Beclometasone
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Hodoodo CAT#: H584226

CAS#: 4419-39-0

Description: Beclometasone, also known as Beclomethasone, is an anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of asthma.


Chemical Structure

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Beclometasone
CAS# 4419-39-0

Theoretical Analysis

Hodoodo Cat#: H584226
Name: Beclometasone
CAS#: 4419-39-0
Chemical Formula: C22H29ClO5
Exact Mass: 408.17
Molecular Weight: 408.919
Elemental Analysis: C, 64.62; H, 7.15; Cl, 8.67; O, 19.56

Price and Availability

Size Price Availability Quantity
100mg USD 340 2 weeks
250mg USD 670 2 weeks
1g USD 1580 2 weeks
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Synonym: Beclometasone; Beclomethasone

IUPAC/Chemical Name: 9-Chloro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione

InChi Key: NBMKJKDGKREAPL-DVTGEIKXSA-N

InChi Code: 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

SMILES Code: C[C@@]12[C@](C(CO)=O)(O)[C@@H](C)C[C@@]1([H])[C@]3([H])CCC4=CC(C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Beclometasone is a glucocorticoid receptor agonist.
In vitro activity: The effects of dexamethasone (Dex) and beclomethasone (Beclo) on C. pneumoniae infection in vitro were evaluated. Glucocorticoids were tested alone or in combination with azithromycin (AZM), telithromycin (TEL), or levofloxacin (LVX), antibiotics commonly used against C. pneumoniae infections. In vitro at 1 and 5 μM, both glucocorticoids decreased the number of IFU (inclusion forming units) versus the control number (P < 0.001). Dex and Beclo reduced the number of IFU versus the control number by about 25% at 1 μM and by about 40 and 30%, respectively, at 5 μM. Reference: Antimicrob Agents Chemother. 2004 Dec;48(12):4878-81. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC529217/
In vivo activity: The in vivo antichlamydial activities of dexamethasone and beclomethasone alone and in combination with an antibiotic were tested. An in vivo dose of Dex and Beclo (120 μg/kg/day) led to an anti-inflammatory effect and an immunosuppressant effect in a murine Chlamydophila pneumoniae infection model. Reference: Antimicrob Agents Chemother. 2004 Dec;48(12):4878-81. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC529217/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 73.36
DMF 30.0 73.36

Preparing Stock Solutions

The following data is based on the product molecular weight 408.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Caronzolo D, Lucini V, Pannacci M, Grosso S, Colleoni F, Fraschini F, Scaglione F. Glucocorticoids increase in vitro and in vivo activities of antibiotics against Chlamydophila pneumoniae. Antimicrob Agents Chemother. 2004 Dec;48(12):4878-81. doi: 10.1128/AAC.48.12.4878-4881.2004. PMID: 15561871; PMCID: PMC529217.
In vitro protocol: 1. Caronzolo D, Lucini V, Pannacci M, Grosso S, Colleoni F, Fraschini F, Scaglione F. Glucocorticoids increase in vitro and in vivo activities of antibiotics against Chlamydophila pneumoniae. Antimicrob Agents Chemother. 2004 Dec;48(12):4878-81. doi: 10.1128/AAC.48.12.4878-4881.2004. PMID: 15561871; PMCID: PMC529217.
In vivo protocol: 1. Caronzolo D, Lucini V, Pannacci M, Grosso S, Colleoni F, Fraschini F, Scaglione F. Glucocorticoids increase in vitro and in vivo activities of antibiotics against Chlamydophila pneumoniae. Antimicrob Agents Chemother. 2004 Dec;48(12):4878-81. doi: 10.1128/AAC.48.12.4878-4881.2004. PMID: 15561871; PMCID: PMC529217.

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1: Sharif M, Khan BT, Sharif M. Protective effects of beclomethasone against insulin induced airway hyper-reactivity in guinea pig and exploration of its mechanism of action. J Ayub Med Coll Abbottabad. 2014 Jan-Mar;26(1):3-6. PubMed PMID: 25358205.

2: Chassot JM, Ribas D, Silveira EF, Grünspan LD, Pires CC, Farago PV, Braganhol E, Tasso L, Cruz L. Beclomethasone Dipropionate-Loaded Polymeric Nanocapsules: Development, In Vitro Cytotoxicity, and In Vivo Evaluation of Acute Lung Injury. J Nanosci Nanotechnol. 2015 Jan;15(1):855-64. PubMed PMID: 26328450.

3: Storms WW, Segall N, Mansfield LE, Amar NJ, Kelley L, Ding Y, Tantry SK. Efficacy and safety of beclomethasone dipropionate nasal aerosol in pediatric patients with seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2013 Nov;111(5):408-414.e1. doi: 10.1016/j.anai.2013.07.033. Epub 2013 Aug 28. PubMed PMID: 24125150.

4: Boyd SD, Hadigan C, McManus M, Chairez C, Nieman LK, Pau AK, Alfaro RM, Kovacs JA, Calderon MM, Penzak SR. Influence of low-dose ritonavir with and without darunavir on the pharmacokinetics and pharmacodynamics of inhaled beclomethasone. J Acquir Immune Defic Syndr. 2013 Jul 1;63(3):355-61. doi: 10.1097/QAI.0b013e31829260d6. PubMed PMID: 23535292; PubMed Central PMCID: PMC3683093.

5: Leach CL, Kuehl PJ, Chand R, Ketai L, Norenberg JP, McDonald JD. Characterization of respiratory deposition of fluticasone-salmeterol hydrofluoroalkane-134a and hydrofluoroalkane-134a beclomethasone in asthmatic patients. Ann Allergy Asthma Immunol. 2012 Mar;108(3):195-200. doi: 10.1016/j.anai.2012.01.010. PubMed PMID: 22374204.

