Beclometasone

Beclometasone
Names
Trade namesQvar, Beconase AQ, others
Other namesBeclomethasone (USAN); Beclometasone dipropionate; Beclomethasone dipropionate
IUPAC name
  • (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
Clinical data
Drug classCorticosteroid[1]
Main usesAsthma, allergic rhinitis, nasal polyps[2][3]
Side effectsRespiratory infections, headaches, throat inflammation[1]
Pregnancy
category
  • AU: B3
    Routes of
    use    		Inhalation, nasal, topical
    Defined daily dose0.8 mg (Inhalation aerosol) or
    0.8 mg (Inhalation powder) or
    1.5 mg (Inhalation solution)[4]
    External links
    AHFS/Drugs.comInhaled: Monograph
    Nose: Monograph
    MedlinePlusa681047
    Legal
    License data
    Legal status
    • AU: S2 (Pharmacy medicine)
    • UK: POM (Prescription only) but some nasal sprays are General sales list (GSL, OTC)
    Pharmacokinetics
    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%)
    Chemical and physical data
    FormulaC28H37ClO7
    Molar mass521.05 g·mol−1
    3D model (JSmol)
    Melting point117 to 120 °C (243 to 248 °F) (dec.)
    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
    InChI
    • 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

    Beclometasone, also known as beclometasone 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.[5] The inhaled form is used in the long-term management of asthma.[1] The cream may be used for dermatitis and psoriasis.[6] The pills have been used to treat ulcerative colitis.[7] The nasal spray is used to treat allergic rhinitis and nasal polyps.[2]

    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.[7] The pills may also cause mood or personality changes.[7] The inhaled form is generally regarded as safe in pregnancy.[8] Beclometasone is mainly a glucocorticoid.[1]

    Beclometasone dipropionate was first patented in 1962 and used medically in 1972.[9] 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 as an alternative to budesonide.[10] The wholesale price in the developing world for an inhaler containing 200 doses of medication is about US$3.20 as of 2014.[11] In the United States it costs US$50–100 for a typical month supply of the inhaled form.[12] In 2017, it was the 153rd most commonly prescribed medication in the United States, with more than four million prescriptions.[13][14]

    Medical uses

    Dosage

    The defined daily dose is 0.8 mg (Inhalation aerosol) or 0.8 mg (Inhalation powder) or 1.5 mg (Inhalation solution)[4] In adults the dose may be 100 to 500 micrograms twice per day while in children 50 to 200 micrograms twice per day may be used.[3]

    Side effects

    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.[7] The pills may also cause mood or personality changes.[7] The inhaled form is generally regarded as safe in pregnancy.[8]

    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.[15][16][17] 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.[18]

    Pharmacology

    Main article: Glucocorticoid

    Beclometasone is mainly a glucocorticoid.[1] Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor[19] 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).[20]

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

    Society and culture

    Cost

    The wholesale price in the developing world for an inhaler containing 200 doses of medication is about US$3.20 as of 2014.[11] In the United States it costs US$50–100 for a typical month supply of the inhaled form.[12] In 2017, it was the 153rd most commonly prescribed medication in the United States, with more than four million prescriptions.[13][14]

    • Beclomethasone costs (US)
      Beclomethasone costs (US)
    • Beclomethasone prescriptions (US)
      Beclomethasone prescriptions (US)

    Names

    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.[21][22][23][24][25]

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

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 "Beclomethasone Dipropionate". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved Dec 2, 2015.
    2. 1 2 "Beclomethasone Dipropionate eent". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved Dec 2, 2015.
    3. 1 2 "BECLOMETASONE aerosol - Essential drugs". medicalguidelines.msf.org. Archived from the original on 28 August 2021. Retrieved 26 August 2020.
    4. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 29 September 2020. Retrieved 22 September 2020.
    5. ↑ "List of products: BECLOMETASONE DIPROPIONATE". MHRA. Archived from the original on 8 December 2015. Retrieved 6 December 2015.
    6. ↑ "Beclometasone dipropionate 0.25 mg/g Cream" (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
    7. 1 2 3 4 5 "Clipper" (PDF). MHRA. Archived from the original (PDF) on 2015-12-08. Retrieved 6 December 2015.
    8. 1 2 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 349. ISBN 9781284057560.
    9. ↑ McPherson, Edwin M. (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 539. ISBN 9780815518563. Archived from the original on 2015-12-08.
    10. ↑ 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.
    11. 1 2 "Beclometasone". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 6 December 2015.
    12. 1 2 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 451. ISBN 9781284057560.
    13. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
    14. 1 2 "Beclomethasone - Drug Usage Statistics". ClinCalc. Archived from the original on 29 April 2017. Retrieved 11 April 2020.
    15. ↑ Willey R, Milne L, Crompton G, Grant I (1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis". Br J Dis Chest. 70 (1): 32–8. doi:10.1016/0007-0971(76)90004-8. PMID 1259918.
    16. ↑ Salzman G, Pyszczynski D (1988). "Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber". J Allergy Clin Immunol. 81 (2): 424–8. doi:10.1016/0091-6749(88)90911-6. PMID 3339197.
    17. ↑ Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S (2003). "Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone". Ann Allergy Asthma Immunol. 90 (6): 646–51. doi:10.1016/S1081-1206(10)61870-4. PMID 12839324.
    18. ↑ Haimovici R, Gragoudas ES, Duker JS, Sjaarda RN, Eliott D (October 1997). "Central serous chorioretinopathy associated with inhaled or intranasal corticosteroids". Ophthalmology. 104 (10): 1653–60. doi:10.1016/s0161-6420(97)30082-7. PMID 9331207.
    19. ↑ Pelt AC (2011). Glucocorticoids: effects, action mechanisms, and therapeutic uses. Hauppauge, N.Y.: Nova Science. ISBN 978-1617287589.
    20. ↑ Rhen T, Cidlowski JA (Oct 2005). "Antiinflammatory action of glucocorticoids--new mechanisms for old drugs". The New England Journal of Medicine. 353 (16): 1711–23. doi:10.1056/NEJMra050541. PMID 16236742.
    21. ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 123–. ISBN 978-1-4757-2085-3.
    22. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 95–. ISBN 978-3-88763-075-1. Archived from the original on 2019-12-15. Retrieved 2019-03-17.
    23. ↑ I.K. Morton; Judith M. Hall (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 15 December 2019. Retrieved 17 March 2019.
    24. ↑ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 141–. ISBN 978-3-7692-2114-5. Archived from the original on 15 December 2019. Retrieved 17 March 2019.
    25. ↑ "Beclometasone". drugs.com. Archived from the original on 2018-01-18. Retrieved 2019-03-17.
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