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药品详细

Olsalazine(奥沙拉嗪)

化学结构式图
中文名
奥沙拉嗪
英文名
Olsalazine
分子式
C14H10N2O6
化学名
5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
分子量
Average: 302.239
Monoisotopic: 302.053886062
CAS号
15722-48-2
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

Olsalazine is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease and Ulcerative Colitis. Olsalazine is a derivative of salicylic acid. Inactive by itself (it is a prodrug), it is converted by the bacteria in the colon to mesalamine. Mesalamine works as an anti-inflammatory agent in treating inflammatory diseases of the intestines.

生产厂家
  • Ucb inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Salicylates and Derivatives
  • Aminobenzoates
  • Aminophenols and Derivatives
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Keto-Acids
  • Benzoates
  • Hydrazones
  • Salicylates and Derivatives
  • Phenols and Derivatives
  • Carboxylic Acids and Derivatives
  • Benzene and Derivatives
  • Aminobenzoates
  • Aminophenols and Derivatives
  • Aromatic compounds
  • Hydrazine Derivatives
  • Imines
  • Benzoyl Derivatives
  • Phenylhydrazines
  • Phenyl Esters
  • Anilines
  • Ketones
适应症
药理
Indication For the treatment of Inflammatory Bowel Disease and Ulcerative Colitis.
Pharmacodynamics Olsalazine is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease and Ulcerative Colitis. Olsalazine reduces the bowel inflammation, diarrhea (stool frequency), rectal bleeding, and abdominal pain. Like Balsalazide, Olsalazine is believed to deliver Mesalazine, or 5-aminosalicylic acid (5-ASA), past the small intestine, directly to the large intestine, which is that active site of disease in ulcerative colitis.
Mechanism of action Orally administered olsalazine is converted to mesalamine which is thought to be the therapeutically active agent in the treatment of ulcerative colitis. The mechanism of action of mesalamine (and sulfasalazine) is unknown, but appears to be topical rather than systemic. Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes (LTs) and hydroxyelcosatetraenoic acids (HETEs) is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalamine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin (PG) production in the colon.
Absorption After oral administration, olsalazine, has limited systemic bioavailability. 98-99% of the dose is converted to mesalamine (5-ASA) in the colon, which is absorbed slowly resulting in very high local concentrations in the colon.
Volume of distribution Not Available
Protein binding Olsalazine and olsalazine-S are more than 99% bound to plasma proteins. Mesalamine (5-ASA) is 74% bound to plasma proteins.
Metabolism
Most (98 to 99%) of an oral dose is rapidly converted into two molecules of 5-aminosalicylic acid (5-ASA) by colonic bacteria and the low prevailing redox potential found in this environment. The conversion of olsalazine to mesalamine in the colon is similar to that of sulfasalazine, which is converted into sulfapyridine and mesalamine. Approximately 0.1% of an oral dose of olsalazine is metabolized in the liver to olsalazine-O-sulfate (olsalazine-S)

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

Substrate Enzymes Product
Olsalazine
    		Olsalazine-O-sulfate Details
    Route of elimination Approximately 0.1% of an oral dose of olsalazine is metabolized in the liver to olsalazine-O-sulfate (olsalazine-S).The remaining 5-ASA is partially acetylated and is excreted in the feces.
    Half life Olsalazine has an elimination half-life of 0.9 hours, however, olsalazine-S has a half-life of 7 days.
    Clearance Not Available
    Toxicity Maximum single oral doses of 5g/kg in mice and rats and 2 g/kg in dogs were not lethal.
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point Sodium salt decomposes at 240 °C Not Available
    logP 2.3 Not Available
    Caco2 permeability -6.96 ADME Research, USCD
    Predicted Properties
    Property Value Source
    water solubility 7.81e-02 g/l ALOGPS
    logP 2.77 ALOGPS
    logP 4.39 ChemAxon
    logS -3.6 ALOGPS
    pKa (strongest acidic) 2.93 ChemAxon
    pKa (strongest basic) -0.019 ChemAxon
    physiological charge -2 ChemAxon
    hydrogen acceptor count 8 ChemAxon
    hydrogen donor count 4 ChemAxon
    polar surface area 139.78 ChemAxon
    rotatable bond count 4 ChemAxon
    refractivity 78.85 ChemAxon
    polarizability 28.61 ChemAxon
    药物相互作用
    Drug Interaction
    Azathioprine Olsalazine may increase the toxicity of thiopurine, azathioprine.
    Mercaptopurine Olsalazine may increase the toxicity of thiopurine, mercaptopurine.
    Thioguanine Olsalazine may increase the toxicity of thiopurine, thioguanine.
    食物相互作用
    Not Available

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