Efavirenz
EFAVIRENZ
CAS: 154598-52-4
Molecular Formula: C14H9ClF3NO2
Efavirenz - Names and Identifiers
| Name | EFAVIRENZ |
| Synonyms | EFAVIRENZ efavuirenz Efavirenz solution Efavirenz (200 mg) Efavirenz Ready Made Solution (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoroMethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoroMethyl)-, (4S)- |
| CAS | 154598-52-4 |
| EINECS | 620-492-6 |
| InChI | InChI=1/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 |
Efavirenz - Physico-chemical Properties
| Molecular Formula | C14H9ClF3NO2 |
| Molar Mass | 315.67 |
| Density | 1.53±0.1 g/cm3(Predicted) |
| Melting Point | 139-141°C |
| Boling Point | 340.6±42.0 °C(Predicted) |
| Specific Rotation(α) | D20 -84.7° (c = 0.005 g/ml in CH3Cl); D25 -94.1° (c = 0.300 in methanol) |
| Flash Point | 2℃ |
| Water Solubility | 8mg/L(temperature not stated) |
| Solubility | DMSO: soluble15mg/mL, clear |
| Vapor Presure | 8.53E-05mmHg at 25°C |
| Appearance | White to slightly pink crystalline powder |
| Color | white to beige |
| Maximum wavelength(λmax) | ['247nm(MeOH)(lit.)'] |
| Merck | 14,3521 |
| pKa | 10.2(at 25℃) |
| Storage Condition | -20°C |
| Refractive Index | 1.58 |
| MDL | MFCD05662344 |
| Use | Used as an antiviral drug |
| In vitro study | Efavirenz has a direct inhibitory effect on mitochondrial respiratory function in cultured malignant glioma and differentiated human neuroblastoma cells. ER stress markers, including the expression of CHOP and GRP78, the phosphorylation of eIF2a and the cleavage form of XBP1 were all upregulated after Efavirenz treatment. Efavirenz also enhanced the intracellular calcium capacity and induced morphological changes upon endoplasmic reticulum stress. Such effects are attenuated in cells with altered mitochondrial function (Rho). |
| In vivo study | In ApoE(-/-) mice, Efavirenz causes arteriosclerosis, but does not cause an increase in plaque progression at the concentrations and treatment times tested. |
Efavirenz - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50 - Very Toxic to aquatic organisms |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | 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 |
Efavirenz - Nature
Open Data Verified Data
white or off-white crystalline powder. mp 139~141 ℃;[a] o-84.7. (c-o.005g/mL chloroform);[a]5 -94.10cc = 0.300 methanol);pK 10.2.
Last Update：2024-01-02 23:10:35
Efavirenz - Preparation Method
Open Data Verified Data
p-chloroaniline was dissolved in chloroform and saturated aqueous sodium carbonate, and 2,2-= methylpropionyl chloride was added dropwise. After the addition, the mixture was stirred at room temperature, the solid was collected by filtration, the filtrate was separated into layers, and the separated chloroform layer was washed with brine, dried, and concentrated. The material obtained by concentration and the solid obtained above were recrystallized from boiling ethyl acetate-hexane to give N-2-= methylpropionyl-p-chloroaniline. The acylate was dissolved in Tetrahydrofuran, n-butyl lithium in hexane solution was added dropwise, stirred, then ethyl trifluoroacetate was added dropwise, hydrochloric acid and ethyl acetate were added, the organic layer was separated, washed with brine, dried, the mixture was concentrated under reduced pressure, and the resulting material was refluxed in hydrochloric acid, cooled, added with ethyl acetate, and made alkaline with concentrated aqueous ammonia. The organic layer was separated, washed with brine, dried, and concentrated to give 2-trifluoroacetyl-4-chloroaniline. The cyclopropylacetylene is dissolved in Tetrahydrofuran, and ethyl magnesium bromide is added dropwise to the ether {caveolated solution for reaction. After completion, 2-trifluoroacetyl -4-chloroaniline is added, A saturated aqueous solution of ammonium chloride was further added dropwise. The mixture was extracted with ethyl acetate and the extracts were combined, washed with brine, dried and concentrated to give an alkylated product. This and carbonyl diimidazole were dissolved in anhydrous tetrahydrofuran. The solvent was then distilled off under reduced pressure and ethyl acetate and water were added. The aqueous layer was extracted with ethyl acetate. The extracts and the organic layer were combined, washed with hydrochloric acid, saturated sodium bicarbonate and brine, dried and concentrated under reduced pressure to give racemic efaviram. It is reacted with (a) a camphoroyl chloride in dichloromethane, and then in n-butanol, hydrochloric acid is added to the reaction, and the optically active efaviram is obtained.
Last Update：2022-01-01 09:08:19
Efavirenz - Use
Open Data Verified Data
developed by Merck, USA, Dupont was first listed in the USA in February 1999 and in Canada, Germany and the UK in July of the same year. Non-nucleoside reverse transcriptase inhibitors. In combination with other Virus reverse transcriptase inhibitors for the treatment of HIV-1 of infected patients.
