Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H16Cl2N2O2 |
| Molecular Weight | 351.227 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C2=C(Cl)C=CC=C2Cl
InChI
InChIKey=CJPLEFFCVDQQFZ-UHFFFAOYSA-N
InChI=1S/C17H16Cl2N2O2/c1-9-6-7-11(10(2)22)14(8-9)21-16(17(20)23)15-12(18)4-3-5-13(15)19/h3-8,16,21H,1-2H3,(H2,20,23)
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Potent and highly selective human immunodeficiency virus type 1 (HIV-1) inhibition by a series of alpha-anilinophenylacetamide derivatives targeted at HIV-1 reverse transcriptase. | 1993 Mar 1 |
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| Thiadiazole derivatives: highly potent and specific HIV-1 reverse transcriptase inhibitors. | 1995 Jun 9 |
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| Potent and specific inhibition of human immunodeficiency virus type 1 replication by 4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-Y1 N,N-dialkylcarbamate derivatives. | 1995 Oct |
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| Anti-HIV and anti-HBV activity and resistance profile of 2',3'-dideoxy-3'-thiacytidine (3TC) and its arylphosphoramidate derivative CF 1109. | 1996 Aug 14 |
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| Complete inhibition of viral breakthrough by combination of MKC-442 with AZT during a long-term culture of HIV-1 infected cells. | 1996 Jun |
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| Antiviral activity of the bicyclam derivative JM3100 against drug-resistant strains of human immunodeficiency virus type 1. | 1996 Mar |
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| Inhibitory effect of 4-(2, 6-dichlorophenyl)-1, 2, 5-thiadiazol-3-yl-N-methyl, N-ethylcarbamate on replication of human immunodeficiency virus type 1 and the mechanism of action. | 1996 May |
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| Thiadiazole derivatives: highly potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) replications in vitro. | 1997 |
|
| Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. | 1997 Apr |
|
| 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 |
|
| 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 |
|
| 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 |
|
| S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1. | 1998 Jun |
|
| 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 |
|
| Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. | 1999 Aug |
|
| Activity of non-nucleoside reverse transcriptase inhibitors against HIV-2 and SIV. | 1999 Aug 20 |
|
| Inhibition of human immunodeficiency virus replication by RD6-Y664, a novel benzylhydroxylamine derivative. | 1999 Mar |
|
| Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217. | 1999 Nov |
|
| Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients. | 2000 Jun 10 |
|
| The Lys103Asn mutation of HIV-1 RT: a novel mechanism of drug resistance. | 2001 Jun 1 |
|
| Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU). | 2001 Sep 3 |
|
| Observations of HIV-1 genotypic drug resistance in a trial of four reverse transcriptase inhibitors (Quattro Trial). | 2002 Mar |
|
| N-aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action. | 2003 Apr 10 |
|
| Commentary on using the SF-36 or MOS-HIV in studies of persons with HIV disease. | 2003 Jul 9 |
|
| Validation of a general measure of treatment satisfaction, the Treatment Satisfaction Questionnaire for Medication (TSQM), using a national panel study of chronic disease. | 2004 Feb 26 |
|
| Characteristics and management of HIV-1-infected pregnant women enrolled in a randomised trial: differences between Europe and the USA. | 2007 Jun 20 |
|
| Characterization of physico-chemical properties and pharmaceutical performance of sucrose co-freeze-dried solid nanoparticulate powders of the anti-HIV agent loviride prepared by media milling. | 2007 Jun 29 |
|
| Drying of crystalline drug nanosuspensions-the importance of surface hydrophobicity on dissolution behavior upon redispersion. | 2008 Sep 2 |
|
| Validation of an abbreviated Treatment Satisfaction Questionnaire for Medication (TSQM-9) among patients on antihypertensive medications. | 2009 Apr 27 |
|
| Rapid and persistent selection of the K103N mutation as a majority quasispecies in a HIV1-patient exposed to efavirenz for three weeks: a case report and review of the literature. | 2009 Sep 18 |
|
| Development of a liposomal nanodelivery system for nevirapine. | 2010 Jul 13 |
|
| Drug supersaturation in simulated and human intestinal fluids representing different nutritional states. | 2010 Nov |
Sample Use Guides
Through optimization of a lead compound, several alpha-anilinophenylacetamide (alpha-APA) derivatives have been identified that inhibit the replication of several HIV-1 strains (IIIB/LAI, RF, NDK, MN, HE) in a variety of host cell types at concentrations that are 10,000- to 100,000-fold lower than their cytotoxic concentrations. The IC50 of the alpha-APA derivative R 89439 for HIV-1 cytopathicity in MT-4 cells was 13 nM. The median 90% inhibitory concentration (IC90) in a variety of host cells was 50-100 nM.
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C166692
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100000082246
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7196
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3S1R1LZ09H
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SUB08605MIG
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147362-57-0
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JJ-14
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3963
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CHEMBL37624
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LOVIRIDE
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DTXSID60869958
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ACTIVE MOIETY
