Alclometasone

Title: Alclometasone
CAS Registry Number: 67452-97-5
CAS Name: (7a,11b,16a)-7-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
Additional Names: 7a-chloro-16a-methylprednisolone
Molecular Formula: C22H29ClO5
Molecular Weight: 408.92
Percent Composition: C 64.62%, H 7.15%, Cl 8.67%, O 19.56%
Literature References: Non-fluorinated corticosteroid with low systemic effects. Prepn: M. J. Green et al., US 4076708; M. J. Green, H. J. Shue, US 4124707 (both 1978 to Schering); M. J. Green et al., J. Steroid Biochem. 11, 61 (1979); H. J. Shue et al., J. Med. Chem. 23, 430 (1980). Topical anti-inflammatory activity of the 17,21-dipropionate: B. Lutsky et al., Arzneim.-Forsch. 29, 992 (1979); M. J. Green et al., ibid. 30, 1618 (1980).
Properties: Crystals from acetone/hexane, mp 176-179°. [a]D26 +47.5° (c = 0.3 in DMF). uv max (methanol): 242 nm (e 15500).
Melting point: mp 176-179°
Optical Rotation: [a]D26 +47.5° (c = 0.3 in DMF)
Absorption maximum: uv max (methanol): 242 nm (e 15500)
Derivative Type: 17,21-Dipropionate
CAS Registry Number: 66734-13-2
Manufacturers' Codes: Sch-22219
Trademarks: Aclosone (Schering); Aclovate (GSK); Almeta (Shionogi); Delonal (Essex); Legederm (Schering); Modrasone (Schering); Perderm (Schering)
Molecular Formula: C28H37ClO7
Molecular Weight: 521.04
Percent Composition: C 64.54%, H 7.16%, Cl 6.80%, O 21.49%
Properties: Crystals from acetone/methanol/isopropyl ether, mp 212-216°. [a]D26 +42.6° (c = 0.3 in DMF). uv max (methanol): 242 nm (e 15600).
Melting point: mp 212-216°
Optical Rotation: [a]D26 +42.6° (c = 0.3 in DMF)
Absorption maximum: uv max (methanol): 242 nm (e 15600)
Therap-Cat: Anti-inflammatory (topical).
Keywords: Glucocorticoid.
Aldicarb Aldioxa Aldol Aldosterone Aldrin

Alclometasone
Alclometasone.svg
Systematic (IUPAC) name
[7-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate
Clinical data
Trade names Aclovate
AHFS/Drugs.com monograph
MedlinePlus a604021
Legal status Rx Only (US)
Routes topical
Identifiers
CAS number 66734-13-2 YesY
ATC code D07AB10 S01BA10
PubChem CID 5311000
DrugBank DB00240
ChemSpider 4470541 YesY
UNII 136H45TB7B YesY
KEGG D01820 YesY
ChEBI CHEBI:53776 YesY
ChEMBL CHEMBL1201361 N
Chemical data
Formula C28H37ClO7 
Mol. mass 521.042 g/mol
 N (what is this?)  (verify)

Alclometasone is synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent.

The prodrug alclometasone dipropionate is marketed as Aclovate by GlaxoSmithKline.