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Beclometasone

From Wikipedia, the free encyclopedia
(Redirected fromBeclometasone dipropionate)
Chemical compound

Pharmaceutical compound
Beclometasone
Clinical data
Trade namesVanceril, others
Other namesBeclometasone dipropionate; beclomethasone dipropionate, beclomethasone (USANUS)
AHFS/Drugs.comMonograph
MedlinePlusa681047
License data
Pregnancy
category
Routes of
administration
Inhalation,nasal,topical
ATC code
Legal status
Legal status
Identifiers
  • (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
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.024.442Edit this at Wikidata
Chemical and physical data
FormulaC22H29ClO5
Molar mass408.92 g·mol−1
3D model (JSmol)
Melting point117 to 120 °C (243 to 248 °F) (dec.)
  • O=C1C=CC2(C(=C1)CCC3C4CC(C)C(O)(C(=O)CO)C4(C)CC(O)C32Cl)C

  • 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=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
  • Key:NBMKJKDGKREAPL-DVTGEIKXSA-N

  • 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
  • Key:KUVIULQEHSCUHY-XYWKZLDCSA-N

Beclometasone orbeclomethasone, sold under the brand nameVanceril among others, is asteroid medication.[5] It is available as aninhaler, cream, pills, andnasal spray.[6] The inhaled form is used in the long-term management ofasthma.[5] The cream may be used fordermatitis andpsoriasis.[7] The pills have been used to treatulcerative colitis.[8] The nasal spray is used to treatallergic rhinitis andnasal polyps.[9]

Common side effects with the inhaled form includerespiratory infections, headaches, and throat inflammation.[5] Serious side effects include an increased risk of infection,cataracts,Cushing's syndrome, andsevere allergic reactions.[5] Long-term use of the pill form may causeadrenal insufficiency.[8] The pills may also cause mood or personality changes.[8] The inhaled form is generally regarded as safe inpregnancy.[10] Beclometasone is aglucocorticoid.[5]

Beclomethasone, as beclomethasone dipropionate, was first patented in 1962 and used medically in 1972.[11] It was approved for medical use in the United States in 1976.[5] It is a therapeutic alternative on theWorld Health Organization's List of Essential Medicines.[12] In 2023, it was the 351st most commonly prescribed medication in the United States, with more than 51,000 prescriptions.[13]

Medical uses

[edit]

Beclometasone isindicated for maintenance treatment of asthma as prophylactic therapy;[2] for the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis;[3] and the relief of the symptoms of seasonal or perennial allergic and nonallergic (vasomotor) rhinitis.[4]

Side effects

[edit]

Common side effects with the inhaled form includerespiratory infections, headaches, and throat inflammation.[5] Serious side effects include an increased risk of infection,cataracts,Cushing's syndrome, andsevere allergic reactions.[5] Long-term use of the pill form may causeadrenal insufficiency.[8] The pills may also cause mood or personality changes.[8] The inhaled form is generally regarded as safe inpregnancy.[10]

Occasionally, it may cause acough upon inhalation. Deposition on thetongue andthroat may promote oralcandidiasis, which appears as a white coating, possibly with irritation.[14][15][16]

Nasal corticosteroids may be associated withcentral serous retinopathy.[17]

Pharmacology

[edit]
Main article:Glucocorticoid § Pharmacology

Beclometasone is aglucocorticoid.[5] Glucocorticoids are corticosteroids that bind to theglucocorticoid receptor[18] that is present in almost everyvertebrate animal cell. The activated glucocorticoid receptor-glucocorticoid complex up-regulates the expression of anti-inflammatory proteins in thenucleus (a process known astransactivation) and represses the expression of proinflammatory proteins in thecytosol by preventing thetranslocation of othertranscription factors from the cytosol into the nucleus (transrepression).[19]

Society and culture

[edit]

Names

[edit]

Beclometasone dipropionate is theinternational nonproprietary name modified and beclomethasone dipropionate is theUnited States Adopted Name and formerBritish Approved Name. It is aprodrug of the free form, beclometasone (INN). The prodrug beclometasone is marketed in Norway and Russia.[20][21][22][23][24]

