# Beclometasone

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> Markdown URL: https://mediated.wiki/source/Beclometasone.md
> Source: https://en.wikipedia.org/wiki/Beclometasone
> Source revision: 1356873517
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{{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

<!-- Clinical data -->
| 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](/source/Inhalation_administration), [nasal](/source/Nasal_administration), [topical](/source/Topical_medication)
| class = 
| ATC_prefix = A07
| ATC_suffix = EA07
| ATC_supplemental = {{ATC|D07|AC15}}, {{ATC|R01|AD01}}, {{ATC|R03|BA01}}

<!-- Legal status -->
| 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 = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C5, D1, D2, E, F1, F2, F3, F4 -->
| legal_BR_comment = 
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| 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 = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 
| excretion =

<!-- Identifiers -->
| index2_label = dipropionate
| CAS_number = 4419-39-0
| CAS_number2 = 5534-09-8
| PubChem = 20469
| PubChem2 = 21700
| IUPHAR_ligand = 5894
| DrugBank2 = DB00394
| ChemSpiderID = 20396
| UNII = KGZ1SLC28Z
| UNII2 = 5B307S63B2
| KEGG = D07495
| KEGG2 = D00689
| ChEBI = 3002
| ChEMBL = 1200500
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = Beclometasone dipropionate; beclomethasone dipropionate

<!-- Chemical and physical data -->
| 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 = 
}}

<!-- Definition and medical uses -->
'''Beclometasone''' or '''beclomethasone''', sold under the brand name '''Vanceril''' among others, is a [steroid medication](/source/corticosteroid).<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](/source/inhaler), cream, pills, and [nasal spray](/source/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](/source/asthma).<ref name=AHFS2015/> The cream may be used for [dermatitis](/source/dermatitis) and [psoriasis](/source/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](/source/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](/source/allergic_rhinitis) and [nasal polyp](/source/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|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>

<!-- Side effects and mechanism -->
Common side effects with the inhaled form include [respiratory infections](/source/Respiratory_tract_infection), headaches, and throat inflammation.<ref name=AHFS2015/> Serious side effects include an increased risk of infection, [cataracts](/source/cataracts), [Cushing's syndrome](/source/Cushing's_syndrome), and [severe allergic reactions](/source/anaphylaxis).<ref name=AHFS2015/> Long-term use of the pill form may cause [adrenal insufficiency](/source/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](/source/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](/source/glucocorticoid).<ref name=AHFS2015/>

<!-- Society and culture -->
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](/source/WHO_Model_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](/source/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](/source/Respiratory_tract_infection), headaches, and throat inflammation.<ref name=AHFS2015/> Serious side effects include an increased risk of infection, [cataracts](/source/cataracts), [Cushing's syndrome](/source/Cushing's_syndrome), and [severe allergic reactions](/source/anaphylaxis).<ref name=AHFS2015/> Long-term use of the pill form may cause [adrenal insufficiency](/source/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](/source/pregnancy).<ref name=Ric2015a/>

Occasionally, it may cause a [cough](/source/cough) upon inhalation. Deposition on the [tongue](/source/tongue) and [throat](/source/throat) may promote oral [candidiasis](/source/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](/source/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](/source/glucocorticoid).<ref name=AHFS2015/> Glucocorticoids are corticosteroids that bind to the [glucocorticoid receptor](/source/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](/source/vertebrate) animal cell. The activated glucocorticoid receptor-glucocorticoid complex up-regulates the expression of anti-inflammatory proteins in the [nucleus](/source/cell_nucleus) (a process known as [transactivation](/source/transactivation)) and represses the expression of proinflammatory proteins in the [cytosol](/source/cytosol) by preventing the [translocation](/source/protein_targeting) of other [transcription factor](/source/transcription_factor)s from the cytosol into the nucleus ([transrepression](/source/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](/source/international_nonproprietary_name) modified and beclomethasone dipropionate is the [United States Adopted Name](/source/United_States_Adopted_Name) and former [British Approved Name](/source/British_Approved_Name). It is a [prodrug](/source/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}}
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{{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

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Adapted from the Wikipedia article [Beclometasone](https://en.wikipedia.org/wiki/Beclometasone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Beclometasone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.