U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17FN2O3
Molecular Weight 280.2948
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OPAVIRALINE

SMILES

CC[C@@H]1N(C(=O)OC(C)C)C2=C(NC1=O)C=CC(F)=C2

InChI

InChIKey=KELNNWMENBUHNS-NSHDSACASA-N
InChI=1S/C14H17FN2O3/c1-4-11-13(18)16-10-6-5-9(15)7-12(10)17(11)14(19)20-8(2)3/h5-8,11H,4H2,1-3H3,(H,16,18)/t11-/m0/s1

HIDE SMILES / InChI
Opaviraline (also known as GW 420867), a nonnucleoside reverse transcriptase inhibitor that was studied for the treatment of HIV infections. The drug participated in clinical trials phase II in Germany, in South Africa, and in the United Kingdom, however, these studies were discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Mutational analysis of trp-229 of human immunodeficiency virus type 1 reverse transcriptase (RT) identifies this amino acid residue as a prime target for the rational design of new non-nucleoside RT inhibitors.
2000 May
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
Discovery of TSAO derivatives with an unusual HIV-1 activity/resistance profile.
2006 Aug
Name Type Language
OPAVIRALINE
INN  
INN  
Official Name English
HBY-1293
Code English
GW-420867
Code English
opaviraline [INN]
Common Name English
ISOPROPYL (S)-2-ETHYL-7-FLUORO-3,4-DIHYDRO-3-OXO-1(2H)-QUINOXALINECARBOXYLATE
Systematic Name English
GW-420867X
Code English
Classification Tree Code System Code
NCI_THESAURUS C97453
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
Code System Code Type Description
DRUG BANK
DB07884
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
PRIMARY
FDA UNII
Q3A8EU2NMU
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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NCI_THESAURUS
C90786
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
PRIMARY
PUBCHEM
154048
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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SMS_ID
300000034254
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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ChEMBL
CHEMBL301370
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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CAS
178040-94-3
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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EPA CompTox
DTXSID60170415
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
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INN
8020
Created by admin on Fri Dec 15 16:30:38 GMT 2023 , Edited by admin on Fri Dec 15 16:30:38 GMT 2023
PRIMARY