(3Z)-3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazin-1-ylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid

• ChemBase编号: 887
• 分子式: C17H15N3O6
• 平均质量: 357.3175
• 单一同位素质量: 357.09608522
• SMILES: O=C(NCCC(=O)O)c1ccc(N/N=C/2\C=C(C(=O)C=C2)C(=O)O)cc1
• Canonical SMILES: OC(=O)CCNC(=O)c1ccc(cc1)N/N=C\1/C=CC(=O)C(=C1)C(=O)O
• InChI: InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,19H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-12-
• InChIKey: KONZVQJABTUMFX-NDENLUEZSA-N

名称和登记号

名称

• IUPAC标准名: (3Z)-3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazin-1-ylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid
• IUPAC传统名: colazal
• 商标名: Carbadox; Colazal
• 别名: Balsalazido [Spanish]; Balsalazida [Spanish]; Balsalazide disodium; Balsalazidum [Latin]; balsalazide; Balsalazide

登记号

• CAS号: 80573-04-2
• PubChem SID: 160964350
• PubChem CID: 6335412

理论计算性质

JChem

• Acid pKa: 3.2294433
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.9421471
• LogD (pH = 7.4): -4.9961586
• Log P: -0.07333821
• 摩尔折射率: 93.5999 cm^3
• 极化性: 33.484524 Å^3
• 极化表面积: 145.16 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.91
• LOG S: -4.11
• 溶解度: 2.80e-02 g/l

分子性质

理化性质

• 溶解度: Freely soluble as disodium salt
• 疏水性(logP): 1.3

详细说明

DrugBank - DB01014

• Drug Groups: approved; investigational
• Description: 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.
• Indication: For the treatment of mildly to moderately active ulcerative colitis.
• Pharmacology: 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.
• 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
• Biotransformation: Cleaved in the colon via bacterial azoreduction to 5–aminosalicylic acid (5–ASA) and 4–aminobenzoyl-beta-alanine, the inactive carrier moiety.
• Absorption: Low and variable, intact balsalazide is poorly absorbed systemically.
• Half Life: Half-life could not be determined.
• Protein Binding: ≥99%
• Elimination: The products of the azoreduction of this compound, 5-ASA and 4-aminobenzoyl-?-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.
• References: 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] ; Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• 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
• Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. Pubmed