EMTRICITABINE

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Trade Names
Synonyms
FTC
Status
Molecule Category Free-form
ATC J05AF09
UNII ULS8902U4O
EPA CompTox DTXSID0040129

Structure

InChI Key XQSPYNMVSIKCOC-NTSWFWBYSA-N
Smiles Nc1nc(=O)n([C@@H]2CS[C@H](CO)O2)cc1F
InChI
InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H10FN3O3S
Molecular Weight 247.25
AlogP -0.46
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 90.37
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 16.0

Bioactivity

Mechanism of Action Action Reference
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Secreted protein
- - 44000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 17
Assay Description Organism Bioactivity Reference
Inhibition of hepatitis B virus replication in the HepAD38 cell line. Homo sapiens 30.0 nM
Anti-HIV-1 activity against human peripheral blood mononuclear (PBM) cells infected with HIV-1 strain LAV Human immunodeficiency virus 1.3 nM
Antiviral activity against HBV in HepG2.2.15 cells assessed as decrease in extracellular viral DNA level by RT-PCR Hepatitis B virus 100.0 nM
Antiviral activity against wild type HIV1 NL4-3 produced from full length pR9deltaApa infected in human MAGIC-5A cells assessed as inhibition of Lac+ foci expression after 40 hrs Human immunodeficiency virus 1 270.0 nM
Antiviral activity against wild type HIV2 ROD produced from full length pROD9 infected in human MAGIC-5A cells assessed as inhibition of Lac+ foci expression after 40 hrs Human immunodeficiency virus type 2 (ISOLATE ROD) 500.0 nM
Antiviral activity against multinucleoside-resistant HIV1 NL4-3 harboring A62V, V75I, F77L, F116Y, Q151M mutation in viral reverse transcriptase infected in human MAGIC-5A cells assessed as inhibition of Lac+ foci expression after 40 hrs Human immunodeficiency virus 1 790.0 nM
Antiviral activity against HIV1 3B infected in human MT-2 cells by two fold dilution method in presence of 10% FBS Human immunodeficiency virus 1 323.0 nM
Antiviral activity against HIV1 isolate 056 expressing wild type reverse transcriptase gene by phenosense assay Human immunodeficiency virus 1 890.0 nM
Antiviral activity against HIV1 infected in human HeLa P4/R5 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 170.0 nM
Antiviral activity against HIV1 infected in human MT2 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 44.0 nM
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication Human immunodeficiency virus 1 1.0 nM
Antiviral activity against HIV1 BaL infected in HeLa P4/R5 cells assessed as reduction of viral infection incubated for 2 hrs followed by incubated in drug-free medium for 46 hrs by single round infection beta-galactosidase reporter gene assay Human immunodeficiency virus 1 800.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 6.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 17.1 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 20.7 %
Antiviral activity against subtype B X4 tropic HIV1 3B infected in GFP-positive human CEM cells expressing CD4+,CXCR4 and CCR5 after 3 days Human immunodeficiency virus 1 40.0 nM
Inhibition of HIV1 BaL dinucleoside reverse transcriptase infected in human P4R5 MAGI cells assessed as reduction in viral infection after 2 hrs by Galacto-Star beta-galactosidase reporter gene assay Human immunodeficiency virus 1 700.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -3.69 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.5 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -6.58 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.11 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.11 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 %
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus 1 10.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus type 1 16.0 nM
Antiviral activity against HIV2 ROD infected in human TK-deficient CEM/TK(-) cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus type 1 46.0 nM
Antiviral activity against wild type HIV1 NL4-3 infected in human CEM-GXR cells assessed as inhibition of viral replication measured after 3 days by Flowcytometry assay Human immunodeficiency virus 1 30.0 nM
Antiviral activity against wild type HIV1 97USSN54 infected in human CEM-GXR cells assessed as inhibition of viral replication measured after 3 days by Flowcytometry assay Human immunodeficiency virus 1 30.0 nM
Anti-HIV activity against HIV1 Bal infected in human PBMC assessed as inhibition of viral infection measured after 11 days by ELISA method Human immunodeficiency virus 1 2.1 nM
Anti-HIV activity against HIV1 3B infected in human PBMC assessed as inhibition of viral infection measured after 11 days by ELISA method Human immunodeficiency virus 5.5 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Germany

Cross References

Resources Reference
ChEBI 31536
ChEMBL CHEMBL885
DrugBank DB00879
DrugCentral 1003
FDA SRS ULS8902U4O
Human Metabolome Database HMDB0015017
Guide to Pharmacology 11244
KEGG C12599
PDB ETV
PharmGKB PA10069
PubChem 60877
SureChEMBL SCHEMBL39708
ZINC ZINC000003629271
CONTENTS