HALOBETASOL PROPIONATE
Halobetasol Propionate
CAS: 66852-54-8
Molecular Formula: C25H31ClF2O5
HALOBETASOL PROPIONATE - Names and Identifiers
HALOBETASOL PROPIONATE - Physico-chemical Properties
| Molecular Formula | C25H31ClF2O5 |
| Molar Mass | 484.96 |
| Density | 1.31±0.1 g/cm3(Predicted) |
| Melting Point | 213-215°C |
| Boling Point | 570.7±50.0 °C(Predicted) |
| Flash Point | 298.944°C |
| Solubility | Dioxane (Sparingly), DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Crystallization from dichloromethane-ether |
| Color | White to Off-White |
| pKa | 12.55±0.70(Predicted) |
| Storage Condition | Refrigerator |
| Refractive Index | 1.551 |
| MDL | MFCD00866013 |
| Physical and Chemical Properties | Crystallization from dichloromethane-diethyl ether, melting point 220-21C. |
| In vitro study | Halobetasol propionate acts by inducing phospholipase A2 inhibitory proteins, which are collectively referred to as Lipocortin. These proteins are postulated to control the biosynthesis of effective mediators of inflammation, such as prostaglandins and leukotrienes, by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. However, the initial interaction is due to the drug binding to the cytoplasmic glucocorticoid receptor. Upon binding to the receptor, the newly formed receptor-ligand complex translocates into the nucleus and binds to a number of glucocorticoid response elements (GRE) in the promoter region of the target gene. The DNA-binding receptor then interacts with basal transcription factors to enhance the expression of specific target genes. |
HALOBETASOL PROPIONATE - Risk and Safety
| HS Code | 2937220000 |
HALOBETASOL PROPIONATE - Nature
Open Data Verified Data
crystallized from dichloromethane-diethyl ether, melting point 220-221 °c.
Last Update：2024-01-02 23:10:35
HALOBETASOL PROPIONATE - Preparation Method
Open Data Verified Data
6a,9-= fluoro-iip.17.21-trihydroxy 16p-pregnane-1, 4-alkene -3,20-= keto-17 propionate (I) and methanesulfonyl chloride, reaction in Pyridine at 5 ° C. To obtain a compound, which reacts with lithium chloride in dimethylformamide at 100 ° C, oubetasol propionate was obtained.
Last Update：2022-01-01 09:24:00
HALOBETASOL PROPIONATE - Use
Open Data Verified Data
developed by the Swiss company Ciba-Geigy, launched in 1991. Local corticosteroids. For the relief of inflammatory and pruritic conditions of the skin sensitive to corticosteroids.
Last Update：2022-01-01 09:24:00
HALOBETASOL PROPIONATE - Reference Information
| Overview | halofibretasone propionate is a 6 α-fluorocorticosteroid. These drugs have an exclusive 6-fluoro substituent in the α-(flat) configuration. Derivatives of these compounds, such as difluropine diacetate, halotaxol propionate, difluoromethasone acetate, and the like, have also been shown to have high anti-inflammatory activity. |
| indication | halofibrate propionate is a topical treatment for adults with plaque psoriasis. |
| preparation | to 17-hydroxy -9 β,11 β-epoxy -16-β-methyl progestin -1, to a solution of 4-dien-3, 20-diketo-21-acetate (5.0g) in isopropylidene acetate (50ml) was added concentrated sulfuric acid (0.25ml). The mixture was stirred for 2 H, excess sulfuric acid was neutralized with triethylamine, the resulting solution was evaporated in vacuo, the residue was dissolved in acetonitrile (50ml) and F-TEDA(8.0g) was added. The resulting mixture was stirred for 1 hour, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo. The residue was triturated with methanol to obtain pure 6 α-fluoro -17-hydroxy -9 β,11 β-epoxy -16-β-methyl -1, 4-diene-3, 20-diketone 21-acetate. 