Beclometasone dipropionate

Beclometasone dipropionate

Clinical data
Trade names	Qvar, Beconase AQ, others
AHFS/Drugs.com	Monograph
MedlinePlus	a681047
Pregnancy category	AU: B3
Routes of administration	inhalation, nasal, topical
ATC code	A07EA07 (WHO) D07AC15 (WHO), R01AD01 (WHO), R03BA01 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) UK: POM (Prescription only) but some nasal sprays are General sales list (GSL, OTC)
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
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
CAS Number	5534-09-8 Y
PubChem CID	21700
IUPHAR/BPS	5894
DrugBank	DB00394 N
ChemSpider	20396 Y
UNII	5B307S63B2
ChEBI	CHEBI:3002 Y
ChEMBL	CHEMBL1200500 N
ECHA InfoCard	100.024.442
Chemical and physical data
Formula	C28H37ClO7
Molar mass	521.042 g/mol
3D model (Jmol)	Interactive image
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
NY (what is this?)

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 effective and safe medicines needed in a health system. The wholesale price in the developing world 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.