ETRAVIRINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2008)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J05AG04
UNII: 0C50HW4FO1

Structure
InChI Key PYGWGZALEOIKDF-UHFFFAOYSA-N
Smile Cc1cc(C#N)cc(C)c1Oc1nc(Nc2ccc(C#N)cc2)nc(N)c1Br
InChI
InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H15BrN6O
Molecular Weight 435.29
AlogP 4.72
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 120.64
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Slow voltage-gated potassium channel accessory protein family
- 1258925.41 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 7480-7480 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 496-500 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 277-280 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 12000-12020 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 41300-41340 - - -
Enzyme Hydrolase
2-46 0.6-6500 1460 - 32.7-56.4
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 4000 - - -
Enzyme Transferase
- - - - -4.461-14.6
Enzyme
2-46 0.6-6500 1460 - 32.7-56.4
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -9.58--0.67
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 25118.86-398107.17 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 501187.23-3981071.71 - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 7600 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 5100 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 6000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV 4 D006678 FDA
HIV Infections 4 D015658 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Friedreich Ataxia 2 D005621 ClinicalTrials
Infections 1 D007239 ClinicalTrials

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
10.23
General disorders and administration site conditions
9.04
Gastrointestinal disorders
7.76
Nervous system disorders
7.49
Skin and subcutaneous tissue disorders
5.11
Pregnancy, puerperium and perinatal conditions
5.02
Investigations
4.93
Infections and infestations
4.52
Metabolism and nutrition disorders
4.38
Respiratory, thoracic and mediastinal disorders
4.25
Congenital, familial and genetic disorders
4.11
Musculoskeletal and connective tissue disorders
3.88
Product issues
3.65
Hepatobiliary disorders
3.47
Vascular disorders
3.47
Cardiac disorders
3.2
Psychiatric disorders
3.15
Renal and urinary disorders
3.06
Blood and lymphatic system disorders
2.1

Cross References

Resources Reference
CAS NUMBER 269055-15-4
ChEBI 63589
ChEMBL CHEMBL308954
DrugBank DB06414
DrugCentral 1115
EPA CompTox DTXSID30181412
FDA SRS 0C50HW4FO1
KEGG D04112
PDB 65B
PharmGKB PA166014703
PubChem 193962
SureChEMBL SCHEMBL52691
ZINC ZINC000000602632
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