LOVIRIDE

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

Structure Search

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)

HIDE SMILES / InChI

Molecular Formula	C17H16Cl2N2O2
Molecular Weight	351.227
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7680476 | https://adisinsight.springer.com/drugs/800002631 | https://www.ncbi.nlm.nih.gov/pubmed/9164314

Loviride (R 89439) is a non-nucleoside inhibitor of reverse transcriptase. It inhibits virion and recombinant reverse transcriptase of HIV-1. It was being studied in the combination therapy of HIV infection with other anti-HIV agents.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus 1 33 Target ID: CHEMBL378 Sources: https://adisinsight.springer.com/drugs/800002631\|https://www.ncbi.nlm.nih.gov/pubmed/22268494	Inhibitor 8297		14.0 nM [IC50]
Human immunodeficiency virus type 1 protease 35 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11371163\|https://www.ncbi.nlm.nih.gov/pubmed/9835502	Inhibitor 8297		500.0 nM [IC50]

PubMed

Title	Date	PubMed
Thiadiazole derivatives: highly potent and specific HIV-1 reverse transcriptase inhibitors.	1995 Jun 9	7540208
Antiviral activity of the bicyclam derivative JM3100 against drug-resistant strains of human immunodeficiency virus type 1.	1996 Mar	8739608
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	8799326
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
S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1.	1998 Jun	9624472
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	10875608
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	17363200
Drying of crystalline drug nanosuspensions-the importance of surface hydrophobicity on dissolution behavior upon redispersion.	2008 Sep 2	18644441
Validation of an abbreviated Treatment Satisfaction Questionnaire for Medication (TSQM-9) among patients on antihypertensive medications.	2009 Apr 27	19397800
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	21092074

Sample Use Guides

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:59:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:19 GMT 2023`
Record UNII	3S1R1LZ09H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOVIRIDE

Official Name

English

LOVIRIDE [USAN]

Common Name

English

(±)-2-(6-ACETYL-M-TOLUIDINO)-2-(2,6-DICHLOROPHENYL)ACETAMIDE

Systematic Name

English

loviride [INN]

Common Name

English

Loviride [WHO-DD]

Common Name

English

R-89439

Code

English

LOVIRIDE [MART.]

Common Name

English

BENZENEACETAMIDE, .ALPHA.-((2-ACETYL-5-METHYLPHENYL)AMINO)-2,6-DICHLORO-, (±)-

Systematic Name

English

Code System Code Type Description

NCI_THESAURUS

C166692