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药品详细

Balsalazide(巴柳氮)

化学结构式图
中文名
巴柳氮
英文名
Balsalazide
分子式
C17H15N3O6
化学名
5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid
分子量
Average: 357.3175
Monoisotopic: 357.096085227
CAS号
80573-04-2
ATC分类
A07E Intestinal Antiinflammatory Agents
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Balsalazide is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease. It is sold under the name “Colazal” in the US and “Colazide” in the UK.

The chemical name is (E)-5-[[-4-(2-carboxyethyl) aminocarbonyl] phenyl]azo] -2-hydroxybenzoic acid. It is usually administered as the disodium salt.

Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA, in the large intestine. Its advantage over that drug in the treatment of Ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis.

生产厂家
  • Apotex inc etobicoke site
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Salix pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. Pubmed
  2. Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication For the treatment of mildly to moderately active ulcerative colitis.
Pharmacodynamics Balsalazide is a prodrug that has little or no pharmacologic activity until it is enzymatically cleaved in the colon to produce mesalamine (5-aminosalicylic acid), an anti inflammatory drug indicated for the treatment of mildly to moderately active ulcerative colitis. Balsalazide disodium is delivered intact to the colon where it is cleaved by bacterial azoreduction to release equimolar quantities of mesalamine, which is the therapeutically active portion of the molecule, and the intert 4-aminobenzoyl-(beta)-alanine. As a result, the spectrum of pharmacologic activity of balsalazide is similar to that of mesalamine.
Mechanism of action The mechanism of action of 5-aminosalicylic acid is unknown, but appears exert its anti-inflammatory effects locally (in the GI tract) rather than systemically. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways (catalyzes the formation of prostaglandin precursors from arachidonic acid), and through the lipoxygenase pathways (catalyzes the formation of leukotrienes and hydroxyeicosatetraenoic acids from arachidonic acid and its metabolites), is increased in patients with chronic inflammatory bowel disease. Therefore, it is possible that 5-aminosalicylic acid diminishes inflammation by blocking production of arachidonic acid metabolites in the colon through both the inhibition of cyclooxygenase and lipoxygenase.
Absorption Low and variable, intact balsalazide is poorly absorbed systemically.
Volume of distribution Not Available
Protein binding ≥99%
Metabolism
Cleaved in the colon via bacterial azoreduction to 5–aminosalicylic acid (5–ASA) and 4–aminobenzoyl-beta-alanine, the inactive carrier moiety.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Balsalazide
5-aminosalicylic acid Details
Balsalazide
    		4-aminobenzoyl-(beta)-alanine Details
    Route of elimination The products of the azoreduction of this compound, 5-ASA and 4-aminobenzoyl-ß-alanine, and their N-acetylated metabolites have been identified in plasma, urine and feces. Following single-dose administration of 2.25 g COLAZAL (three 750 mg capsules) under fasting conditions in healthy subjects, mean urinary recovery of balsalazide, 5-ASA, and N-Ac-5-ASA was 0.20%, 0.22% and 10.2%, respectively.
    Half life Half-life could not be determined.
    Clearance Not Available
    Toxicity A single oral dose of balsalazide disodium at 5 grams/kg or 4-aminobenzoyl-(beta)-alanine, a metabolite of balsalazide disodium, at 1 gram/kg was non-lethal in mice and rats. No symptoms of acute toxicity were seen at these doses.
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    water solubility Freely soluble as disodium salt Not Available
    logP 1.3 Not Available
    Predicted Properties
    Property Value Source
    water solubility 6.21e-02 g/l ALOGPS
    logP 3.37 ALOGPS
    logP 3.17 ChemAxon
    logS -3.8 ALOGPS
    pKa (strongest acidic) 3.06 ChemAxon
    pKa (strongest basic) -0.033 ChemAxon
    physiological charge -2 ChemAxon
    hydrogen acceptor count 8 ChemAxon
    hydrogen donor count 4 ChemAxon
    polar surface area 148.65 ChemAxon
    rotatable bond count 7 ChemAxon
    refractivity 94.37 ChemAxon
    polarizability 35.98 ChemAxon
    药物相互作用
    食物相互作用
    Not Available

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