TIVIRAPINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7535037 | https://www.ncbi.nlm.nih.gov/pubmed/10321027 | https://www.ncbi.nlm.nih.gov/pubmed/7542558 | https://adisinsight.springer.com/drugs/800002747

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
Development of resistance of human immunodeficiency virus type 1 to dextran sulfate associated with the emergence of specific mutations in the envelope gp120 glycoprotein.	1997 Jul	9224818
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
Prediction of binding affinities for TIBO inhibitors of HIV-1 reverse transcriptase using Monte Carlo simulations in a linear response method.	1998 Dec 17	9857095
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
1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine (TTD) derivatives: a new class of nonnucleoside human immunodeficiency virus type 1 (HIV-1) reverse transcriptase inhibitors with anti-HIV-1 activity.	1998 Mar	9517942
Synthesis, structure and in vitro anti-human immunodeficiency virus activity of novel 3-methyl-1H,3H-thiazolo[3,4-a]benzimidazoles.	1998 Sep	9875396
Inhibition of human immunodeficiency virus type (HIV-1) replication by some diversely functionalized spirocyclopropyl derivatives.	1999 May	10366901
Synthesis and anti-HIV activity of 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (TBO) derivatives. Truncated 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2( 1H)-on es (TIBO) analogues.	1999 Nov	10632052
Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNIs).	1999 Nov	10632038
Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents.	2000 Mar	10819438
Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent.	2001 Feb 1	11462972
Specific targeting highly conserved residues in the HIV-1 reverse transcriptase primer grip region. Design, synthesis, and biological evaluation of novel, potent, and broad spectrum NNRTIs with antiviral activity.	2005 Nov 17	16279773
Bifunctional inhibition of HIV-1 reverse transcriptase: a first step in designing a bifunctional triphosphate.	2013 Mar 1	23380374

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:26 UTC 2023` Edited by `admin` on `Fri Dec 15 15:43:26 UTC 2023`
Record UNII	7WP69N3Y3Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIVIRAPINE

Official Name

English

tivirapine [INN]

Common Name

English

NSC-636661

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C97453