Beclomethasone

Title: Beclomethasone
CAS Registry Number: 4419-39-0
CAS Name: (11b,16b)-9-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
Additional Names: 9a-chloro-16b-methyl-1,4-pregnadiene-11b,17a,21-triol-3,20-dione; 9a-chloro-16b-methylprednisolone
Molecular Formula: C22H29ClO5
Molecular Weight: 408.92
Percent Composition: C 64.62%, H 7.15%, Cl 8.67%, O 19.56%
Literature References: Glucocorticoid. Prepn of free alcohol and 21-acetate: GB 912378 (1962 to Merck & Co.); of 21-acetate: GB 901093 (1962 to Schevico); of mono and diesters: J. Elks et al., BE 649170; eidem, US 3312590 (1964, 1967 both to Glaxo). Symposium on clinical studies: Br. J. Clin. Pharmacol. 4, Suppl. 3, 249S-312S (1977). Use in chronic asthma in children: M. Rao et al., J. Asthma 19, 21 (1982); in treatment of asthma in steroid-independent adults: V. A. Malfitan, Clin. Ther. 4, 472 (1982). Review of use in rhinitis: P. Small et al., Ann. Allergy 49, 127 (1982); of pharmacology, side effects and use in asthma and allergic rhinitis: R. N. Brogden et al., Drugs 28, 99-126 (1984).
Derivative Type: Dipropionate
CAS Registry Number: 5534-09-8
Manufacturers' Codes: Sch-18020W
Trademarks: Aerobec (3M Pharma); Aldecin (Schering-Plough); Anceron (Schering-Plough); Andion (GEA); Beclacin (Kaigai); Becloforte (GSK); Beclomet (Orion); Beclorhinol (Lindopharm); Beclovent (GSK); Becodisks (GSK); Beconase (GSK); Beconasol (GSK); Becotide (GSK); Clenil-A (Chiesi); Entyderma (Taiyo); Inalone (Lampugnani); Korbutone (Nippon Glaxo); Propaderm (GSK); Qvar (3M); Rino-Clenil (Chiesi); Sanasthmax (GSK); Vancenase (Schering-Plough); Vanceril (Schering-Plough); Viarex (Schering-Plough); Viarox (Byk Gulden)
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 + ether, mp 117-120° (dec). [a]D +98.0° (c = 1.0 in dioxane). uv max (ethanol): 238 nm (e 15990).
Melting point: mp 117-120° (dec)
Optical Rotation: [a]D +98.0° (c = 1.0 in dioxane)
Absorption maximum: uv max (ethanol): 238 nm (e 15990)
Therap-Cat: Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).
Keywords: Antiallergic (Steroidal, Nasal); Antiasthmatic (Steroidal, Inhalant); Glucocorticoid.
Beclotiamine Befloxatone Befunolol Behenic Acid Belatacept

Beclometasone dipropionate
Beclometasone dipropionate.png
Beclometasone-dipropionate-3D-balls.png
Systematic (IUPAC) name
(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. B3 (AU)
Legal status Pharmacy Only (S2) (AU) POM (UK)
Routes Oral & nasal inhalation, topical
Pharmacokinetic data
Bioavailability Converted to beclometasone-17-monopropionate (17-BMP) during absorption
Protein binding 87% of 17-BMP to albumin and transcortin
Metabolism By esterase enzymes found in most tissues
Half-life 2.8 hours
Excretion  ?
Identifiers
CAS number 5534-09-8 YesY
ATC code A07EA07 D07AC15, R01AD01, R03BA01
PubChem CID 21700
DrugBank DB00394
ChemSpider 20396 YesY
UNII 5B307S63B2 YesY
ChEBI CHEBI:3002 YesY
ChEMBL CHEMBL1200500 N
Chemical data
Formula C28H37ClO7 
Mol. mass 521.042 g/mol
 N (what is this?)  (verify)

Beclometasone dipropionate (INN modified) or beclomethasone dipropionate (USAN, former BAN) is a potent glucocorticoid steroid. It is a prodrug of the free form, beclometasone (INN). In the form of an inhaler (e.g. Clenil, Qvar), a wide number of brands of which are available, it is used for the prophylaxis of asthma. As a nasal spray (e.g. Beconase, alanase, Vancenase) or nasal aerosol (e.g. Qnasl), it is used for the treatment of rhinitis (e.g. hay fever) and sinusitis. In some instances, it is used by oral pathologists in the treatment of unusually severe aphthous ulcers.

As a cream or ointment (trade name Propaderm), it is used to treat severe inflammatory skin disorders (e.g. eczema) unresponsive to less potent steroids, but is generally avoided in the treatment of psoriasis due to the risk of rebound on withdrawal.

It is also licensed to treat ulcerative colitis in conjunction with doses of 5-aminosalicylates in the United Kingdom in the form of a gastric acid-resistant, periodic release tablet marketed under the brand name Clipper.