Beclometasone dipropionate

Beclometasone dipropionate (INN modified)

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
Trade names	Qvar, Beconase AQ, others
AHFS/Drugs.com	monograph
MedlinePlus	a681047
Pregnancy category	AU: B3
Legal status	AU: S2 (Pharmacy only) UK: Prescription-only (POM), but some nasal sprays are General sales list (GSL, OTC)
Routes of administration	Oral inhalation, 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
Biological half-life	2.8 hours
Excretion	Biliary (60%), renal (12%)
Identifiers
CAS Number	5534-09-8 Y
ATC code	A07EA07 (WHO) D07AC15, R01AD01, R03BA01
PubChem	CID: 21700
IUPHAR/BPS	5894
DrugBank	DB00394 N
ChemSpider	20396 Y
UNII	5B307S63B2 Y
ChEBI	CHEBI:3002 Y
ChEMBL	CHEMBL1200500 N
Chemical data
Formula	C28H37ClO7
Molecular mass	521.042 g/mol
SMILES O=C(OCC(=O)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(Cl)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C)CC
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
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Beclometasone dipropionate, also spelled beclomethasone dipropionate and sold under the brand name Qvar among others, is a steroid medication. It is available as an inhaler, cream, pills, and nasal spray. The inhaled form is used in the long term management of asthma. The cream may be used for dermatitis and psoriasis. The pills have been used to treat ulcerative colitis. The nasal spray is used to treat allergic rhinitis and nasal polyps.

Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation. Serious side effects include an increased risk of infection, cataracts, Cushing’s syndrome, and severe allergic reactions. Long term use of the pill form may cause adrenal insufficiency. The pills may also cause mood or personality changes. The inhaled form is generally regarded as safe in pregnancy. Beclometasone is mainly a glucocorticoid.

Beclometasone dipropionate was first patented in 1962 and used medically in 1972. It was approved for medical use in the United States in 1976. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. The wholesale price for an inhaler containing 200 doses of medication is about 3.20 USD as of 2014. In the United States it costs between 50 and 100 USD for a typical month supply of the inhaled form.

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. This may usually be prevented by rinsing the mouth with water after using the inhaler. Other adverse drug reaction 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 may occur, but rarely.

Nasal corticosteroids may be associated with central serous retinopathy.

Names

Beclometasone dipropionate is the INN modified and beclomethasone dipropionate is the USAN and former BAN. It is a prodrug of the free form, beclometasone (INN).

Clenil, Qvar are brandnames for the inhalers. Beconase, alanase, Vancenase, Qnasl for the nasal spray or aerosol.