Tivirapine
Basic information
- CAS
137332-54-8- Standard SMILES
CC(C)=CCN1Cc2c(Cl)ccc3[nH]c(=S)n(c23)C[C@@H]1C- InChIKey
ZNFFMCYSMBXZQU-NSHDSACASA-N- Molecular formula
- C16H20ClN3S
- Average molar mass
- 321.9 g/mol
- Monoisotopic mass
- 321.1066465
Overview
Tivirapine is a benzodiazepine non-nucleoside reverse transcriptase inhibitor with activity against human immunodeficiency viruses 1 and 2 and simian immunodeficiency virus. Tivirapine inhibits replication in both wild-type and drug-resistant HIV-1 isolates.
Names & identifiers
- Preferred name
- Tivirapine
- IUPAC
- (11S)-7-chloro-11-methyl-10-(3-methylbut-2-enyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-4(13),5,7-triene-2-thione
- English name
- 4,5,6,7-Tetrahydro-5α-methyl-6-(3-methyl-2-butenyl)-8-chloroimidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione
- Molecular formula
- C16H20ClN3S
- Molecular weight
- 321.87
Names & synonyms
Tivirapine137332-54-8Tivirapine [INN]UNII-7WP69N3Y3Y7WP69N3Y3Y8-Cl-TIBONSC 636661NSC-636661CHEMBL58711NSC636661(11S)-7-chloro-11-methyl-10-(3-methylbut-2-enyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-4(13),5,7-triene-2-thioneR-87027
Show more names
R-86183Aids002738Aids-0027388-Chloro-TIBO4,5,6,7-Tetrahydro-5α-methyl-6-(3-methyl-2-butenyl)-8-chloroimidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione(5S)-6-(3-Methyl-2-butenyl)-4,5,6,7-tetrahydro-5α-methyl-8-chloroimidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione(+)-(S)-4,5,6,7-Tetrahydro-8-chloro-5-methyl-6-(3-methyl-2-butenyl)imidazo[4,5,1-jk][1,4]benzodiazepine-2-(1H)-thione
5-CHLORO-8-METHYL-7-(3-METHYL-BUT-2-ENYL)-6,7,8,9-TETRAHYDRO-2H-2,7,9A-TRIAZA-BENZO[CD]AZULENE-1-THIONE(5S)-8-chloro-5-methyl-6-(3-methylbut-2-en-1-yl)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione(S)-8-Chloro-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)imidazo(4,5,1-jk)(1,4)benzodiazepine-2(1H)-thionetivirapinaTivirapin1uwbR 86183; TIBO-R 861838-ClTIBO
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 50.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 449
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 441.864 · 441.864±55.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.308 · 1.308±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 9.372 · 9.372±0.40(predicted)
- FDA UNII
- 7 WP69N3Y3Y · 7WP69N3Y3Y
Chemistry & industry
Applications
UsesTivirapine (R86183) is a nonnucleoside HIV-1 RT inhibitor against HIV-1-induced cytopathic effects with an EC50 value of 4 nM. Tivirapine inhibits the Yl8lC mutant of HIV-1 RT[1].
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Compound notes
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