nM 8.1 Antiviral activity against Hepatitis B virus (HBV) in 2.2.15 cells 11052795
Hepatitis B virus EC50 = 8.87 nM 8.05 Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assess... 28682067
Hepatoma cell line EC50 = 10.0 nM 8.0 Antiviral activity against hepatitis B virus in human hepatoma cell line (2.2.15... -
ADMET EC50 = 10.0 nM 8.0 In vitro concentration required to inhibit the HIV-1 LA1 replication on PBMCs ce... 12852943
NON-PROTEIN TARGET EC50 = 10.0 nM 8.0 Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assess... 27748590
PBMC EC50 = 11.6 nM 7.94 Effective concentration to inhibit HIV-1 LAI cytopathicity in PBMC cells was det... 14971898
Human immunodeficiency virus 1 EC50 = 12.0 nM 7.92 Antiviral activity against HIV-1 Y181C mutant strain infected in human MT4 cells... 31767136
Hepatitis B virus EC50 = 18.0 nM 7.75 Antiviral activity against Hepatitis B virus ayw1 infected in human HepG2 2.2.15... 37611244
Human immunodeficiency virus 1 EC50 = 18.0 nM 7.75 Antiviral activity against wild type HIV-1 strain 3B infected in human MT4 cells... 31767136
Human immunodeficiency virus 1 EC50 = 19.0 nM 7.72 Antiviral activity against HIV-1 K103N mutant strain infected in human MT4 cells... 31767136
Human immunodeficiency virus 1 EC50 = 19.0 nM 7.72 Antiviral activity against HIV-1 E138K mutant strain infected in human MT4 cells... 31767136
Hepatitis B virus EC50 = 20.0 nM 7.7 Antiviral activity against HBV ayw1 infected in human HepG2.2.15 cells 36898483
Hepatitis B virus EC50 = 20.0 nM 7.7 Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assess... 28682067
Hepatitis B virus EC50 = 20.0 nM 7.7 Inhibition of HBV replication in 2.2.15 cells by DNA hybridization assay 17004726

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 62
18316521 10.1128/aac.01313-07 Human immunodeficiency virus 1 44
25847765 10.1016/j.ejmech.2015.03.056 Hepatitis B virus 43
17438047 10.1128/aac.01499-06 HBV genotype D 30
20516271 10.1128/aac.00306-10 Homo sapiens 28
17371827 10.1128/aac.01440-06 Hepatitis B virus 26
17242147 10.1128/aac.01013-06 Homo sapiens 26
17664328 10.1128/aac.01626-06 Homo sapiens 23
18676881 10.1128/aac.00654-08 Woodchuck hepatitis virus 22
21930377 10.1016/j.bmcl.2011.08.113 Hepatitis B virus 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
17488817 10.1073/pnas.0609883104 Hepatitis B virus 15
34890994 10.1016/j.bmc.2021.116531 Human immunodeficiency virus 1 15
19072694 10.1021/jm801418v Hepatitis B virus 14
30962085 10.1016/j.bmcl.2019.04.005 Hepatitis B virus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19289522 10.1128/aac.01559-08 Human immunodeficiency virus 1 13
22533850 10.1021/jm300492q Human immunodeficiency virus 1 13
19398648 10.1128/aac.00114-09 Hepatitis B virus 12

Data from ChEMBL 36 via Core Engine