View source for Chemistry:Beclometasone dipropionate

{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 459526640
| drug_name =
| IUPAC_name = (8''S'',9''R'',10''S'',11''S'',13''S'',14''S'',16''S'',17''R'')-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
| image = Beclometasone dipropionate.png
| width = 240
| image2 = Beclometasone-dipropionate-3D-balls.png
| width2 = 250
<!--Clinical data-->
| tradename =  Qvar, Beconase AQ, others
| Drugs.com = {{drugs.com|monograph|beclomethasone-dipropionate-eent}}
| MedlinePlus = a681047
| pregnancy_AU = B3
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_AU = S2
| legal_CA = <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = POM
| legal_UK_comment = but some nasal sprays are General sales list (GSL, OTC)
| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
| routes_of_administration = inhalation, nasal, topical
<!--Pharmacokinetic data-->
| bioavailability = Converted to beclometasone-17-monopropionate (17-BMP) during absorption
| protein_bound = 87% of 17-BMP to albumin and transcortin
| metabolism = By [[Biology:Esterase|esterase]] enzymes found in most tissues
| elimination_half-life = 2.8 hours
| excretion = Biliary (60%), renal (12%)
<!--Identifiers-->
| IUPHAR_ligand = 5894
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 5534-09-8
| ATC_prefix = A07
| ATC_suffix = EA07
| ATC_supplemental =  {{ATC|D07|AC15}}, {{ATC|R01|AD01}}, {{ATC|R03|BA01}}
| PubChem = 21700
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00394
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20396
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5B307S63B2
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3002
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200500
<!--Chemical data-->
| C=28  
| H=37
| Cl=1  
| O=7
| molecular_weight = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KUVIULQEHSCUHY-XYWKZLDCSA-N
}}
<!-- Definition and medical uses -->
'''Beclometasone dipropionate''', also spelled '''beclomethasone dipropionate''' and sold under the brand name '''Qvar''' among others, is a [[Biology:Corticosteroid|steroid medication]].<ref name=AHFS2015>{{cite web|title=Beclomethasone Dipropionate|url=https://www.drugs.com/monograph/beclomethasone-dipropionate.html|publisher=The American Society of Health-System Pharmacists|accessdate=Dec 2, 2015|deadurl=no|archiveurl=https://web.archive.org/web/20151208145637/http://www.drugs.com/monograph/beclomethasone-dipropionate.html|archivedate=2015-12-08|df=}}</ref> It is available as an [[Engineering:Inhaler|inhaler]], cream, pills, and [[Medicine:Nasal spray|nasal spray]].<ref name=MHRA2015>{{cite web|title=List of products: BECLOMETASONE DIPROPIONATE|url=http://www.mhra.gov.uk/spc-pil/?subsName=BECLOMETASONE%20DIPROPIONATE&pageID=SecondLevel|website=MHRA|accessdate=6 December 2015|deadurl=no|archiveurl=https://web.archive.org/web/20151208113019/http://www.mhra.gov.uk/spc-pil/?subsName=BECLOMETASONE%20DIPROPIONATE&pageID=SecondLevel|archivedate=8 December 2015|df=}}</ref> The inhaled form is used in the long-term management of [[Medicine:Asthma|asthma]].<ref name=AHFS2015/> The cream may be used for [[Medicine:Dermatitis|dermatitis]] and [[Medicine:Psoriasis|psoriasis]].<ref>{{cite web|title=Beclometasone dipropionate 0.25 mg/g Cream|url=http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1444971110586.pdf|website=MHRA|accessdate=6 December 2015|deadurl=no|archiveurl=https://web.archive.org/web/20151208111605/http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1444971110586.pdf|archivedate=8 December 2015|df=}}</ref> The pills have been used to treat [[Medicine:Ulcerative colitis|ulcerative colitis]].<ref name=MHRA2015Pill>{{cite web|title=Clipper|url=http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1353302219931.pdf|website=MHRA|accessdate=6 December 2015|deadurl=no|archiveurl=https://web.archive.org/web/20151208154434/http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1353302219931.pdf|archivedate=8 December 2015|df=}}</ref> The nasal spray is used to treat [[Medicine:Allergic rhinitis|allergic rhinitis]] and [[Medicine:Nasal polyp|nasal polyp]]s.<ref name=AHFS2015ENT>{{cite web|title=Beclomethasone Dipropionate eent|url=https://www.drugs.com/monograph/beclomethasone-dipropionate-eent.html|publisher=The American Society of Health-System Pharmacists|accessdate=Dec 2, 2015|deadurl=no|archiveurl=https://web.archive.org/web/20151208200147/http://www.drugs.com/monograph/beclomethasone-dipropionate-eent.html|archivedate=2015-12-08|df=}}</ref>

