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5534-09-8 分子结构
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(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编号:277
分子式:C22H29ClO5
平均质量:408.91566
单一同位素质量:408.17035171
SMILES和InChIs

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

引用这个纪录

CBID:277 http://www.chembase.cn/molecule-277.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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
(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传统名
beclomethasone
商标名
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
别名
(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
CAS号
5534-09-8
4419-39-0
PubChem SID
160963740
PubChem CID
20469

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
TRC
B131000 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.43441  质子受体
质子供体 LogD (pH = 5.5) 2.1450696 
LogD (pH = 7.4) 2.1450658  Log P 2.1450698 
摩尔折射率 107.236 cm3 极化性 41.7352 Å3
极化表面积 94.83 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.12  LOG S -3.78 
溶解度 6.84e-02 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
49.39 mg/L expand 查看数据来源
Dioxane expand 查看数据来源
DMSO expand 查看数据来源
Ethyl Acetate expand 查看数据来源
Methanol expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
180-182°C (dec.) expand 查看数据来源
疏水性(logP)
1.3 expand 查看数据来源
保存条件
-20°C Freezer, Under inert atmosphere expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB00394 external link
Item Information
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 external link
Glucocorticoid. Used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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)
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专利

专利

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