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
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
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Bifunctional inhibition of HIV-1 reverse transcriptase: a first step in designing a bifunctional triphosphate. | 2013-03-01 |
|
| 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. | 2005-11-17 |
|
| 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. | 2001-02-01 |
|
| Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents. | 2000-03 |
|
| 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. | 1999-11 |
|
| Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNIs). | 1999-11 |
|
| Inhibition of human immunodeficiency virus type (HIV-1) replication by some diversely functionalized spirocyclopropyl derivatives. | 1999-05 |
|
| Prediction of binding affinities for TIBO inhibitors of HIV-1 reverse transcriptase using Monte Carlo simulations in a linear response method. | 1998-12-17 |
|
| 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. | 1998-12 |
|
| Synthesis, structure and in vitro anti-human immunodeficiency virus activity of novel 3-methyl-1H,3H-thiazolo[3,4-a]benzimidazoles. | 1998-09 |
|
| Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent. | 1998-07-09 |
|
| 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. | 1998-03 |
|
| 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. | 1998-02-10 |
|
| 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. | 1997-11 |
|
| Development of resistance of human immunodeficiency virus type 1 to dextran sulfate associated with the emergence of specific mutations in the envelope gp120 glycoprotein. | 1997-07 |
|
| Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo-[4,5,1-jk][1,4]benzodiazepin- 2(1H)-one (TlBO) derivatives. 4. | 1995-03-03 |
|
| Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo [4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives. 3. | 1995-03-03 |
|
| New tetrahydroimidazo[4,5,1-jk][1,4]-benzodiazepin-2(1H)-one and -thione derivatives are potent inhibitors of human immunodeficiency virus type 1 replication and are synergistic with 2',3'-dideoxynucleoside analogs. | 1994-12 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:06:45 GMT 2025
by
admin
on
Mon Mar 31 18:06:45 GMT 2025
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| Record UNII |
7WP69N3Y3Y
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| Record Status |
Validated (UNII)
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C97453
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C76930
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DB08600
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