6: Jaafar-Maalej C, Andrieu V, Elaissari A, Fessi H. Beclomethasone-loaded lipidic nanocarriers for pulmonary drug delivery: preparation, characterization and in vitro drug release. J Nanosci Nanotechnol. 2011 Mar;11(3):1841-51. PubMed PMID: 21449319.

7: Meltzer EO, Jacobs RL, LaForce CF, Kelley CL, Dunbar SA, Tantry SK. Safety and efficacy of once-daily treatment with beclomethasone dipropionate nasal aerosol in subjects with perennial allergic rhinitis. Allergy Asthma Proc. 2012 May-Jun;33(3):249-57. PubMed PMID: 22737708.

8: Morrow Brown H, Bergmann KC, Ring J. Harry Morrow Brown (1917-2013). Derby, UK. Chem Immunol Allergy. 2014;100:365-7. doi: 10.1159/000360106. Epub 2014 May 22. PubMed PMID: 24925424.

9: Chawes BL, Piccinno A, Kreiner-Møller E, Vissing NH, Poorisrisak P, Mortensen L, Nilson E, Bisgaard A, Dossing A, Deleuran M, Skytt NL, Samandari N, Sergio F, Ciurlia G, Poli G, Acerbi D, Bisgaard H. Pharmacokinetic comparison of inhaled fixed combination vs. the free combination of beclomethasone and formoterol pMDIs in asthmatic children. Br J Clin Pharmacol. 2013 Apr;75(4):1081-8. doi: 10.1111/j.1365-2125.2012.04459.x. PubMed PMID: 22978252; PubMed Central PMCID: PMC3612726.

10: van Bavel JH, Ratner PH, Amar NJ, Hampel FC Jr, Melchior A, Dunbar SA, Dorinsky PM, Tantry SK. Efficacy and safety of once-daily treatment with beclomethasone dipropionate nasal aerosol in subjects with seasonal allergic rhinitis. Allergy Asthma Proc. 2012 Sep-Oct;33(5):386-96. doi: 10.2500/aap.2012.33.3593. PubMed PMID: 23026180.

11: Chien JW, Sakai M, Gooley TA, Schoch HG, McDonald GB. Influence of oral beclomethasone dipropionate on early non-infectious pulmonary outcomes after allogeneic hematopoietic cell transplantation: results from two randomized trials. Bone Marrow Transplant. 2010 Feb;45(2):317-24. doi: 10.1038/bmt.2009.129. Epub 2009 Jun 29. PubMed PMID: 19561649; PubMed Central PMCID: PMC2820152.

12: Fascì Spurio F, Aratari A, Margagnoni G, Doddato MT, Chiesara F, Papi C. Oral beclomethasone dipropionate: a critical review of its use in the management of ulcerative colitis and Crohn's disease. Curr Clin Pharmacol. 2012 May;7(2):131-6. Review. PubMed PMID: 22432845.

13: Kuna P, Govoni M, Lucci G, Scuri M, Acerbi D, Stelmach I. Pharmacokinetics and pharmacodynamics of an extrafine fixed pMDI combination of beclometasone dipropionate/formoterol fumarate in adolescent asthma. Br J Clin Pharmacol. 2015 Sep;80(3):569-80. doi: 10.1111/bcp.12640. Epub 2015 Jun 1. PubMed PMID: 25808292; PubMed Central PMCID: PMC4574841.

14: Gerzeli S, Rognoni C, Quaglini S, Cavallo MC, Cremonesi G, Papi A. Cost-effectiveness and cost-utility of beclomethasone/formoterol versus fluticasone propionate/salmeterol in patients with moderate to severe asthma. Clin Drug Investig. 2012 Apr 1;32(4):253-65. doi: 10.2165/11598940-000000000-00000. PubMed PMID: 22352412.

15: Camargos PA, Lasmar LM. Effects of beclomethasone and factors related to asthma on the growth of prepubertal children. Respir Med. 2010 Jul;104(7):951-6. doi: 10.1016/j.rmed.2010.02.002. Epub 2010 Feb 26. PubMed PMID: 20189373.

16: Holmberg K, Pipkorn U. Influence of topical beclomethasone dipropionate suspension on human nasal mucociliary activity. Eur J Clin Pharmacol. 1986;30(5):625-7. PubMed PMID: 3758151.

17: Mansfield LE. Beclomethasone HFA for the treatment of allergic rhinitis. Expert Opin Pharmacother. 2015;16(18):2849-57. doi: 10.1517/14656566.2015.1115014. Epub 2015 Dec 11. Review. PubMed PMID: 26653155.

18: Blair H, Butler AG. Intranasal beclomethasone dipropionate in seasonal rhinitis in general practice. Practitioner. 1976 Mar;216(1293):347-51. PubMed PMID: 4785.

19: Price D, Thomas M, Haughney J, Lewis RA, Burden A, von Ziegenweidt J, Chisholm A, Hillyer EV, Corrigan CJ. Real-life comparison of beclometasone dipropionate as an extrafine- or larger-particle formulation for asthma. Respir Med. 2013 Jul;107(7):987-1000. doi: 10.1016/j.rmed.2013.03.009. Epub 2013 May 3. PubMed PMID: 23643486.

20: Boner AL, Piacentini GL, Bonizzato C, Dattoli V, Sette L. Effect of inhaled beclomethasone dipropionate on bronchial hyperreactivity in asthmatic children during maximal allergen exposure. Pediatr Pulmonol. 1991;10(1):2-5. PubMed PMID: 2003042.