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

Molecular Formula	C15H20N2O3S2
Molecular Weight	340.461
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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
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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:06:14 GMT 2023` Edited by `admin` on `Fri Dec 15 16:06:14 GMT 2023`
Record UNII	XZ4KT6MO4X
Record Status	`Validated (UNII)`
Record Version

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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