Chemical Component Summary

Name(-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE
SynonymsDMP-266; Efavirenz
Identifiers(4S)-6-chloranyl-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
FormulaC14 H9 Cl F3 N O2
Molecular Weight315.675
TypeNON-POLYMER
Isomeric SMILESc1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F
InChIInChI=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
InChIKeyXPOQHMRABVBWPR-ZDUSSCGKSA-N

Chemical Details

Formal Charge0
Atom Count30
Chiral Atom Count1
Bond Count32
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00625 
NameEfavirenz
Groups
  • approved
  • investigational
DescriptionEfavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1. For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen. Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.
Synonyms
  • Efavirenzum
  • (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one
  • (S)-6-chloro-4-(Cyclopropylethynyl)-1,4-dihydro-(S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
  • 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one
  • Efavirenz
Brand Names
  • Jamp-efavirenz
  • Auro-efavirenz-emtricitabine-tenofovir
  • Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate
  • Sustiva 50mg
  • Teva-efavirenz/emtricitabine/tenofovir
IndicationFor use in combination treatment of HIV infection (AIDS)
Categories
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antiinfectives for Systemic Use
  • Antiviral Agents
  • Antivirals for Systemic Use
ATC-Code
  • J05AR06
  • J05AG03
  • J05AR11
CAS number154598-52-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Reverse transcriptase/RNaseHPISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninducer
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknownsubstrate,inducer
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor,inducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL223228
PubChem 64139
ChEMBL CHEMBL223228
ChEBI CHEBI:119486
CCDC/CSD KUVYUW, HUDRAC, AJEYAQ01, QUSREC, AJEYAQ03, XICSAF, QUSREC01