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

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
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	8753770
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide.	1999 Aug	10428899
Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217.	1999 Nov	10628806
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).	2001 Sep 3	11527703
N-aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action.	2003 Apr 10	12672256
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	14987333
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

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.

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