Beclometasone

Beclometasone

Clinical data
Trade names	Qvar, Beconase AQ, others
Other names	Beclomethasone (USAN); Beclometasone dipropionate; Beclomethasone dipropionate
AHFS/Drugs.com	Monograph
MedlinePlus	a681047
License data	US DailyMed: Beclomethasone US FDA: Beclomethasone
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 medicine) 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
Elimination 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
KEGG	D00689
ChEBI	CHEBI:3002 Y
ChEMBL	ChEMBL1200500 N
CompTox Dashboard (EPA)	DTXSID3048730
ECHA InfoCard	100.024.442
Chemical and physical data
Formula	C28H37ClO7
Molar mass	521.05 g·mol−1
3D model (JSmol)	Interactive image
Melting point	117 to 120 °C (243 to 248 °F) (dec.)
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?)  (verify)

Beclometasone or beclomethasone, also known as 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.

Beclomethasone 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. In 2020, it was the 220th most commonly prescribed medication in the United States, with more than 2 million prescriptions.

Side effects

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.

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.

Pharmacology

Beclometasone is mainly a glucocorticoid. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor that is present in almost every vertebrate animal cell. The activated glucocorticoid receptor-glucocorticoid complex up-regulates the expression of anti-inflammatory proteins in the nucleus (a process known as transactivation) and represses the expression of proinflammatory proteins in the cytosol by preventing the translocation of other transcription factors from the cytosol into the nucleus (transrepression).

Glucocorticoids are part of the feedback mechanism in the immune system which reduces certain aspects of immune function, such as inflammation.

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). The prodrug beclometasone is marketed in Norway and Russia.

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

External links

• "Beclometasone". Drug Information Portal. U.S. National Library of Medicine.