5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid

• ChemBase编号: 1119
• 分子式: C14H10N2O6
• 平均质量: 302.239
• 单一同位素质量: 302.05388605
• SMILES: c1(cc(c(cc1)O)C(=O)O)/N=N/c1cc(c(cc1)O)C(=O)O
• Canonical SMILES: OC(=O)c1cc(/N=N/c2ccc(c(c2)C(=O)O)O)ccc1O
• InChI: InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+
• InChIKey: QQBDLJCYGRGAKP-FOCLMDBBSA-N

名称和登记号

名称

• IUPAC标准名: 5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
• IUPAC传统名: olsalazine
• 商标名: Dipentum
• 别名: Olsalazine sodium; Olsalazine

登记号

• CAS号: 15722-48-2
• PubChem SID: 160964582; 46506356
• PubChem CID: 6003770

理论计算性质

JChem

• Acid pKa: 2.926956
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -0.11579686
• LogD (pH = 7.4): -2.4937713
• Log P: 4.3871746
• 摩尔折射率: 78.8512 cm^3
• 极化性: 27.597473 Å^3
• 极化表面积: 139.78 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -3.59
• 溶解度: 7.81e-02 g/l

分子性质

理化性质

• 溶解度: 0.0817 mg/mL [Predicted by ALOGPS]
• 疏水性(logP): 2.3

详细说明

DrugBank - DB01250

• Drug Groups: approved
• Description: 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.
• Indication: For the treatment of Inflammatory Bowel Disease and Ulcerative Colitis.
• Pharmacology: 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.
• 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
• Biotransformation: 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)
• 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.
• Half Life: Olsalazine has an elimination half-life of 0.9 hours, however, olsalazine-S has a half-life of 7 days.
• Protein Binding: Olsalazine and olsalazine-S are more than 99% bound to plasma proteins. Mesalamine (5-ASA) is 74% bound to plasma proteins.
• 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.
• External Links: Wikipedia; RxList; Drugs.com