View source for Beclometasone

{{Short description|Chemical compound}}
{{Use dmy dates|date=January 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 459526640
| image = Beclometasone dipropionate.png
| image_class = skin-invert-image
| width = 240
| image2 = Beclometasone-dipropionate-3D-balls.png
| width2 = 250
| USAN = beclomethasone

<!-- Clinical data -->
| tradename =  Qvar, Beconase AQ, others
| Drugs.com = {{drugs.com|monograph|beclomethasone-dipropionate-eent}}
| MedlinePlus = a681047
| DailyMedID = Beclomethasone
| pregnancy_AU = B3
| pregnancy_category =  
| routes_of_administration = Inhalation, nasal, topical

| 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 = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = Converted to beclometasone-17-monopropionate (17-BMP) during absorption
| protein_bound = 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 -->
| 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
| KEGG = D00689
| 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
| synonyms  = Beclometasone dipropionate; beclomethasone dipropionate

<!-- Chemical data -->
| 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
| C=28  | H=37| Cl=1  | O=7
| 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
| melting_point = 117
| melting_high = 120
| melting_notes = (dec.)
}}

<!-- Definition and medical uses -->
'''Beclometasone''' or '''beclomethasone''', also known as '''beclomethasone dipropionate''', and sold under the brand name '''Qvar''' among others, is a [[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|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 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 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 [[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 [[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 mainly a [[glucocorticoid]].<ref name=AHFS2015/>

<!-- Society and culture -->
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 on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In 2021, it was the 268th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Beclomethasone - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Beclomethasone | access-date = 14 January 2024}}</ref>

==Side effects==
Common side effects with the inhaled form include [[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 [[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 [[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>
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, [[Dysphonia|hoarseness]] or [[nasal congestion]], pain or headache, and visual changes. [[Allergy|Allergic]] reactions may occur, but rarely.

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 mainly 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 [[cell nucleus|nucleus]] (a process known as [[transactivation]]) and represses the expression of proinflammatory proteins in the [[cytosol]] by preventing the [[protein targeting|translocation]] of other [[transcription factor]]s 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>

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 [[International Nonproprietary Name|INN]] modified and beclomethasone dipropionate is the [[United States Adopted Name|USAN]] and former [[British Approved Name|BAN]]. 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 brandnames 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:Antiasthmatic drugs]]
[[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]]