TALVIRALINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H20N2O3S2
Molecular Weight	340.461
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(NC(=S)[C@H](CSC)N2C(=O)OC(C)C)C=C1

InChI

InChIKey=GWKIPRVERALPRD-ZDUSSCGKSA-N

InChI=1S/C15H20N2O3S2/c1-9(2)20-15(18)17-12-7-10(19-3)5-6-11(12)16-14(21)13(17)8-22-4/h5-7,9,13H,8H2,1-4H3,(H,16,21)/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8619578 | https://www.ncbi.nlm.nih.gov/pubmed/9952383

Talviraline (HBY 097) was developed as a nonnucleoside inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (NNRTI) for the treatment of HIV Infections. Talviraline participated in a phase II clinical trial. It was found that the drug caused pronounced acute suppression of HIV-1 replication both in combination with zidovudine and alone. However, further development of the drug has been discontinued.

Approval Year

PubMed

Title	Date	PubMed
Preclinical evaluation of HBY 097, a new nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 replication.	1995 Oct	8619578
Selective pressure of a quinoxaline nonnucleoside inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) on HIV-1 replication results in the emergence of nucleoside RT-inhibitor-specific (RT Leu-74-->Val or Ile and Val-75-->Leu or Ile) HIV-1 mutants.	1996 Jan 9	8552634
In vitro selection for different mutational patterns in the HIV-1 reverse transcriptase using high and low selective pressure of the nonnucleoside reverse transcriptase inhibitor HBY 097.	1997 Apr 28	9143309
Zidovudine-resistant human immunodeficiency virus type 1 strains subcultured in the presence of both lamivudine and quinoxaline HBY 097 retain marked sensitivity to HBY 097 but not to lamivudine.	1997 Nov	9359746
Characteristics of the Pro225His mutation in human immunodeficiency virus type 1 (HIV-1) reverse transcriptase that appears under selective pressure of dose-escalating quinoxaline treatment of HIV-1.	1997 Nov	9343170
Patterns of resistance and cross-resistance to human immunodeficiency virus type 1 reverse transcriptase inhibitors in patients treated with the nonnucleoside reverse transcriptase inhibitor loviride.	1998 Dec	9835502
A novel mutation (F227L) arises in the reverse transcriptase of human immunodeficiency virus type 1 on dose-escalating treatment of HIV type 1-infected cell cultures with the nonnucleoside reverse transcriptase inhibitor thiocarboxanilide UC-781.	1998 Feb 10	9491916
Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent.	1998 Jul 9	9677161
A proline-to-histidine substitution at position 225 of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) sensitizes HIV-1 RT to BHAP U-90152.	1998 Jun	9634074
Retention of marked sensitivity to (S)-4-isopropoxycarbonyl-6-methoxy-3-(methylthiomethyl)-3,4-di hydroquin oxaline-2(1H)-thione (HBY 097) by an azidothymidine (AZT)-resistant human immunodeficiency virus type 1 (HIV-1) strain subcultured in the combined presence of quinoxaline HBY 097 and 2',3'-dideoxy-3'-thiacytidine (lamivudine).	1998 Mar 1	9515572
Structures of Tyr188Leu mutant and wild-type HIV-1 reverse transcriptase complexed with the non-nucleoside inhibitor HBY 097: inhibitor flexibility is a useful design feature for reducing drug resistance.	1998 Nov 27	9813120
Urea-PETT compounds as a new class of HIV-1 reverse transcriptase inhibitors. 3. Synthesis and further structure-activity relationship studies of PETT analogues.	1999 Oct 7	10514285
Mutational analysis of trp-229 of human immunodeficiency virus type 1 reverse transcriptase (RT) identifies this amino acid residue as a prime target for the rational design of new non-nucleoside RT inhibitors.	2000 May	10779379

Sample Use Guides

In Vivo Use Guide

HBY 097 (TALVIRALINE) monotherapy (250 mg three times daily)

Route of Administration: Oral

Name

Type

Language

TALVIRALINE

Official Name

English

Talviraline [WHO-DD]

Common Name

English

TALVIRALINE [MART.]

Common Name

English

1(2H)-QUINOXALINECARBOXYLIC ACID, 3,4-DIHYDRO-7-METHOXY-2-((METHYLTHIO)METHYL)-3-THIOXO-, 1-METHYLETHYL ESTER, (2S)-

Systematic Name

English

HBY-097

Code

English

3,4-DIHYDRO-7-METHOXY-2-((METHYLTHIO)-METHYL)-3-THIOXO-1(2H)-QUINOXALINECARBOXYLIC ACID 1-METHYLETHYL ESTER, S-

Systematic Name

English

ISOPROPYL (2S)-3,4-DIHYDRO-7-METHOXY-2-((METHYLTHIO)METHYL)-3-THIOXO-1(2H)-QUINOXALINECARBOXYLATE

Systematic Name

English

HBY097

Code

English

talviraline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453