Beclometasone

{{Short description|Chemical compound}} {{Use dmy dates|date=January 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Infobox drug | image = Beclometasone dipropionate.png | image_class = skin-invert-image | width = 240 | alt = | image2 = Beclometasone-dipropionate-3D-balls.png | image_class2 = bg-transparent | width2 = 250 | alt2 = | USAN = beclomethasone

| pronounce = | tradename = Vanceril, others | Drugs.com = {{drugs.com|monograph|beclomethasone-dipropionate-eent}} | MedlinePlus = a681047 | DailyMedID = Beclomethasone | pregnancy_AU = B3 | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Inhalation, nasal, topical | class = | ATC_prefix = A07 | ATC_suffix = EA07 | ATC_supplemental = {{ATC|D07|AC15}}, {{ATC|R01|AD01}}, {{ATC|R03|BA01}}

| legal_AU = S2 | legal_AU_comment = /{{nbsp}}Schedule 4<ref>{{cite web | title=Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025 | website=Therapeutic Goods Administration (TGA) | date=May 2025 | url=https://www.legislation.gov.au/F2025L00599/asmade/2025-05-28/text/original/pdf | format=pdf | access-date=31 August 2025}}</ref> | legal_BR =  | legal_BR_comment = | legal_CA =  | legal_CA_comment = | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = <ref name="Qvar Redihaler FDA label">{{cite web | title=Qvar Redihaler- beclomethasone dipropionate hfa aerosol, metered | website=DailyMed | date=20 August 2025 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cada897a-264e-450d-ae00-36e7fe747080 | access-date=1 September 2025}}</ref><ref name="Qnasl FDA label">{{cite web | title=Qnasl- beclomethasone dipropionate aerosol, metered; Qnasl- beclomethasone dipropionate aerosol, metered | website=DailyMed | date=27 September 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4b8d8e84-b5d2-4e56-97ec-4f72971465c5 | access-date=5 September 2025}}</ref><ref name="Beconase FDA label">{{cite web | title=Beconase- beclomethasone dipropionate monohydrate spray, suspension | website=DailyMed | date=8 September 2010 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6e8f7981-f2ca-4b56-8759-4f18cf9706c8 | access-date=5 September 2025}}</ref> | legal_EU = | legal_EU_comment = | legal_UN =  | legal_UN_comment = | legal_status =

| IUPAC_name = (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one | C=22 | H=29 | Cl=1 | O=5 | SMILES = O=C1C=CC2(C(=C1)CCC3C4CC(C)C(O)(C(=O)CO)C4(C)CC(O)C32Cl)C | SMILES2 = 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 = 1S/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1 | StdInChI2 = 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 = NBMKJKDGKREAPL-DVTGEIKXSA-N | StdInChIKey2 = KUVIULQEHSCUHY-XYWKZLDCSA-N | density = | density_notes = | melting_point = 117 | melting_high = 120 | melting_notes = (dec.) | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

'''Beclometasone''' or '''beclomethasone''', sold under the brand name '''Vanceril''' among others, is a 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|access-date=2 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151208145637/http://www.drugs.com/monograph/beclomethasone-dipropionate.html|archive-date=8 December 2015}}</ref> It is available as an inhaler, cream, pills, and 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|access-date=6 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151208113019/http://www.mhra.gov.uk/spc-pil/?subsName=BECLOMETASONE%20DIPROPIONATE&pageID=SecondLevel|archive-date=8 December 2015}}</ref> The inhaled form is used in the long-term management of asthma.<ref name=AHFS2015/> The cream may be used for dermatitis and 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|access-date=6 December 2015|url-status=dead|archive-url=https://web.archive.org/web/20151208111605/http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1444971110586.pdf|archive-date=8 December 2015}}</ref> The pills have been used to treat ulcerative colitis.<ref name=MHRA2015Pill>{{cite web|title=Clipper|url=http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1353302219931.pdf|website=MHRA|access-date=6 December 2015|url-status=dead|archive-url=https://web.archive.org/web/20151208154434/http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1353302219931.pdf|archive-date=8 December 2015}}</ref> The nasal spray is used to treat allergic rhinitis and nasal polyps.<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|access-date=2 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151208200147/http://www.drugs.com/monograph/beclomethasone-dipropionate-eent.html|archive-date=8 December 2015}}</ref>

Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation.<ref name=AHFS2015/> Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and 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 pregnancy.<ref name=Ric2015a>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=349}}</ref> Beclometasone is a glucocorticoid.<ref name=AHFS2015/>

