EMTRICITABINE

Search structure
Trade Names:
Synonyms:
FTC
Status: Approved (2003)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: J05AF09
UNII: ULS8902U4O

Structure
InChI Key XQSPYNMVSIKCOC-NTSWFWBYSA-N
Smile 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

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase 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

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Infections 3 D007239 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Hepatitis B, Chronic 3 D019694 ClinicalTrials
Hepatitis B, Chronic 3 D019694 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Liver Cirrhosis, Biliary 2 D008105 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Insulin Resistance 1 D007333 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Infection 44.0
Skin and subcutaneous tissue disorders Skin hyperpigmentation 32.0
Skin and subcutaneous tissue disorders Skin discolouration 31.8
Respiratory, thoracic and mediastinal disorders Cough 28.0
Social circumstances Fasting 24.0
Ear and labyrinth disorders Otitis media 23.0
Gastrointestinal disorders Vomiting 23.0
Skin and subcutaneous tissue disorders Dermatitis 21.0
Skin and subcutaneous tissue disorders Rash 21.0
Gastrointestinal disorders Diarrhoea 20.0
Infections and infestations Rhinitis 20.0
Investigations Body temperature increased 18.0
Infections and infestations Pneumonia 15.0
Gastrointestinal disorders Diarrhoea 14.0
Gastrointestinal disorders Gastroenteritis 11.0
Nervous system disorders Headache 10.2
Gastrointestinal disorders Abdominal pain 10.0
Gastrointestinal disorders Gastrointestinal pain 10.0
Gastrointestinal disorders Nausea 10.0
Blood and lymphatic system disorders Anaemia 9.5
Skin and subcutaneous tissue disorders Dermatitis 9.0
Skin and subcutaneous tissue disorders Rash 9.0
General disorders and administration site conditions Asthenia 8.0
General disorders and administration site conditions Fatigue 8.0
Blood and lymphatic system disorders Anaemia 7.0
Psychiatric disorders Depression 7.0
Cardiac disorders Dizziness 7.0
Nervous system disorders Insomnia 7.0
Gastrointestinal disorders Nausea 7.0
Gastrointestinal disorders Diarrhoea 5.0
Nervous system disorders Headache 5.0
Infections and infestations Upper respiratory tract infection 5.0
Gastrointestinal disorders Vomiting 5.0
Infections and infestations Sinusitis 4.0
Renal and urinary disorders Haematuria 3.0
Infections and infestations Nasopharyngitis 3.0
Social circumstances Fasting 2.0
Renal and urinary disorders Haematuria 2.0
Endocrine disorders Hyperglycaemia 2.0
Renal and urinary disorders Glycosuria 1.0
Endocrine disorders Hyperglycaemia 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
13.56
General disorders and administration site conditions
11.58
Pregnancy, puerperium and perinatal conditions
10.59
Congenital, familial and genetic disorders
9.32
Renal and urinary disorders
6.78
Nervous system disorders
6.36
Immune system disorders
6.07
Infections and infestations
5.79
Investigations
5.79
Musculoskeletal and connective tissue disorders
3.11
Metabolism and nutrition disorders
2.97
Skin and subcutaneous tissue disorders
2.97

Cross References

Resources Reference
CAS NUMBER 143491-57-0
ChEBI 31536
ChEMBL CHEMBL885
DrugBank DB00879
DrugCentral 1003
EPA CompTox DTXSID0040129
FDA SRS ULS8902U4O
Human Metabolome Database HMDB0015017
Guide to Pharmacology 11244
KEGG C12599
PDB ETV
PharmGKB PA10069
PubChem 60877
SureChEMBL SCHEMBL39708
ZINC ZINC000003629271
CONTENTS