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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 of LOVIRIDE

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 14.0 nM [IC50]
Inhibitor
8297
 500.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
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
Thiadiazole derivatives: highly potent and specific HIV-1 reverse transcriptase inhibitors.
1995 Jun 9
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
Thiadiazole derivatives: highly potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) replications in vitro.
1997
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
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

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 UTC 2023
Edited
by admin
on Fri Dec 15 15:59:19 UTC 2023
Record UNII
3S1R1LZ09H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOVIRIDE
INN   MART.   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
SMS_ID
100000082246
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
INN
7196
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
FDA UNII
3S1R1LZ09H
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
EVMPD
SUB08605MIG
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
CAS
147362-57-0
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
USAN
JJ-14
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
PUBCHEM
3963
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL37624
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
WIKIPEDIA
LOVIRIDE
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID60869958
Created by admin on Fri Dec 15 15:59:19 UTC 2023 , Edited by admin on Fri Dec 15 15:59:19 UTC 2023
PRIMARY
Related Record Type Details
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of LOVIRIDE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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