Beclomethasone, as beclomethasone dipropionate, was first patented in 1962 and used medically in 1972.<ref>{{cite book| vauthors = McPherson EM | chapter = Beclomethasone dipropionate |title=Pharmaceutical Manufacturing Encyclopedia. |date=2007 |publisher=Elsevier |location=Burlington |isbn=9780815518563|page=539|edition=3rd| chapter-url = https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA539|url-status=live|archive-url= https://web.archive.org/web/20151208065619/https://books.google.ca/books?id=_J2ti4EkYpkC&pg=PA539|archive-date=8 December 2015}}</ref> It was approved for medical use in the United States in 1976.<ref name=AHFS2015/> It is a therapeutic alternative on the World Health Organization's List of Essential Medicines.<ref name="WHO24th">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list | year = 2025 | hdl = 10665/382243 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl-access=free }}</ref> In 2023, it was the 351st most commonly prescribed medication in the United States, with more than 51,000 prescriptions.<ref>{{cite web | title = Beclomethasone Drug Usage Statistics, United States, 2014 - 2023 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Beclomethasone | access-date = 17 August 2025}}</ref>

== Medical uses == Beclometasone is indicated for maintenance treatment of asthma as prophylactic therapy;<ref name="Qvar Redihaler FDA label" /> for the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis;<ref name="Qnasl FDA label" /> and the relief of the symptoms of seasonal or perennial allergic and nonallergic (vasomotor) rhinitis.<ref name="Beconase FDA label" />

==Side effects== Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation.<ref name=AHFS2015/> Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and 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 pregnancy.<ref name=Ric2015a/>

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.<ref>{{cite journal | vauthors = Willey RF, Milne LJ, Crompton GK, Grant IW | title = Beclomethasone dipropionate aerosol and oropharyngeal candidiasis | journal = British Journal of Diseases of the Chest | volume = 70 | issue = 1 | pages = 32–38 | date = January 1976 | pmid = 1259918 | doi = 10.1016/0007-0971(76)90004-8 }}</ref><ref>{{cite journal | vauthors = Salzman GA, Pyszczynski DR | title = Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber | journal = The Journal of Allergy and Clinical Immunology | volume = 81 | issue = 2 | pages = 424–428 | date = February 1988 | pmid = 3339197 | doi = 10.1016/0091-6749(88)90911-6 | doi-access = free }}</ref><ref>{{cite journal | 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 = Annals of Allergy, Asthma & Immunology | volume = 90 | issue = 6 | pages = 646–651 | date = June 2003 | pmid = 12839324 | doi = 10.1016/S1081-1206(10)61870-4 }}</ref>

Nasal corticosteroids may be associated with 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 = 1653–1660 | date = October 1997 | pmid = 9331207 | doi = 10.1016/s0161-6420(97)30082-7 | doi-access = free }}</ref>

==Pharmacology== {{main|Glucocorticoid#Pharmacology}} Beclometasone is a glucocorticoid.<ref name=AHFS2015/> Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor<ref name = "Pelt_2011">{{cite book | vauthors = Pelt AC | title = Glucocorticoids: effects, action mechanisms, and therapeutic uses | year = 2011 | publisher = Nova Science | location = Hauppauge, N.Y. | isbn = 978-1617287589 }}</ref> 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).<ref name="RhenNEJM">{{cite journal | vauthors = Rhen T, Cidlowski JA | title = Antiinflammatory action of glucocorticoids--new mechanisms for old drugs | journal = The New England Journal of Medicine | volume = 353 | issue = 16 | pages = 1711–1723 | date = October 2005 | pmid = 16236742 | doi = 10.1056/NEJMra050541 | s2cid = 5744727 }}</ref>

== Society and culture == === Names === Beclometasone dipropionate is the international nonproprietary name modified and beclomethasone dipropionate is the United States Adopted Name and former British Approved Name. It is a prodrug of the free form, beclometasone (INN). The prodrug beclometasone is marketed in Norway and Russia.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA123|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=123–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA95|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=95–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA46|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=46–|access-date=17 March 2019|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112040416/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA46|url-status=live}}</ref><ref name="Muller1998">{{cite book| veditors = Muller NF, Dessing RP|title=European Drug Index: European Drug Registrations | edition = Fourth |url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA141 |date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=141–|access-date=17 March 2019|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112040422/https://books.google.com/books?id=2HBPHmclMWIC&pg=PA141|url-status=live}}</ref><ref name="Drugs.com">{{cite web |url=https://www.drugs.com/international/beclometasone.html |website=drugs.com |title=Beclometasone |access-date=17 March 2019 |archive-date=18 January 2018 |archive-url=https://web.archive.org/web/20180118064657/https://www.drugs.com/international/beclometasone.html |url-status=live }}</ref>

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

== References == {{Reflist}}

{{Glucocorticoids}} {{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} {{Nasal preparations}} {{Asthma and copd rx}} {{Glucocorticoidics}} {{GlaxoSmithKline}} {{Portal bar | Medicine}} {{Authority control}}

Category:Anti-asthmatic agents Category:Corticosteroid esters Category:Drugs developed by GSK plc Category:Glucocorticoids Category:Organochlorides Category:Propionate esters Category:World Health Organization essential medicines Category:Wikipedia medicine articles ready to translate