CHEBI:119486 - efavirenz

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ChEBI Name efavirenz
ChEBI ID CHEBI:119486
Definition 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47396, CHEBI:4760, CHEBI:190461
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Formula C14H9ClF3NO2
Net Charge 0
Average Mass 315.67500
Monoisotopic Mass 315.027
InChI InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
InChIKey XPOQHMRABVBWPR-ZDUSSCGKSA-N
SMILES FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC1CC1
Roles Classification
Biological Role(s): HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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ChEBI Ontology
Outgoing efavirenz (CHEBI:119486) has role antiviral drug (CHEBI:36044)
efavirenz (CHEBI:119486) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
efavirenz (CHEBI:119486) is a acetylenic compound (CHEBI:73474)
efavirenz (CHEBI:119486) is a benzoxazine (CHEBI:46969)
efavirenz (CHEBI:119486) is a cyclopropanes (CHEBI:51454)
efavirenz (CHEBI:119486) is a organochlorine compound (CHEBI:36683)
efavirenz (CHEBI:119486) is a organofluorine compound (CHEBI:37143)
IUPAC Name
(4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one
Synonyms Sources
(-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE PDBeChem
(S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one ChemIDplus
(S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one ChEMBL
6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one ChEMBL
Efavirenz KEGG COMPOUND
Manual Xrefs Databases
989 DrugCentral
C08088 KEGG COMPOUND
D00896 KEGG DRUG
DB00625 DrugBank
Efavirenz Wikipedia
EFZ PDBeChem
EP582455 Patent
HMDB0014763 HMDB
LSM-5526 LINCS
US5519021 Patent
View more database links
Registry Numbers Types Sources
154598-52-4 CAS Registry Number KEGG COMPOUND
154598-52-4 CAS Registry Number ChemIDplus
7387333 Beilstein Registry Number Beilstein
7387333 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10576692 PubMed citation ChEMBL
10673109 PubMed citation ChEMBL
25017682 PubMed citation Europe PMC
Last Modified
22 February 2017