6 Alpha-fluoro -17-hydroxy -9 Beta, 11 beta-epoxy -16 beta-methyl pregnancy -1,4-diene -3, A cooled (-10 to -15) solution of 20-diketo-21-acetate (1.62g) in 70% hydrofluoric acid (25ml) was stirred for 3.5 hours. The solution was then diluted with 250ml, stirred for 1 hour and the precipitate of difluoropone 21-acetate was filtered off. A solution of potassium carbonate (0.7g) and water (7ml) was added with stirring to a suspension of difluoropone 21-acetate (g) in methanol (15ml) and stirring was continued for 3 hours, the solution was concentrated in vacuo and the residue was diluted with water. The resulting suspension was filtered to give difluoropone, which was washed with water and dried. A mixture of difluoropone (1g) and PTSA(0.3g) was added to N,N-dimethylacetamide (10ml) and stirred until dissolved. To this solution was added trimethyl orthoacetate (1ml). The solution was stirred for 5 hours. The solution was then diluted with 40ml of water and stirred for an additional 3 hours. The formed precipitate of difluoropone 17-acetate was filtered off, washed with water and dried. Difluropine 17-propionate was prepared in a similar manner. Triethylamine (4ml) was added to a solution of difluoropone 17-propionate (3G) in N,N-dimethylformamide (30ml) followed by methanesulfonyl chloride (1.4ml). The resulting suspension was stirred for 1 hour and hydrochloric acid (10ml,2N) was added. The suspension was stirred for an additional 1 hour and the precipitate of difluoron 17-propionate -21-methanesulfonate formed was filtered, washed and filtered. Difluropine 17-propionate -21-methanesulfonate (1.5g) was dissolved in DMA(10ml), lithium chloride (0.2g) was added, and the mixture was heated to 100-110 °c and stirred for 3 hours. The solution was then cooled to 50-55 °c, diluted with 10ml and stirred for 2 more hours. The precipitate of halotaxol propionate formed was filtered, washed with water and dried. |
| biological activity | Halobetasol proponate (BMY-30056, CGP-14458) is an anti-inflammatory and dermatological agent commonly used to treat psoriasis. Halobetasol prolate is thought to exert its effect by inducing the phospho-holiase A2 (PLA2) inhibitor protein. |
| Target | Value |
| Use | topical corticosteroids. For the relief of inflammatory and pruritic conditions of the skin sensitive to corticosteroids. |
| production method | 6 α, 9-difluoro-11 β,17,21-trihydroxy-16 β-pregnane-1, 4-diene-3, 20-diketo-17 propionate (I) and methanesulfonyl chloride, reaction in Pyridine at 5 °c for 21H gave compound (II). (Ii) reaction with lithium chloride in dimethylformamide at 100 ° C. Affords oubetasol propionate. |
Last Update：2024-04-10 22:29:15
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HALOBETASOL PROPIONATE
B-环柠檬醛
(1-甲氧基环丙基)甲醇
(3-丙基)三甲基氯化铵
二苯基[4-(三苯基硅烷基)苯基]氧膦
2-(2,6-二氯-苄氧基甲基)-吡咯烷盐酸盐
2-甲基-2,4,5,6-四氢吡咯并[3,4-c]吡唑盐酸盐
SODIUM POTASSIUM CHLORIDE COTRANSPORTER 2, RAT, 15AA NEAR CT
1-Azabicyclo[2.2.2]octan-3-ol, 2-[(2-chloro-6-fluorophenyl)methylene]-, phenylcarbamate (ester) (9CI)
(2S,3S)-2-((((9H-芴-9-基)甲氧基)羰基)(甲基)氨基)-3-甲基戊酸
B-环柠檬醛
(1-甲氧基环丙基)甲醇
(3-丙基)三甲基氯化铵
二苯基[4-(三苯基硅烷基)苯基]氧膦
2-(2,6-二氯-苄氧基甲基)-吡咯烷盐酸盐
2-甲基-2,4,5,6-四氢吡咯并[3,4-c]吡唑盐酸盐
SODIUM POTASSIUM CHLORIDE COTRANSPORTER 2, RAT, 15AA NEAR CT
1-Azabicyclo[2.2.2]octan-3-ol, 2-[(2-chloro-6-fluorophenyl)methylene]-, phenylcarbamate (ester) (9CI)
(2S,3S)-2-((((9H-芴-9-基)甲氧基)羰基)(甲基)氨基)-3-甲基戊酸