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Compound Detail

CHEMBL885

EMTRICITABINE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(=O)n([C@@H]2CS[C@H](CO)O2)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL885
Name EMTRICITABINE
Phase Approved
Structure Type MOL
InChI Key XQSPYNMVSIKCOC-NTSWFWBYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL341421

Known Names

(-)-emtricitabine (-)-FTC 524-W-91 524W91 BW-524W91 Coviracil Emtricitabina Emtricitabine Emtricitabine component of atripla Emtricitabine component of biktarvy Emtricitabine component of complera Emtricitabine component of descovy +10 more
7
Targets
46
Activities
3
Assay Types
7
PK Parameters
20
Publications
22
Known Names
13
Indications
1
Mechanisms

Molecular Properties

247.2
MW (Da)
-0.46
ALogP
7
HBA
2
HBD
90.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2003
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Stem -citabine
USAN Year 1998

Extended Properties

Molecular Formula C8H10FN3O3S
MW 247.25
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness 0.70

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 ✓ ✓

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome Hepatitis B, Chronic Hepatitis B, Chronic Infections Severe Acute Respiratory Syndrome Liver Cirrhosis, Biliary Multiple Sclerosis Hepatitis C Insulin Resistance Tuberculosis

ATC Classification

J05AF09
emtricitabine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

EC50 37 meas. best 8.89
IC50 8 meas. best 9.0
Kd 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.0 8.3114 1.0 7
Human immunodeficiency virus
CHEMBL613758
 EC50 8.89 8.89 1.3 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.68 6.1357 2.1 30
Unchecked
CHEMBL612545
 EC50 8.26 6.7133 5.5 3
HepG2
CHEMBL395
 EC50 7.52 7.52 30.0 1
Hepatitis B virus
CHEMBL613497
 EC50 7.0 7.0 100.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.3 6.3 500.0 1
HepG2
CHEMBL395
 IC50 4.56 4.56 27700.0 1
Albumin
CHEMBL3253
 Kd 4.36 4.36 44000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 93.0 % Homo sapiens
F 93.0 % Homo sapiens
F 60.0 % Homo sapiens
F 58.0 % Rattus norvegicus
F 58.0 % Mus musculus
F 58.0 % Macaca fascicularis
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 1.0 nM 9.0 Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of... 19596885
Human immunodeficiency virus 1 IC50 = 1.0 nM 9.0 Antiviral activity against HIV-1 infected in lymphoblastoid cell (unknown origin... 37393791
Human immunodeficiency virus 1 IC50 = 1.0 nM 9.0 Antiviral activity against HIV-1 infected in human HeLa-MAGI-CCR5 cells 37393791
Human immunodeficiency virus 1 IC50 = 1.0 nM 9.0 Antiviral activity against HIV-1 infected in PBMC (unknown origin) 37393791
Human immunodeficiency virus EC50 = 1.3 nM 8.89 Anti-HIV-1 activity against human peripheral blood mononuclear (PBM) cells infec... 8423591
Human immunodeficiency virus 1 EC50 = 2.1 nM 8.68 Anti-HIV activity against HIV1 Bal infected in human PBMC assessed as inhibition... 34795872
Unchecked EC50 = 5.5 nM 8.26 Anti-HIV activity against HIV1 3B infected in human PBMC assessed as inhibition ... 34795872
Human immunodeficiency virus 1 EC50 = 8.0 nM 8.1 Antiviral activity against HIV-1 LAV 34213340
Human immunodeficiency virus 1 IC50 = 9.0 nM 8.05 Antiviral activity against HIV-1 LAV infected in human CEM cells 37393791
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inh... 32515595
Human immunodeficiency virus 1 EC50 = 16.0 nM 7.8 Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as in... 32515595
Human immunodeficiency virus 1 EC50 = 30.0 nM 7.52 Antiviral activity against wild type HIV1 97USSN54 infected in human CEM-GXR cel... 34795872
Human immunodeficiency virus 1 EC50 = 30.0 nM 7.52 Antiviral activity against wild type HIV1 NL4-3 infected in human CEM-GXR cells ... 34795872
HepG2 EC50 = 30.0 nM 7.52 Inhibition of hepatitis B virus replication in the HepAD38 cell line. 11128652
Human immunodeficiency virus 1 EC50 = 40.0 nM 7.4 Antiviral activity against subtype B X4 tropic HIV1 3B infected in GFP-positive ... 26878150
Human immunodeficiency virus 1 IC50 = 44.0 nM 7.36 Antiviral activity against HIV1 infected in human MT2 cells assessed as inhibiti... 19596885
Human immunodeficiency virus 1 EC50 = 46.0 nM 7.34 Antiviral activity against HIV2 ROD infected in human TK-deficient CEM/TK(-) cel... 32515595
Hepatitis B virus EC50 = 100.0 nM 7.0 Antiviral activity against HBV in HepG2.2.15 cells assessed as decrease in extra... 17404006
Human immunodeficiency virus 1 IC50 = 170.0 nM 6.77 Antiviral activity against HIV1 infected in human HeLa P4/R5 cells assessed as i... 19596885
Human immunodeficiency virus 1 EC50 = 270.0 nM 6.57 Antiviral activity against wild type HIV1 NL4-3 produced from full length pR9del... 17967913

Literature References

PubMed DOI Target Context # Activities
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 62
19104010 10.1128/aac.00984-08 Human immunodeficiency virus 1 23
18676881 10.1128/aac.00654-08 Woodchuck hepatitis virus 22
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18676881 10.1128/aac.00654-08 Marmota monax 9
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37393791 10.1016/j.ejmech.2023.115586 Human immunodeficiency virus 1 4
19223644 10.1128/aac.01593-08 Human immunodeficiency virus 1 4
34795872 10.1021/acsmedchemlett.1c00428 Unchecked 4
28351588 10.1016/j.bmcl.2017.03.031 Unchecked 3
17967913 10.1128/aac.01004-07 Human immunodeficiency virus 1 3
19596885 10.1128/aac.00392-09 Human immunodeficiency virus 1 3
34795872 10.1021/acsmedchemlett.1c00428 Human immunodeficiency virus 1 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
32515595 10.1021/acs.jmedchem.0c00358 Human immunodeficiency virus 1 3
37393791 10.1016/j.ejmech.2023.115586 ADMET 3
37393791 10.1016/j.ejmech.2023.115586 Unchecked 3
17172311 10.1124/dmd.106.012765 Multidrug resistance-associated protein 1 2
22352809 10.1021/jm201551m Human immunodeficiency virus 1 2

Data from ChEMBL 36 via Core Engine