<!-- Side effects and mechanism -->
Common side effects with the inhaled form include [[Medicine:Respiratory tract infection|respiratory infections]], headaches, and throat inflammation.<ref name=AHFS2015/> Serious side effects include an increased risk of infection, cataracts, Cushing’s syndrome, and [[Medicine:Anaphylaxis|severe allergic reactions]].<ref name=AHFS2015/> Long-term use of the pill form may cause adrenal insufficiency.<ref name=MHRA2015Pill/> The pills may also cause mood or personality changes.<ref name=MHRA2015Pill/> The inhaled form is generally regarded as safe in [[Medicine:Pregnancy|pregnancy]].<ref name=Ric2015a>{{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=349}}</ref> Beclometasone is mainly a [[Chemistry:Glucocorticoid|glucocorticoid]].<ref name=AHFS2015/>

<!-- Society and culture -->
Beclometasone dipropionate was first patented in 1962 and used medically in 1972.<ref>{{cite book|last1=McPherson|first1=Edwin M.|title=Pharmaceutical Manufacturing Encyclopedia.|date=2007|publisher=Elsevier|location=Burlington|isbn=9780815518563|page=539|edition=3rd|url=https://books.google.ca/books?id=_J2ti4EkYpkC&pg=PA539|deadurl=no|archiveurl=https://web.archive.org/web/20151208065619/https://books.google.ca/books?id=_J2ti4EkYpkC&pg=PA539|archivedate=2015-12-08|df=}}</ref> It was approved for medical use in the United States in 1976.<ref name=AHFS2015/> It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a [[Medicine:Health system|health system]].<ref name=WHO19th>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}}</ref> The wholesale price in the developing world for an inhaler containing 200 doses of medication is about 3.20 USD as of 2014.<ref>{{cite web|title=Beclometasone|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=1004&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=6 December 2015}}</ref> In the United States it costs between 50 and 100 USD for a typical month supply of the inhaled form.<ref name=Ric2015b>{{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=451}}</ref>

==Side effects==
Occasionally, it may cause a cough upon inhalation. Deposition on the [[Biology:Tongue|tongue]] and [[Medicine:Throat|throat]] may promote oral [[Medicine:Candidiasis|candidiasis]], which appears as a white coating, possibly with irritation.<!--
  --><ref>{{cite journal |vauthors=Willey R, Milne L, Crompton G, Grant I | title=Beclomethasone dipropionate aerosol and oropharyngeal candidiasis | journal=Br J Dis Chest | volume=70 | issue=1 | pages=32–8 | year=1976 | pmid=1259918 | doi=10.1016/0007-0971(76)90004-8}}</ref><!--
  --><ref>{{cite journal |vauthors=Salzman G, Pyszczynski D | title=Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber | journal=J Allergy Clin Immunol | volume=81 | issue=2 | pages=424–8 | year=1988 | pmid=3339197 | doi=10.1016/0091-6749(88)90911-6}}</ref><!--
  --><ref>{{cite journal | doi=10.1016/S1081-1206(10)61870-4 |vauthors=Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S | title=Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone | journal=Ann Allergy Asthma Immunol | volume=90 | issue=6 | pages=646–51 | year=2003 | pmid=12839324}}</ref>
This may usually be prevented by rinsing the mouth with water after using the inhaler. Other [[Medicine:Adverse drug reaction|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. [[Medicine:Allergy|Allergic]] reactions may occur, but rarely.

Nasal corticosteroids may be associated with [[Medicine:Central serous retinopathy|central serous retinopathy]].<ref>{{cite journal |vauthors=Haimovici R, Gragoudas ES, Duker JS, Sjaarda RN, Eliott D |title=Central serous chorioretinopathy associated with inhaled or intranasal corticosteroids |journal=Ophthalmology |volume=104 |issue=10 |pages=1653–60 |date=October 1997 |pmid=9331207 |doi=10.1016/s0161-6420(97)30082-7}}</ref>

==Names==
Beclometasone dipropionate is the INN modified and beclomethasone dipropionate is the USAN and former [[Chemistry:British Approved Name|BAN]]. It is a [[Chemistry:Prodrug|prodrug]] of the free form, beclometasone (INN).

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

==References==
{{Reflist|32em}}

{{Glucocorticoids}}
{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}
{{Nasal preparations}}
{{Asthma and copd rx}}
{{Glucocorticoidics}}

[[Category:Corticosteroid esters]]
[[Category:Glucocorticoids]]
[[Category:Propionates]]
[[Category:Organochlorides]]
[[Category:World Health Organization essential medicines]]


{{Sourceattribution|Beclometasone dipropionate|1}}