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

References

[edit]
  1. ^"Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025"(pdf).Therapeutic Goods Administration (TGA). May 2025. Retrieved31 August 2025.
  2. ^ab"Qvar Redihaler- beclomethasone dipropionate hfa aerosol, metered".DailyMed. 20 August 2025. Retrieved1 September 2025.
  3. ^ab"Qnasl- beclomethasone dipropionate aerosol, metered; Qnasl- beclomethasone dipropionate aerosol, metered".DailyMed. 27 September 2022. Retrieved5 September 2025.
  4. ^ab"Beconase- beclomethasone dipropionate monohydrate spray, suspension".DailyMed. 8 September 2010. Retrieved5 September 2025.
  5. ^abcdefghi"Beclomethasone Dipropionate". The American Society of Health-System Pharmacists.Archived from the original on 8 December 2015. Retrieved2 December 2015.
  6. ^"List of products: Beclometasone dipropionate".MHRA.Archived from the original on 8 December 2015. Retrieved6 December 2015.
  7. ^"Beclometasone dipropionate 0.25 mg/g Cream"(PDF).MHRA. Archived fromthe original(PDF) on 8 December 2015. Retrieved6 December 2015.
  8. ^abcde"Clipper"(PDF).MHRA. Archived fromthe original(PDF) on 8 December 2015. Retrieved6 December 2015.
  9. ^"Beclomethasone Dipropionate eent". The American Society of Health-System Pharmacists.Archived from the original on 8 December 2015. Retrieved2 December 2015.
  10. ^abHamilton R (2015).Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 349.ISBN 9781284057560.
  11. ^McPherson EM (2007)."Beclomethasone dipropionate".Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 539.ISBN 9780815518563.Archived from the original on 8 December 2015.
  12. ^World Health Organization (2025).The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization.hdl:10665/382243.
  13. ^"Beclomethasone Drug Usage Statistics, United States, 2014 - 2023".ClinCalc. Retrieved17 August 2025.
  14. ^Willey RF, Milne LJ, Crompton GK, Grant IW (January 1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis".British Journal of Diseases of the Chest.70 (1):32–38.doi:10.1016/0007-0971(76)90004-8.PMID 1259918.
  15. ^Salzman GA, Pyszczynski DR (February 1988)."Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber".The Journal of Allergy and Clinical Immunology.81 (2):424–428.doi:10.1016/0091-6749(88)90911-6.PMID 3339197.
  16. ^Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, et al. (June 2003). "Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone".Annals of Allergy, Asthma & Immunology.90 (6):646–651.doi:10.1016/S1081-1206(10)61870-4.PMID 12839324.
  17. ^Haimovici R, Gragoudas ES, Duker JS, Sjaarda RN, Eliott D (October 1997)."Central serous chorioretinopathy associated with inhaled or intranasal corticosteroids".Ophthalmology.104 (10):1653–1660.doi:10.1016/s0161-6420(97)30082-7.PMID 9331207.
  18. ^Pelt AC (2011).Glucocorticoids: effects, action mechanisms, and therapeutic uses. Hauppauge, N.Y.: Nova Science.ISBN 978-1617287589.
  19. ^Rhen T, Cidlowski JA (October 2005). "Antiinflammatory action of glucocorticoids--new mechanisms for old drugs".The New England Journal of Medicine.353 (16):1711–1723.doi:10.1056/NEJMra050541.PMID 16236742.S2CID 5744727.
  20. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 123–.ISBN 978-1-4757-2085-3.
  21. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 95–.ISBN 978-3-88763-075-1.
  22. ^Morton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 46–.ISBN 978-94-011-4439-1.Archived from the original on 12 January 2023. Retrieved17 March 2019.
  23. ^Muller NF, Dessing RP, eds. (19 June 1998).European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 141–.ISBN 978-3-7692-2114-5.Archived from the original on 12 January 2023. Retrieved17 March 2019.
  24. ^"Beclometasone".drugs.com.Archived from the original on 18 January 2018. Retrieved17 March 2019.
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