Flumetasone

Flumetasone
Clinical data
Trade names	Flucort
Other names	Flumethasone (USAN)
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Topical
ATC code	D07AB03 (WHO) , D07XB01 (WHO) (combinations), QH02AB90 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Metabolism	Liver, CYP3A4-mediated
Identifiers
	IUPAC name (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one;
CAS Number	2135-17-3 ;
PubChem CID	16490;
ChemSpider	15632 ;
UNII	LR3CD8SX89;
KEGG	D04208 ;
ChEBI	CHEBI:34764 ;
ChEMBL	ChEMBL1201392 ;
CompTox Dashboard (EPA)	DTXSID2045365 ;
ECHA InfoCard	100.016.701
Chemical and physical data
Formula	C22H28F2O5
Molar mass	410.458 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F;
	InChI InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 ; Key:WXURHACBFYSXBI-GQKYHHCASA-N ;
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Flumetasone, also known as flumethasone,[1] is a corticosteroid for topical use.

It was patented in 1951 and approved for medical use in 1964.[2]

Chemistry

Flumethasone is 420 times as potent as cortisone in an animal model for anti-inflammatory activity.

Society and culture

Names

Trade names include Locacorten, Locorten, and Orsalin. It is available in combination with clioquinol, under the brand name Locacorten-Vioform (in some countries Locorten-Vioform), for the treatment of otitis externa and otomycosis. It is usually formulated as the pivalic acid ester prodrug called flumetasone pivalate.

Veterinary uses

In April 2023, the US Food and Drug Administration approved the first generic version of flumethasone (Bimasone), for certain diseases that cause inflammation in horses, dogs, and cats.[3] Flumetasone is recommended for the various rheumatic, allergic, dermatologic and other disease states that are known to be responsive to anti-inflammatory drugs (i.e., corticoids) in these species.[3]

In horses, flumetasone is approved for use for musculoskeletal conditions due to inflammation, such as bursitis (a painful condition that affects the fluid-filled sacs that cushion the bones, tendons and muscles near a horse’s joints, often in the hip or shoulder), carpitis (inflammation of the connective tissues near the horse’s carpus, which is comparable to the human wrist), osselets (arthritis in the fetlock joint of a horse, often in the front legs), and myositis (rapid muscle wasting, often in the horse’s hindquarters).[3]

In dogs, Bimasone is approved for use for musculoskeletal conditions due to inflammation of muscles or joints, such as arthritis, osteoarthritis, intervertebral disc disease, and myositis.[3] The drug has proven useful in treating canine ear infections (otitis externa) when used with topical medication for similar reasons.[3] It is also approved for certain acute and chronic skin conditions (dermatoses) from various causes to help control the itchy skin (pruritus), irritation, and inflammation associated with these conditions, and for use in treating allergic reactions, such as hives, urticaria (raised itchy rash on skin), and insect bites.[3] Flumetasone is also approved for treating shock in dogs, when administered intravenously.[3]

In cats, flumetasone is approved for certain acute and chronic skin conditions (dermatoses) from various causes to help control the itchy skin (pruritus), irritation, and inflammation associated with these conditions.[3]

References

Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents Properties and Synonyms. Dordrecht: Springer Netherlands. p. 122. ISBN 9789401144391.
Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 7 April 2023.
"FDA Approves Generic Flumethasone for Diseases in Cats, Dogs and Horse". U.S. Food and Drug Administration (FDA). 5 April 2023. Archived from the original on 7 April 2023. Retrieved 7 April 2023. This article incorporates text from this source, which is in the public domain.

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[1] Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents Properties and Synonyms. Dordrecht: Springer Netherlands. p. 122. ISBN 9789401144391.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 7 April 2023.

[FDA_Bimasone-3] "FDA Approves Generic Flumethasone for Diseases in Cats, Dogs and Horse". U.S. Food and Drug Administration (FDA). 5 April 2023. Archived from the original on 7 April 2023. Retrieved 7 April 2023. This article incorporates text from this source, which is in the public domain.