Isoflupredone
Basic information
- CAS
338-95-4- Standard SMILES
C[C@]12C=CC(=O)C=C1CC[C@H]1[C@@H]3CC[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F- InChIKey
WAIJIHDWAKJCBX-BULBTXNYSA-N- Molecular formula
- C21H27FO5
- Average molar mass
- 378.4 g/mol
- Monoisotopic mass
- 378.18425212
Overview
9-Fluoroprednisolone is a 21-hydroxy steroid.
Names & identifiers
- Preferred name
- Isoflupredone
- IUPAC
- (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- English name
- Isoflupredone
- Molecular formula
- C21H27FO5
- Molecular weight
- 378.43
Names & synonyms
ISOFLUPREDONE338-95-49-Fluoroprednisolonedelta-FluorocortisoneIsoflupredonaIsoflupredonumHYS0B45Z2SDTXSID101009333Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-, (11beta)-9 alpha-fluoroprednisoloneRefChem:56803DTXCID401436163
Show more names
9α-FluoroprednisoloneNSC 12174Eflornison9α-Fluoro-1-cortisol9a-fluoroprednisoloneIsoflupredone USP/EP/BPIsoflupredone in Methanol
pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-, (11 beta)-(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta(a)phenanthren-7-one206-422-3(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one(11beta)-9-fluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one(8S,9R,10S,13S,14S,17R)-9-Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-oneDeltafludrocortisone
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 775
Experimental & physicochemical properties
LogP1.51
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 260 · 260-262°C (dec.)
- alpha
- 23 · D23 +108° (c = 0.611 in ethanol); D23 +94° (alcohol)(Fried)
- Boiling point
- 566.7 · 566.7±50.0 °C(Predicted)
- Density
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Ethanol (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 12.1 · 12.10±0.70(Predicted)
- color
- White to Pale Brown
- InChIKey
- WAIJIHDWAKJCBX-MPVZUUJONA-N
- SMILES
- [C@@]12([H])CCC3=CC(=O)C=C[C@]3(C)[C@@]1(F)[C@@H](O)C[C@]1(C)[C@@](CC[C@@]21[H])(O)C(=O)CO |&1:0,10,12,14,17,19,22,r|
Chemistry & industry
Applications
DescriptionIsoflupredone, also known as deltafludrocortisone and 9α-fluoroprednisolone, is a synthetic glucocorticoid corticosteroid which was never marketed. Its acetate ester is isoflupredone acetate whch is widely used in veterinary medicine[1].
UsesIsoflupredone is an anti-inflammatory. Isoflupredone could be used as an internal standard in the determination of 12 glucocorticoids in bovine milk through liquid chromatography with tandem mass spectrometry[1]. It could be used to treat endometritis by increasing pregnancy rates[2]. Isoflupredone acetate is one of four Food and Drug Administration approved corticosteroids for intra-articular use in horses[3].
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 9-Fluoroprednisolone is a 21-hydroxy steroid.
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Compound notes
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