Isoflupredone Chemical Properties

Melting point:

260-262°C (dec.)

alpha 

D23 +108° (c = 0.611 in ethanol); D23 +94° (alcohol)(Fried)

Boiling point:

566.7±50.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

DMSO (Slightly), Ethanol (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)

form 

Solid

pka

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|

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Isoflupredone Usage And Synthesis

Description

Isoflupredone, 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].

Chemical Properties

White Solid

Originator

Isoflupredon,Farmabios

Uses

Isoflupredone 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].

Definition

ChEBI: 9-Fluoroprednisolone is a 21-hydroxy steroid.

Manufacturing Process

A 100 ml broth culture containing a 0.1% yeast extract concentration, 9.0 ml of 0.2 M KH2PO4 and 9.0 ml of 0.2 M Na2HPO4 contained in a 300 ml Erlenmeyer flask, is seeded with 1 ml of a 24-h broth culture of Corynehacierium simplex (A. T, C. C. 6946). The flask is incubated at 28°C for 24 h. A second 300 ml Erlenmeyer flask containing 150 mg of sterile 9α- fluoro-4-pregnen-11β,17α,21-triol-3,20-diene in 5.0 ml acetone is inoculated with the 24 h culture of Corynebacterium simplex (A. T. C. C. 6946). The culture-containing steroid solution is incubated for 48 h at 28° to 30°C.
The product is extracted with chloroform and isolated by evaporation to dryness. Recrytstallizstion of the residue affords 9α-fluoro-δ1,4-pregnadiene- 11β,17α,21-triol-3.20-dione as a solid.

Therapeutic Function

Glucocorticoid

References

[1] Ma L, et al. Multiresidue analysis of glucocorticoids in milk by LC-MS/MS with low-temperature purification and dispersive solid-phase extraction. Journal of Separation Science, 2017; 40: 2759-2768.
[2] Wolf C, et al. Uterine nitric oxide levels and isofluopredone treatment effect in mares susceptible to persistent post-breeding endometritis. Animal Reproduction, 2016; 13: 100-104.
[3] Knych H, et al. Expression of inflammatory and structural matrix genes in synovial fluid following intra-articular administration of isoflupredone acetate to exercised horses. Equine Veterinary Journal, 2017; 50: 504-512.

Isoflupredone(338-95-4)Related Product Information

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• Prednisone 21-acetate
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• ciprocinonide
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