Beclometasone dipropionate

Beclometasone dipropionate

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 Y
ATC code	A07EA07 D07AC15, R01AD01, R03BA01
PubChem	CID 21700
DrugBank	APRD00564
ChemSpider	20396 Y
UNII	5B307S63B2 Y
ChEBI	CHEBI:3002 Y
ChEMBL	CHEMBL1200500 N
Chemical data
Formula	C28H37ClO7
Mol. mass	521.042 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 Y Key:KUVIULQEHSCUHY-XYWKZLDCSA-N Y
N(what is this?)  dipropionate (verify)

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. 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), 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 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.

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 similar 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]

See also

• Epinephrine
• Ipratropium
• Salbutamol

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. doi:10.1016/S1081-1206(10)61870-4. 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.