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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20ClN3S
Molecular Weight 321.868
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIVIRAPINE

SMILES

C[C@H]1CN2C(=S)NC3=C2C(CN1CC=C(C)C)=C(Cl)C=C3

InChI

InChIKey=ZNFFMCYSMBXZQU-NSHDSACASA-N
InChI=1S/C16H20ClN3S/c1-10(2)6-7-19-9-12-13(17)4-5-14-15(12)20(8-11(19)3)16(21)18-14/h4-6,11H,7-9H2,1-3H3,(H,18,21)/t11-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H20ClN3S
Molecular Weight 321.868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Tivirapine, also known as R-86183, is a HIV-1 specific reverse transcriptase inhibitor. It inhibits the replication of HIV-1, but not HIV-2, in a variety of CD4+ T-cell lines and peripheral blood lymphocytes. Whereas an HIV-1 strain containing the Leu-100-->Ile mutation in the RT gene is about 400-fold less susceptible, R86183 still inhibits the replication of an HIV-1 strain containing the Tyr-181-->Cys RT mutation by 50% at a concentration of 130 nM. Tivirapine had been in phase I clinical trial for the treatment of HIV-1 infection. However, this development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:06:45 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:45 GMT 2025
Record UNII
7WP69N3Y3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-636661
Preferred Name English
TIVIRAPINE
INN  
INN  
Official Name English
tivirapine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97453
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
Code System Code Type Description
PUBCHEM
3000323
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
FDA UNII
7WP69N3Y3Y
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
NCI_THESAURUS
C76930
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL306904
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
DRUG BANK
DB08600
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID00160138
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
SMS_ID
100000082140
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
INN
7421
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
EVMPD
SUB11124MIG
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
NSC
636661
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
CAS
137332-54-8
Created by admin on Mon Mar 31 18:06:45 GMT 2025 , Edited by admin on Mon Mar 31 18:06:45 GMT 2025
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY