(S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one

Category	Human immunodeficiency Virus (HIV)
CAS	154598-52-4
Description	Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are highly specific and potent allosteric inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Efavirenz is an NNRTI that prevents RNA plus-strand initiation with an IC50 value of 17 nM. Efavirenz also inhibits the late stages of HIV-1 replication by interfering with HIV-1 Gag-Pol polyprotein processing. It has been used in combination therapy with drugs directed at the treatment of opportunistic infections such as HIV and cancer.

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Product Information

Synonyms	(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
IUPAC Name	(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
Molecular Weight	315.67
Molecular Formula	C14H9ClF3NO2
Canonical SMILES	C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(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
Boiling Point	340.6 °C at 760 mmHg
Melting Point	139-141°C
Flash Point	209.4±31.5 °C
Purity	> 98 %
Density	1.53 g/cm³
Solubility	In Vitro: DMSO: ≥ 38 mg/mL (120.38 mM)
Appearance	White to off-white (Solid)
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Complexity	519
Exact Mass	315.0273907
Index Of Refraction	1.582
In Vitro	Efavirenz is capable of inhibiting, with 95% inhibitory concentrations of ≤ 1.5 μM, a panel of nonnucleoside reverse transcriptase (RT) inhibitors (NNRTIs)-resistant mutant viruses, each of which expresses a single RT amino acid substitution. Efavirenz effectively inhibits several wild-type T-lymphoid cell line-adapted variants. Identical activity (IC95, 1.5 to 3.0 nM) is seen with wild-type primary isolates of the virus in both primary lymphoid and monocytoid cell cultures.
In Vivo	After i.v. administration, Efavirenz is cleared rapidly from rats, but it is cleared considerably more slowly from monkeys. The oral bioavailability in rats is 16%. In monkeys, the half-life of Efavirenz after administration of a 1 mg/kg i.v. dose exceeded 2.5 h. Administration to monkeys of oral doses as fine suspensions in 0.5% aqueous methylcellulose yields consistently high levels in plasma. A 2.0 mg/kg dose produces peak levels of 0.5 μM at approximately 3.0 h.
PSA	38.33000
Target	Ki: 2.93 nM (HIV-1 RT)
Vapor Pressure	0.0±1.1 mmHg at 25°C
XLogP3-AA	4