(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 277
• Molecular Formular: C22H29ClO5
• Molecular Mass: 408.91566
• Monoisotopic Mass: 408.17035171
• SMILES: Cl[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl
• InChI: 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
• InChIKey: NBMKJKDGKREAPL-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: beclomethasone
• Brand Name: QVAR 80; Rino-Clenil; Sanasthmax; Sanasthmyl; Vancenase; Vancenase AQ; Vanceril; Vanceril Double Strength; Viarex; Viarox; Aerobec; Aldecin; Anceron; Andion; Beclacin; Becloforte; Beclomet; Beclometasondipropionat Mikron; Beclorhinol; Becloval; Beclovent; Becodisks; Beconase; Beconase AQ; Beconasol; Becotide; Clenil-A; Entyderma; Inalone; Korbutone; Propaderm; QVAR
• Synonyms: (11β,16β)-9-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 9α-Chloro-16β-methylprednisolone; Becolvent; Beclometasona [INN-Spanish]; Beclometasonum [INN-Latin]; Beclometasone; Beclomethasone

Database IDs

• CAS Number: 5534-09-8; 4419-39-0
• PubChem SID: 160963740
• PubChem CID: 20469

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.43441
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.1450696
• LogD (pH = 7.4): 2.1450658
• Log P: 2.1450698
• Molar Refractivity: 107.236 cm^3
• Polarizability: 41.7352 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.12
• LOG S: -3.78
• Solubility (Water): 6.84e-02 g/l

PROPERTIES

Physical Property

• Solubility: 49.39 mg/L; Dioxane; DMSO; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 180-182°C (dec.)
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere

DETAILS

DrugBank - DB00394

• Drug Groups: approved
• Description: Beclometasone dipropionate is a prodrug of the free form, beclometasone. An anti-inflammatory, synthetic glucocorticoid, it is used topically as an anti-inflammatory agent and in aerosol form for the treatment of asthma. Beclometasone dipropionate is also being investigated for oral treatment in mild-to-moderate Crohn's disease of ileal or ileal-right colonic localisation and for "topical" use mild-to-moderate graft versus host disease.
• Indication: For the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. Also being investigated for oral treatment in mild-to-moderate Crohn's disease of ileal or ileal-right colonic localisation and for "topical" use mild-to-moderate graft versus host disease.
• Pharmacology: Beclometasone, a synthetic halogenated glucocorticoid with antiinflammatory and vasoconstrictive effects, is used for treating steroid-dependent asthma, allergic or nonallergic rhinitis, or recurrent nasal polyps.
• Toxicity: The acute toxicity of beclometasone dipropionate is low. The only harmful effect that follows inhalation of large amounts of the drug over a short period of time is suppression of hypothalamic-pituitary-adrenal (HPA) function. Chronic: The excessive use of beclometasone dipropionate over a long period could lead to adrenal suppression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism mediated via esterase enzymes that are found in most tissues. Undergoes rapid and extensive conversion to beclomenthasone-17-monopropionate (17-BMP) during absorption
• Absorption: Mean peak plasma concentration was 88pg/ml at 0.5 hour
• Half Life: 2.8 hours
• Protein Binding: 87% to albumin and transcortin
• Elimination: Irrespective of the route of administration (injection, oral or inhalation), BDP and its metabolites are mainly excreted in the feces. Less than 10% of the drug and its metabolites are excreted in the urine.
• Clearance: High plasma clearance after intravenous administration (150 and 120 L/hour).
• References: Willey RF, Milne LJ, Crompton GK, Grant IW: Beclomethasone dipropionate aerosol and oropharyngeal candidiasis. Br J Dis Chest. 1976 Jan;70(1):32-8. [Pubmed] ; Salzman GA, Pyszczynski DR: Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber. J Allergy Clin Immunol. 1988 Feb;81(2):424-8. [Pubmed] ; Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S: Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone. Ann Allergy Asthma Immunol. 2003 Jun;90(6):646-51. [Pubmed] ; Astegiano M, Pagano N, Sapone N, Simondi D, Bertolusso L, Bresso F, Demarchi B, Pellicano R, Bonardi R, Marconi S, Rizzetto M: Efficacy and safety of oral beclomethasone dipropionate for ileal or ileal-right colon Crohn's disease of mild-to-moderate activity or in remission: Retrospective study. Biomed Pharmacother. 2007 Jul;61(6):370-6. Epub 2007 Mar 12. [Pubmed] ; McDonald GB: Oral beclomethasone dipropionate: a topically active corticosteroid for the treatment of gastrointestinal graft-versus-host disease following allogeneic hematopoietic cell transplantation. Expert Opin Investig Drugs. 2007 Oct;16(10):1709-24. [Pubmed] ; Hockenbery DM, Cruickshank S, Rodell TC, Gooley T, Schuening F, Rowley S, David D, Brunvand M, Berryman B, Abhyankar S, Bouvier M, McDonald GB: A randomized, placebo-controlled trial of oral beclomethasone dipropionate as a prednisone-sparing therapy for gastrointestinal graft-versus-host disease. Blood. 2007 May 15;109(10):4557-63. Epub 2007 Jan 23. [Pubmed] ; Castilla C, Perez-Simon JA, Sanchez-Guijo FM, Diez-Campelo M, Ocio E, Perez-Persona E, Lopez-Villar O, Vazquez L, Caballero D, San Miguel JF: Oral beclomethasone dipropionate for the treatment of gastrointestinal acute graft-versus-host disease (GVHD). Biol Blood Marrow Transplant. 2006 Sep;12(9):936-41. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - B131000

