Beclometasone

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Beclometasone
Beclometasone dipropionate.png
Beclometasone-dipropionate-3D-balls.png
Clinical data
Trade names Vanceril, others
Other namesBeclometasone dipropionate; beclomethasone dipropionate, beclomethasone (USAN US)
AHFS/Drugs.com Monograph
MedlinePlus a681047
License data
Pregnancy
category
  • AU:B3
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.024.442 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H29ClO5
Molar mass 408.92 g·mol−1
3D model (JSmol)
Melting point 117 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 or beclomethasone, sold under the brand name Vanceril among others, is a steroid medication. [5] It is available as an inhaler, cream, pills, and nasal spray. [6] The inhaled form is used in the long-term management of asthma. [5] The cream may be used for dermatitis and psoriasis. [7] The pills have been used to treat ulcerative colitis. [8] The nasal spray is used to treat allergic rhinitis and nasal polyps. [9]

Contents

Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation. [5] Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and severe allergic reactions. [5] Long-term use of the pill form may cause adrenal insufficiency. [8] The pills may also cause mood or personality changes. [8] The inhaled form is generally regarded as safe in pregnancy. [10] Beclometasone is a glucocorticoid. [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 on the World 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

Beclometasone is indicated 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

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

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. [14] [15] [16]

Nasal corticosteroids may be associated with central serous retinopathy. [17]

Pharmacology

Beclometasone is a glucocorticoid. [5] Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor [18] 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). [19]

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. [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

  1. ↑ "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025" (pdf). Therapeutic Goods Administration (TGA). May 2025. Retrieved 31 August 2025.
  2. 1 2 "Qvar Redihaler- beclomethasone dipropionate hfa aerosol, metered". DailyMed. 20 August 2025. Retrieved 1 September 2025.
  3. 1 2 "Qnasl- beclomethasone dipropionate aerosol, metered; Qnasl- beclomethasone dipropionate aerosol, metered". DailyMed. 27 September 2022. Retrieved 5 September 2025.
  4. 1 2 "Beconase- beclomethasone dipropionate monohydrate spray, suspension". DailyMed. 8 September 2010. Retrieved 5 September 2025.
  5. 1 2 3 4 5 6 7 8 9 "Beclomethasone Dipropionate". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  6. ↑ "List of products: Beclometasone dipropionate". MHRA. Archived from the original on 8 December 2015. Retrieved 6 December 2015.
  7. ↑ "Beclometasone dipropionate 0.25 mg/g Cream" (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
  8. 1 2 3 4 5 "Clipper" (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
  9. ↑ "Beclomethasone Dipropionate eent". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  10. 1 2 Hamilton 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 (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl: 10665/371090 . WHO/MHP/HPS/EML/2023.02.
  13. ↑ "Beclomethasone Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 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. Retrieved 17 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. Retrieved 17 March 2019.
  24. ↑ "Beclometasone". drugs.com. Archived from the original on 18 January 2018. Retrieved 17 March 2019.
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