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A7583158

Efavirenz , 10mMinDMSO , 154598-52-4

Synonym(s):
(4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one;(4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one;Aryl halide chemistry informer library compound X17;Efavirenz

CAS NO.:154598-52-4

Empirical Formula: C14H9ClF3NO2

Molecular Weight: 315.67

MDL number: MFCD05662344

EINECS: 620-492-6

Pack Size Price Stock Quantity
1ml RMB159.20 In Stock
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Update time: 2022-07-08

PRODUCT Properties

Melting point: 139-141°C
Boiling point: 340.6±42.0 °C(Predicted)
alpha  D20 -84.7° (c = 0.005 g/ml in CH3Cl); D25 -94.1° (c = 0.300 in methanol)
Density  1.53±0.1 g/cm3(Predicted)
Flash point: 2℃
storage temp.  -20°C
solubility  DMSO: soluble15mg/mL, clear
pka 10.2(at 25℃)
form  powder or crystals
color  white to beige
optical activity [α]/D -90 to -100°, c = 1 in methanol
Water Solubility  8mg/L(temperature not stated)
λmax 247nm(MeOH)(lit.)
Merck  14,3521
BCS Class 4
EPA Substance Registry System 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)- (154598-52-4)

Description and Uses

Efavirenz D5 was launched as Sustiva in the US for the treatment of infection by HIV, the virus causing AIDS, in combination with other anti-retroviral agents.
Efavirenz D5 is a non-nucleoside reverse transcriptase inhibitor (NNRTI) belonging to the 3,1-benzoxazin-2-one chemical class. It is the third non-nucleoside reverse transcriptase inhibitor to have been launched to date, after Nevirapine (1996) and Delavirdine (1997), increasing the arsenal of anti-HIV drugs for treating infected patients in dual or triple combination with nucleoside or other non-nucleoside RTIs, or protease inhibitors.
Efavirenz D5 can be obtained by two related ways of six steps from 4-chloroaniline ; one of them is based on asymmetric synthesis by enantioselective addition of an acetylide to a trifluoroacetophenone. The anti-HIV activity of Efavirenz D5 was demonstrated against most wild-type and clinical strains of HIV-1, including those with the most frequently observed mutations. Efavirenz D5 has a better pharmacokinetic profile when compared with the preceding drugs of this class ; in particular, in a long-term experiment conducted in cynomolgus monkeys, Efavirenz D5 was shown to easily cross the blood brain barrier leading to an increase of the antiviral concentration in cerebrospinal fluid.

For use in combination treatment of HIV infection (AIDS)

Safety

Symbol(GHS) 
GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H302-H360-H410
Precautionary statements  P202-P264-P270-P273-P301+P312-P308+P313
Hazard Codes  N
Risk Statements  50
Safety Statements  61
RIDADR  UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous substances, liquid, n.o.s. HI: all (not BR)
WGK Germany  3
RTECS  DM3440000
HS Code  2934990002
Hazardous Substances Data 154598-52-4(Hazardous Substances Data)

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