Glucocorticoid. Used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).

REFERENCES

• Willey RF, Milne LJ, Crompton GK, Grant IW: Beclomethasone dipropionate aerosol and oropharyngeal candidiasis. Br J Dis Chest. 1976 Jan;70(1):32-8. Pubmed
• Salzman GA, Pyszczynski DR: Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber. J Allergy Clin Immunol. 1988 Feb;81(2):424-8. Pubmed
• Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S: Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone. Ann Allergy Asthma Immunol. 2003 Jun;90(6):646-51. Pubmed
• Astegiano M, Pagano N, Sapone N, Simondi D, Bertolusso L, Bresso F, Demarchi B, Pellicano R, Bonardi R, Marconi S, Rizzetto M: Efficacy and safety of oral beclomethasone dipropionate for ileal or ileal-right colon Crohn's disease of mild-to-moderate activity or in remission: Retrospective study. Biomed Pharmacother. 2007 Jul;61(6):370-6. Epub 2007 Mar 12. Pubmed
• McDonald GB: Oral beclomethasone dipropionate: a topically active corticosteroid for the treatment of gastrointestinal graft-versus-host disease following allogeneic hematopoietic cell transplantation. Expert Opin Investig Drugs. 2007 Oct;16(10):1709-24. Pubmed
• Hockenbery DM, Cruickshank S, Rodell TC, Gooley T, Schuening F, Rowley S, David D, Brunvand M, Berryman B, Abhyankar S, Bouvier M, McDonald GB: A randomized, placebo-controlled trial of oral beclomethasone dipropionate as a prednisone-sparing therapy for gastrointestinal graft-versus-host disease. Blood. 2007 May 15;109(10):4557-63. Epub 2007 Jan 23. Pubmed
• Castilla C, Perez-Simon JA, Sanchez-Guijo FM, Diez-Campelo M, Ocio E, Perez-Persona E, Lopez-Villar O, Vazquez L, Caballero D, San Miguel JF: Oral beclomethasone dipropionate for the treatment of gastrointestinal acute graft-versus-host disease (GVHD). Biol Blood Marrow Transplant. 2006 Sep;12(9):936-41. Pubmed
• Malfitan, V.A., et al.: Clin. Ther., 4, 472 (1982)
• Rao, M., et al.: J. Asthma, 19, 21 (1982)
• Small, P., et al.: Ann. Allergy, 49, 127 (1982)
• Brogden, R.N., et al.: Drugs, 28, 99 (1982)