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Beclometasone

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Beclometasone or beclomethasone, also known as beclomethasone dipropionate, and sold under the brand name Qvar among others, is a steroid medication.[1] It is available as an inhaler, cream, pills, and nasal spray.[2] The inhaled form is used in the long-term management of asthma.[1] The cream may be used for dermatitis and psoriasis.[3] The pills have been used to treat ulcerative colitis.[4] The nasal spray is used to treat allergic rhinitis and nasal polyps.[5]

Beclometasone
Clinical data
Trade namesQvar, Beconase AQ, others
Other namesBeclometasone dipropionate; beclomethasone dipropionate, beclomethasone (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa681047
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Inhalation, nasal, topical
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityConverted to beclometasone-17-monopropionate (17-BMP) during absorption
Protein binding87% of 17-BMP to albumin and transcortin
MetabolismBy esterase enzymes found in most tissues
Elimination half-life2.8 hours
ExcretionBiliary (60%), renal (12%)
Identifiers
  • (8S,9R,10S,11S,13S,14S,16S,17R)-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-3H-cyclopenta[a]phenanthren-17-yl propionate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.024.442 Edit this at Wikidata
Chemical and physical data
FormulaC28H37ClO7
Molar mass521.05 g·mol−1
3D model (JSmol)
Melting point117 to 120 °C (243 to 248 °F) (dec.)
  • 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/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 checkY
  • Key:KUVIULQEHSCUHY-XYWKZLDCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation.[1] Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and severe allergic reactions.[1] Long-term use of the pill form may cause adrenal insufficiency.[4] The pills may also cause mood or personality changes.[4] The inhaled form is generally regarded as safe in pregnancy.[6] Beclometasone is mainly a glucocorticoid.[1]

Beclomethasone dipropionate was first patented in 1962 and used medically in 1972.[7] It was approved for medical use in the United States in 1976.[1] It is on the World Health Organization's List of Essential Medicines.[8] In 2021, it was the 268th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[9][10]

Side effects

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Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation.[1] Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and severe allergic reactions.[1] Long-term use of the pill form may cause adrenal insufficiency.[4] The pills may also cause mood or personality changes.[4] The inhaled form is generally regarded as safe in pregnancy.[6]

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.[11][12][13] 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, hoarseness or nasal congestion, pain or headache, and visual changes. Allergic reactions may occur, but rarely.

Nasal corticosteroids may be associated with central serous retinopathy.[14]

Pharmacology

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Main article: Glucocorticoid § Pharmacology

Beclometasone is mainly a glucocorticoid.[1] Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor[15] 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).[16]

Glucocorticoids are part of the feedback mechanism in the immune system which reduces certain aspects of immune function, such as inflammation.

Names

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Beclometasone dipropionate is the INN modified and beclomethasone dipropionate is the USAN and former BAN. It is a prodrug of the free form, beclometasone (INN). The prodrug beclometasone is marketed in Norway and Russia.[17][18][19][20][21]

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

References

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  1. ^ a b c d e f g h i "Beclomethasone Dipropionate". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  2. ^ "List of products: Beclometasone dipropionate". MHRA. Archived from the original on 8 December 2015. Retrieved 6 December 2015.
  3. ^ "Beclometasone dipropionate 0.25 mg/g Cream" (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
  4. ^ a b c d e "Clipper" (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
  5. ^ "Beclomethasone Dipropionate eent". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  6. ^ a b Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 349. ISBN 9781284057560.
  7. ^ McPherson EM (2007). "Beclomethasone dipropionate". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 539. ISBN 9780815518563. Archived from the original on 8 December 2015.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  10. ^ "Beclomethasone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ 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.
  15. ^ Pelt AC (2011). Glucocorticoids: effects, action mechanisms, and therapeutic uses. Hauppauge, N.Y.: Nova Science. ISBN 978-1617287589.
  16. ^ 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.
  17. ^ 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.
  18. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 95–. ISBN 978-3-88763-075-1.
  19. ^ 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.
  20. ^ 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.
  21. ^ "Beclometasone". drugs.com. Archived from the original on 18 January 2018. Retrieved 17 March 2019.
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