(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 507
• Molecular Formular: C14H9ClF3NO2
• Molecular Mass: 315.6749696
• Monoisotopic Mass: 315.02739087
• SMILES: Clc1cc2[C@@](OC(=O)Nc2cc1)(C#CC1CC1)C(F)(F)F
• Canonical SMILES: FC([C@@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: efavirenz
• Brand Name: Stocrin; Sustiva
• Synonyms: EFV; efavirenz; Efavirenz; (4R)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; (R)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; L 743725; ent-Efavirenz; (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE

Database IDs

• CAS Number: 154801-74-8; 154598-52-4
• PubChem SID: 160963970; 46506827
• PubChem CID: 64139

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.523443
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.4565263
• LogD (pH = 7.4): 4.4565234
• Log P: 4.4565263
• Molar Refractivity: 71.3423 cm^3
• Polarizability: 25.755894 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.89
• LOG S: -4.57
• Solubility (Water): 8.55e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 125-127°C
• Hydrophobicity(logP): 4.6

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB07709

Drug information: experimental

DrugBank - DB00625

• Drug Groups: approved; investigational
• Description: Efavirenz (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.
• Indication: For use in combination treatment of HIV infection (AIDS)
• Pharmacology: Efavirenz (dideoxyinosine, ddI) is an oral nucleoside reverse transcriptase inhibitor (NRTI). It is a synthetic purine derivative and, similar to zidovudine, zalcitabine, and stavudine. Efavirenz was originally approved specifically for the treatment of HIV infections in patients who failed therapy with zidovudine. Currently, the CDC recommends that Efavirenz be given as part of a three-drug regimen that includes another nucleoside reverse transcriptase inhibitor (e.g., lamivudine, stavudine, zidovudine) and a protease inhibitor or efavirenz when treating HIV infection.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites. These metabolites are essentially inactive against HIV-1.
• Half Life: 40-55 hours
• Protein Binding: 99.5-99.75%
• Elimination: Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.
• References: Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - E425005

A nonnucleoside HIV-1 reverse transcriptase inhibitor. Antiviral.

REFERENCES

• Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. Pubmed
• Young, S.D., et al.: Antimicrob. Ag. Chemother., 39, 2602 (1995)