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

• ChemBase ID: 1119
• Molecular Formular: C14H10N2O6
• Molecular Mass: 302.239
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
• IUPAC Traditional name: olsalazine
• Brand Name: Dipentum
• Synonyms: Olsalazine sodium; Olsalazine

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.926956
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.11579686
• LogD (pH = 7.4): -2.4937713
• Log P: 4.3871746
• Molar Refractivity: 78.8512 cm^3
• Polarizability: 27.597473 Å^3
• Polar Surface Area: 139.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -3.59
• Solubility (Water): 7.81e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.0817 mg/mL [Predicted by ALOGPS]
• Hydrophobicity(logP): 2.3

DETAILS

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