用户名： 密   码：
注册 | 忘记密码？
药品详细

Beclometasone dipropionate(丙酸倍氯米松)

化学结构式图
中文名
丙酸倍氯米松
英文名
Beclometasone dipropionate
分子式
C28H37ClO7
化学名
2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
分子量
Average: 521.042
Monoisotopic: 520.222781245
CAS号
5534-09-8
ATC分类
A07E Intestinal Antiinflammatory Agents;D07A 未知;R01A 未知;R03B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Beclometasone dipropionate is a prodrug of the free form, beclometasone (beclomethasone-17-monopropionate). An anti-inflammatory, synthetic corticosteroid, it is used topically as an anti-inflammatory agent and in aerosol form for the treatment of asthma and allergic rhinitis (seasonal and perennial). 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. It is marketed under several brand names such as Qnasl (US) and Rivanase AQ (Canada).

生产厂家
  • Glaxosmithkline
  • Schering corp
  • Schering corp sub schering plough corp
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. FDA label.
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication Used in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older, and in treating symptoms for allergic rhinitis (seasonal or perennial) in patients 12 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.
Pharmacodynamics 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.
Mechanism of action Unbound corticosteroids cross cell membranes and bind with high affinity to specific cytoplasmic receptors. The result includes inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. For the investigated use in the treatment of GvHD or Crohn's, beclometasone acts by binding to interleukin-13 to inhibit cytokines, which in turn inhibits inflammatory chemicals downstream.
Absorption Mean peak plasma concentration was 88pg/ml at 0.5 hour
Volume of distribution

The steady state volume of distribution for beclomethasone dipropionate is 20 L, and for it’s active metabolite, beclomethasone-17-monopropionate, it is much larger at 424 L.
Protein binding 87% to albumin and transcortin
Metabolism
Metabolism mediated via esterase enzymes that are found in most tissues. Undergoes rapid and extensive conversion to beclomenthasone-17-monopropionate (17-BMP) during absorption
Route of 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.
Half life 2.8 hours
Clearance

High plasma clearance after intravenous administration (150 and 120 L/hour).
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
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 117-120 °C Not Available
water solubility 49.39 mg/L Not Available
logP 1.3 Not Available
Predicted Properties
Property Value Source
water solubility 2.08e-03 g/l ALOGPS
logP 3.69 ALOGPS
logP 4.43 ChemAxon
logS -5.4 ALOGPS
pKa (strongest acidic) 13.85 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 106.97 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 134.79 ChemAxon
polarizability 54.41 ChemAxon
药物相互作用
食物相互作用
  • No food effects were found when given with beclomethasone dipropionate.

返回 | 收藏