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Beclometasone dipropionate
Systematic (IUPAC) name
(8S,9R,10S,11S,13 S,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-3 H-cyclopenta[a]phenanthren-17-yl propionate
Identifiers
CAS number 5534-09-8
ATC code A07EA07 D07AC15, R01AD01, R03BA01
PubChem 21700
DrugBank APRD00564
ChemSpider 20396
Chemical data
Formula C 28H37ClO7  
Mol. mass 521.042 g/mol
SMILES eMolecules & PubChem
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  ?
Therapeutic considerations
Pregnancy cat. B3(AU)
Legal status Pharmacy Only (S2) (AU) POM (UK)
Routes Oral & nasal inhalation, topical
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Beclometasone dipropionate (INN modified) or beclomethasone dipropionate (USAN, former BAN), also referred to as beclometasone (INN), is a potent glucocorticoid steroid. In the form of an inhaler (e.g. Becotide, 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, Vancenase), it is used for the treatment of rhinitis (e.g. hayfever) and sinusitis. In some instances it is used by oral pathologists in the treatment of unusually severe canker sores.

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 licenced to treat ulcerative colitis in conjunction with doses of 5-aminosalicylates in the United Kingdom in the form of a gastro resistant, periodic release tablet marketed under the brand name Clipper.

Chemistry

It is a white to creamy-white, odorless powder which is very slightly soluble in water, very soluble in chloroform, and freely soluble in acetone and in ethanol.

Side effects

Occasionally it may cause a cough upon inhalation. Deposition on the tongue and throat may promote oral candidiasis which appears as a white coating, possibly with irritation.[1][2][3] This may usually be prevented by rinsing the mouth with water after using the inhaler. Other side effects may rarely include: a smell not dissimilar to burning plastic, unpleasant taste, hoarseness or nasal congestion, pain or headache and visual changes. Allergic reactions rarely may occur.

Nasal corticosteroids may be associated with central serous retinopathy.[4]

Footnotes

  1. ^ Willey R, Milne L, Crompton G, Grant I (1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis". Br J Dis Chest 70 (1): 32–8. doi:10.1016/0007-0971(76)90004-8. PMID 1259918.  
  2. ^ Salzman G, Pyszczynski D (1988). "Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber". J Allergy Clin Immunol 81 (2): 424–8. doi:10.1016/0091-6749(88)90911-6. PMID 3339197.  
  3. ^ Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S (2003). "Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone". Ann Allergy Asthma Immunol 90 (6): 646–51. PMID 12839324.  
  4. ^ Haimovici R, Gragoudas ES, Duker JS, Sjaarda RN, Eliott D (October 1997). "Central serous chorioretinopathy associated with inhaled or intranasal corticosteroids". Ophthalmology 104 (10): 1653–60. PMID 9331207.  
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