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Beclometasone

January 01, 1970

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
  • 5534-09-8 Y
PubChem CID
  • 21700
IUPHAR/BPS
  • 5894
DrugBank
  • DB00394 N
ChemSpider
  • 20396 Y
UNII
  • 5B307S63B2
KEGG
  • D00689
ChEBI
  • CHEBI:3002 Y
ChEMBL
  • ChEMBL1200500 N
CompTox Dashboard (EPA)
  • DTXSID3048730
ECHA InfoCard100.024.442
Chemical and physical data
FormulaC28H37ClO7
Molar mass521.05 g·mol−1
3D model (JSmol)
  • Interactive image
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 Y
  • Key:KUVIULQEHSCUHY-XYWKZLDCSA-N Y
 NY (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 edit

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 edit

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 edit

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 edit

  1. ^ a b c d e f g h i "Beclomethasone Dipropionate". The American Society of Health-System Pharmacists. from the original on 8 December 2015. Retrieved 2 December 2015.
  2. ^ "List of products: Beclometasone dipropionate". MHRA. from the original on 8 December 2015. Retrieved 6 December 2015.
  3. ^ (PDF). MHRA. Archived from the original (PDF) on 8 December 2015. Retrieved 6 December 2015.
  4. ^ a b c d e (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. 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. 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. 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. 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. from the original on 12 January 2023. Retrieved 17 March 2019.
  21. ^ "Beclometasone". drugs.com. from the original on 18 January 2018. Retrieved 17 March 2019.

January 01, 1970
beclometasone, beclomethasone, also, known, beclomethasone, dipropionate, sold, under, brand, name, qvar, among, others, steroid, medication, available, inhaler, cream, pills, nasal, spray, inhaled, form, used, long, term, management, asthma, cream, used, derm. 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 BeclometasoneClinical dataTrade namesQvar Beconase AQ othersOther namesBeclometasone dipropionate beclomethasone dipropionate beclomethasone USAN US AHFS Drugs comMonographMedlinePlusa681047License dataUS DailyMed BeclomethasonePregnancycategoryAU B3Routes ofadministrationInhalation nasal topicalATC codeA07EA07 WHO D07AC15 WHO R01AD01 WHO R03BA01 WHO Legal statusLegal statusAU S2 Pharmacy medicine UK POM Prescription only but some nasal sprays are General sales list GSL OTC US onlyPharmacokinetic dataBioavailabilityConverted to beclometasone 17 monopropionate 17 BMP during absorptionProtein binding87 of 17 BMP to albumin and transcortinMetabolismBy esterase enzymes found in most tissuesElimination half life2 8 hoursExcretionBiliary 60 renal 12 IdentifiersIUPAC 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 propionateCAS Number5534 09 8 YPubChem CID21700IUPHAR BPS5894DrugBankDB00394 NChemSpider20396 YUNII5B307S63B2KEGGD00689ChEBICHEBI 3002 YChEMBLChEMBL1200500 NCompTox Dashboard EPA DTXSID3048730ECHA InfoCard100 024 442Chemical and physical dataFormulaC 28H 37Cl O 7Molar mass521 05 g mol 13D model JSmol Interactive imageMelting 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 CCInChI 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 YKey KUVIULQEHSCUHY XYWKZLDCSA N Y N Y 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 Contents 1 Side effects 2 Pharmacology 3 Names 4 ReferencesSide effects editCommon 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 editMain 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 editBeclometasone 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 edit 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 List of products Beclometasone dipropionate MHRA Archived from the original on 8 December 2015 Retrieved 6 December 2015 Beclometasone dipropionate 0 25 mg g Cream PDF MHRA Archived from the original PDF on 8 December 2015 Retrieved 6 December 2015 a b c d e Clipper PDF MHRA Archived from the original PDF on 8 December 2015 Retrieved 6 December 2015 Beclomethasone Dipropionate eent The American Society of Health System Pharmacists Archived from the original on 8 December 2015 Retrieved 2 December 2015 a b Hamilton R 2015 Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab Coat Edition Jones amp Bartlett Learning p 349 ISBN 9781284057560 McPherson EM 2007 Beclomethasone dipropionate Pharmaceutical Manufacturing Encyclopedia 3rd ed Burlington Elsevier p 539 ISBN 9780815518563 Archived from the original on 8 December 2015 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 The Top 300 of 2021 ClinCalc Archived from the original on 15 January 2024 Retrieved 14 January 2024 Beclomethasone Drug Usage Statistics ClinCalc Retrieved 14 January 2024 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 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 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 amp Immunology 90 6 646 651 doi 10 1016 S1081 1206 10 61870 4 PMID 12839324 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 Pelt AC 2011 Glucocorticoids effects action mechanisms and therapeutic uses Hauppauge N Y Nova Science ISBN 978 1617287589 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 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 Index Nominum 2000 International Drug Directory Taylor amp Francis 2000 pp 95 ISBN 978 3 88763 075 1 Morton IK Hall JM 6 December 2012 Concise Dictionary of Pharmacological Agents Properties and Synonyms Springer Science amp Business Media pp 46 ISBN 978 94 011 4439 1 Archived from the original on 12 January 2023 Retrieved 17 March 2019 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 Beclometasone drugs com Archived from the original on 18 January 2018 Retrieved 17 March 2019 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Beclometasone amp oldid 1215843470, wikipedia, wiki, book, books, library,

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