Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H18ClNO2S |
| Molecular Weight | 335.848 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCOC1=C(Cl)C=CC(NC(=S)C2=C(C)OC=C2)=C1
InChI
InChIKey=YZHIXLCGPOTQNB-UHFFFAOYSA-N
InChI=1S/C17H18ClNO2S/c1-11(2)6-8-21-16-10-13(4-5-15(16)18)19-17(22)14-7-9-20-12(14)3/h4-7,9-10H,8H2,1-3H3,(H,19,22)
| Molecular Formula | C17H18ClNO2S |
| Molecular Weight | 335.848 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
N-(4-Chloro-3-((3-Methyl-2-Butenyl)Oxy)Phenyl)-2-Methyl-3-Furancarbothioamide (also known as UC-781) is a thiocarboxanilide non-nucleoside reverse transcriptase inhibitor patented by Uniroyal Chemical Company, Inc. for prevention of HIV transmission. UC-781 is a potent inhibitor of reverse transcriptase-dependent pyrophosphorolysis, and purportedly restores the chain-terminating activity of zidovudine (AZT) against AZT-resistant virus. In clinical trials single and 7-day topical rectal exposure of UC-781 was safe with no significant adverse events, no detected UC-781 plasma drug levels, no significant mucosal changes, and high participant acceptability. Ex vivo biopsy infections demonstrated marked suppression of HIV infectibility, identifying a potential early biomarker of efficacy.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. | 1997 Apr |
|
| Chemical barriers to human immunodeficiency virus type 1 (HIV-1) infection: retrovirucidal activity of UC781, a thiocarboxanilide nonnucleoside inhibitor of HIV-1 reverse transcriptase. | 1997 Apr |
|
| Efficacy, pharmacokinetics, and in vivo antiviral activity of UC781, a highly potent, orally bioavailable nonnucleoside reverse transcriptase inhibitor of HIV type 1. | 1997 Jun 10 |
|
| Models which explain the inhibition of reverse transcriptase by HIV-1-specific (thio)carboxanilide derivatives. | 1997 May 19 |
|
| 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 |
|
| Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent. | 1998 Jul 9 |
|
| Crystal structures of HIV-1 reverse transcriptase in complex with carboxanilide derivatives. | 1998 Oct 13 |
|
| Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors. | 2000 Apr 10 |
|
| Human immunodeficiency virus type 1 reverse transcriptase dimer destabilization by 1-[Spiro[4"-amino-2",2" -dioxo-1",2" -oxathiole-5",3'-[2', 5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]]]-3-ethylthy mine. | 2000 Feb 15 |
|
| Inhibition of human immunodeficiency virus by a new class of pyridine oxide derivatives. | 2003 Sep |
|
| In vitro comparison of topical microbicides for prevention of human immunodeficiency virus type 1 transmission. | 2004 Oct |
|
| A series of diaryltriazines and diarylpyrimidines are highly potent nonnucleoside reverse transcriptase inhibitors with possible applications as microbicides. | 2004 Oct |
|
| The N137 and P140 amino acids in the p51 and the P95 amino acid in the p66 subunit of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase are instrumental to maintain catalytic activity and to design new classes of anti-HIV-1 drugs. | 2005 Apr 25 |
|
| Combination of candidate microbicides cellulose acetate 1,2-benzenedicarboxylate and UC781 has synergistic and complementary effects against human immunodeficiency virus type 1 infection. | 2005 May |
|
| Marked depletion of glycosylation sites in HIV-1 gp120 under selection pressure by the mannose-specific plant lectins of Hippeastrum hybrid and Galanthus nivalis. | 2005 May |
|
| Characterization of cyclodextrin inclusion complexes of the anti-HIV non-nucleoside reverse transcriptase inhibitor UC781. | 2008 Dec |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:37:10 GMT 2023
by
admin
on
Fri Dec 15 16:37:10 GMT 2023
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| Record UNII |
L7K247H29H
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97453
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178870-32-1
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L7K247H29H
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DTXSID10170581
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3000926
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C78046
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DB05871
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