Chemistry:Fluprednidene acetate

Short description: Pharmaceutical drug

Fluprednidene acetate

Clinical data
Trade names	Decoderm, others
Other names	[2-[(9R,17R)-9-Fluoro-11,17-dihydroxy-10,13-dimethyl-16-methylidene-3-oxo-7,8,11,12,14,15-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical (cream)
ATC code	D07AB07 (WHO) D07XB03 (WHO) (combinations)
Identifiers
IUPAC name 2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-13-methylidene-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
CAS Number	1255-35-2 Y
PubChem CID	9980241
DrugBank	DB08970 N
ChemSpider	8155833
UNII	GE65DV564S
KEGG	D07980
ChEBI	CHEBI:135700
Chemical and physical data
Formula	C24H29FO6
Molar mass	432.488 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)OCC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)O
InChI InChI=1S/C24H29FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,17-19,28,30H,1,5-6,9,11-12H2,2-4H3/t17-,18-,19-,21-,22-,23-,24-/m0/s1 Key:DEFOZIFYUBUHHU-IYQKUMFPSA-N
NY (what is this?)  (verify)

Fluprednidene acetate (trade name Decoderm among others) is a moderately potent glucocorticoid used in form of a cream to treat skin inflammations such as atopic dermatitis and contact dermatitis.

Contraindications

Similar to other corticoids, fluprednidene acetate is contraindicated in skin conditions that are caused by bacteria, fungi or viruses, including acne, syphilis, tuberculosis, as well as in rosacea and in children under two years of age. Insufficient data are available to judge safety during pregnancy and lactation.

Side effects

Side effects are rare and include typical corticoid reactions such as skin atrophy, telangiectasias, stretch marks, and steroid acne. They mostly occur when large skin areas (more than 10% of body surface) are treated, when treatment is continued over more than two to four weeks, under occlusive therapy or therapy in skin folds. Hypersensitivity reactions have also been described.

Pharmacology

Under open treatment, little substance reaches the circulation, and the body's own blood corticoid (cortisol) levels are not influenced. Under occlusive therapy, cortisol levels can be decreased because of a feedback reaction via the hypothalamic–pituitary–adrenal axis. This reaction is however not clinically significant.

External links

• CID 92921 from PubChem — Fluprednidene (without acetate)