| Identification | Back Directory | [Name]
Fluocortolone | [CAS]
152-97-6 | [Synonyms]
SH 742
SH-742
flucortolone
Fluocortolon
FLUOCORTOLONE
FLUORCORTOLONE
Fluorocortolone
Fluocortolone USP/EP/BP
Fluocortolone Impurity 13
methylfluorodehydrocorticosterone
Fluocortolone Pivalate EP Impurity A
17alpha-propyl-5alpha-androstan-3-one
Fluocortolone (Fluocortolone Pivalate EPImpurity A)
Fluocortolone Pivalate EP Impurity A (Fluocortolone)
16α-Methyl-6α-fluoro-1,4-pregnadien-11β,21-diol-3,20-dione
(6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16-Methylpregna-1,4-diene-3,20-dione
6-alpha-fluoro-11-beta,21-dihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,21-dihydroxy-16-methyl-, (6α,11β,16α)-
Fluocortolone Pivalate Impurity 1 (Fluocortolone Pivalate EP Impurity A)(Fluocortolone)
6-fluoro-11-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
(6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-17-glycoloyl-11-hydroxy-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
(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
(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
(6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyethanoyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one | [EINECS(EC#)]
205-811-5 | [Molecular Formula]
C22H29FO4 | [MDL Number]
MFCD00867463 | [MOL File]
152-97-6.mol | [Molecular Weight]
376.46 |
| Chemical Properties | Back Directory | [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℃ |
| Hazard Information | Back Directory | [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 | [storage]
-20°C |
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