Wednesday, March 4, 2015


Common name: Efavirenz; DMP-266; L-743725; L-741211; L-743726; Stocrin; Sustiva
Trademarks:  Stocrin; Sustiva
Molecular Formula: C14H9ClF3NO2 
CAS Registry Number: 154598-52-4
CAS Name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
Molecular Weight: 315.675
SMILES: FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1
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
Activity: AIDS Medicines, Anti-HIV Agents, Anti-infective Therapy, Reverse Transcriptase Inhibitors;  Highly Active Antiretroviral Therapy; HAART Therapy
Status: Launched 1998
Originator: Bristol-Myers Squibb/Merck

Efavirenz synthesis: Synth Commun 1997, 27(24), 4373-4384 (An initial attempt to synthesize Efavirenz. Authors have reported poor yields as well as operational reasons for not extending it to large scale)
Efavirenz synthesis: Antimicrob Agents Chemother 1995, 39(12), 2602-2605
Efavirenz synthesis: US5519021A
Efavirenz synthesis (Asymmetric): J Org Chem 199863(23), 8536-8543
Efavirenz Intermediate:

1. Pierce, M. E.; et. al. Practical Asymmetric Synthesis of Efavirenz (DMP 266), an HIV-1 Reverse Transcriptase Inhibitor. J Org Chem 1998, 63(23), 8536-8543.
2. Radesca, L. A.; et. al. Synthesis of HIV-1 reverse transcriptase inhibitor DMP 266. Synth Commun 1997, 27(24), 4373-4384.
3. Young, S. D.; et. al. L-743, 726 (DMP-266): a novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother 1995, 39(12), 2602-2605.
4. Young, S. D.; et. al. Benzoxazinones as inhibitors of HIV reverse transcriptase. US5519021A