Last Update：2022-01-01 09:08:19
Efavirenz - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Efavirenz (Sustiva, Stocrin, DMP-266) is a synthetic, non-nucleoside reverse transcriptase inhibitor with antiviral activity. |
| Target | Value |
| Use | Used as antiviral drug Non-nucleoside reverse transcriptase inhibitor. Combined with other viral reverse transcriptase inhibitors for the treatment of HIV-1 infected patients. |
| production method | 127.57g p-chloroaniline dissolved in 1200ml chloroform and 1200ml saturated sodium carbonate aqueous solution, and 129ml 2,2-dimethylpropionyl chloride was added dropwise in 1h. After adding, stir at room temperature for 23h. Filtration collects solids, the filtrate is layered, and the separated chloroform layer is washed with salt water, dried and concentrated. The remainder and the obtained solid were recrystallized with boiled ethyl acetate-hexane to give 185.6g of white crystalline compound (I). 100g compound (I) is dissolved in 1L tetrahydrofuran, 387ml of hexane solution 2.5Inol/L n-butyl lithium is added dropwise at 0 ℃ and 1h, and the temperature is maintained at 5 ℃. After adding, stir at 0 ℃ for 1h. Add 115ml ethyl trifluoroacetate dropwise in 1h, add it, and stir for 30min. Add 5% hydrochloric acid and 1L ethyl acetate, separate the organic layer, wash with salt water, dry, and concentrate under reduced pressure to obtain 160g of yellow oil. It was suspended at 1 L3mol/L. Hydrochloric acid, reflux 24h. Cool, add 1L ethyl acetate, adjust to alkaline with concentrated ammonia. The organic layer is separated, washed with brine, dried, and concentrated under reduced pressure. The residue was developed by chromatography with 1.5kg silica gel 15% hexane solution of ethyl acetate. The obtained solid was recrystallized with boiling hexane to obtain 57g compound (II) with 54% yield and melting point of 91~92 ℃. 23g cyclopropyl acetylene is dissolved in 250ml tetrahydrofuran, and 116ml 3.0mol/L ethyl magnesium bromide ether solution is added dropwise in 1h. After addition, react at 0 ℃ for 1h and then at 40 ℃ for 3h. Cooling to 0 ℃, 15.56g of compound (II) was added in batches in 5min. After adding, stir at 0 ℃ for 1.5h, then add 700ml saturated ammonium chloride aqueous solution dropwise. Extract with 2 × 400ml ethyl acetate, the extracts are combined and washed with salt water, dried, and concentrated to obtain yellow solid. Recrystallization with boiling hexane to obtain 14.67g of compound (Ⅲ) and 2.1g from mother liquor. Melting point 153~154 ℃. 15.00g of compound (Ⅲ) and 41.98g of carbonyl diimidazole (1,1 '-carbonyldiimidazole) were dissolved in 250ml of anhydrous tetrahydrofuran and stirred at 55 ℃ for 24 hours. The solvent was distilled under reduced pressure, and 500ml of ethyl acetate and 400ml of water were added. Stratified, the water layer was extracted with ethyl acetate. The extract and the organic layer were combined, washed with 2 × 200ml of 2% hydrochloric acid, saturated sodium bicarbonate and salt water, dried, and concentrated under reduced pressure to obtain 16.42g solid. With ethyl acetate. Hexane was recrystallized to obtain 12.97g of pure white crystalline racemic Efavirenz with a melting point of 178~180 ℃. 12.97g of racemic Efavirenz, 1.02g of 4-dimethylaminopyridine and 14.22g(-)-camphor acyl chloride are dissolved in 350ml of dried dichloromethane, and 22.84ml of triethylamine is added under argon protection, ice bath cooling and stirring. Remove the ice bath and allow it to rise to room temperature, react. 75min. Add 500ml chloroform, wash with 10% citric acid twice, water and salt water once each. Dry, concentrate under reduced pressure. Add 200ml hexane to boil the residue, cool to room temperature, filter to collect solids, wash with a small amount of cold hexane, vacuum dry to obtain 7.79g compound (Ⅳ), melting point 164~165 ℃, purity (HPLC)99.2%. Under argon protection and 60 ℃, 7.50g compound (Ⅳ) was dissolved in 150ml n-butanol, then 10ml lmol/L hydrochloric acid was added, and the reaction was carried out at 60 ℃ for 72h. Neutralize with aqueous sodium bicarbonate and remove n-butanol under reduced pressure. Dissolve the residue in 150ml tetrahydrofuran, add 50ml 2mol/L lithium hydroxide, and react at room temperature for 3h. After dilution with ethyl acetate, wash with water twice and salt water once. Dry, concentrate under reduced pressure. The residue was recrystallized with hexane to obtain a Efavirenz of 3.43g white crystals with a melting point of 131~132 ℃. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:07
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