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| | Fluocortolone Basic information |
| Product Name: | Fluocortolone | | Synonyms: | (6s,8s,9r,10s,11s,13s,14s,16r,17s)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one;6-alpha-fluoro-11-beta,21-dihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione;methylfluorodehydrocorticosterone;Fluocortolon;Fluorocortolone;SH 742;SH-742;(6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one | | CAS: | 152-97-6 | | MF: | C22H29FO4 | | MW: | 376.46 | | EINECS: | 205-811-5 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Steroids | | Mol File: | 152-97-6.mol |  |
| | Fluocortolone Chemical Properties |
| Melting point | 113-116°C | | alpha | D20 +100° (dioxane) | | Boiling point | 537.4±50.0 °C(Predicted) | | density | 1.1001 (estimate) | | vapor pressure | 0.001Pa at 25℃ | | storage temp. | Refrigerator | | solubility | Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly) | | form | Solid | | pka | 12.98±0.10(Predicted) | | color | Pale Yellow to Yellow | | Water Solubility | 204mg/L at 20℃ | | LogP | 2.3 at 25℃ |
| | Fluocortolone Usage And Synthesis |
| Chemical Properties | Pale Yellow Solid | | Originator | Ultralan,Schering,W. Germany,1965 | | Uses | Fluocortolone is a glucocorticoid used in the treatment of several conditions, including hemorrhoids. Fluocortolone is similar to Fluocortin, but with one less keto group. | | Definition | ChEBI: Fluocortolone is a 21-hydroxy steroid. | | Manufacturing Process | (a) 16α-Methyl-6α-Fluoro-δ4-11β,21-Diol-3,20-Dione:16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate (MP 132°/134° to 138°C, UVε238=
15,000) is hydroxylated with Curvularia lunata in 11β-position using the
fermentation method whereby the 21-acetate group is simultaneously
saponified. The hitherto unknown starting material 16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate is obtained from 16α-methyl-δ5-
pregnene-3β,21-diol-20-one-21-acetate, MP 152° to 154°C, by the addition of
bromofluorine (from N-bromoacetamide and hydrogen fluoride) onto the 5-6
double bond, oxidation of the 3β-hydroxyl group with chromic acid,
introduction of the δ4-double bond by splitting of the hydrogen bromide and
acid isomerization of the 6β-fluoro substituent to the 16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate. By chromatographic purification on
silica gel the 16α-methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is: MP
166°/167° to 171°C.
(b) 16α-Methyl-6α-Fluoro-δ4-Pregnene-11β,21-Diol-3,20-Dione-21-Acetate:By
reaction of the compound of (a) with acetic anhydride in pyridine at room
temperature, the acetate is obtained and recrystallized from ethyl acetate, MP
248°/249° to 251°C.
(c) 16α-Methyl-6α-Fluoro-δ1,4-Pregnadiene-11β,21-Diol-3,20-Dione:16α-
methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is dehydrogenated with
Corynebacterium simplex. The extraction residue is subjected to
chromatography on silica gel and after recrystallization there is obtained from
methylene chloride-isopropyl ether 16α-methyl-6α-fluoro-δ1,4-pregnadiene-
11β,21-diol-3,20-dione, MP 180°/181° to 182°C. | | Therapeutic Function | Glucocorticoid | | Flammability and Explosibility | Notclassified |
| | Fluocortolone Preparation Products And Raw materials |
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