3-cyclohexyl-1-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea

• ChemBase ID: 1120
• Molecular Formular: C27H33N3O6S
• Molecular Mass: 527.63242
• Monoisotopic Mass: 527.20900679
• SMILES: S(=O)(=O)(NC(=O)NC1CCCCC1)c1ccc(CCN2C(=O)C(c3c(C2=O)cc(OC)cc3)(C)C)cc1
• Canonical SMILES: COc1ccc2c(c1)C(=O)N(C(=O)C2(C)C)CCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1
• InChI: InChI=1S/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)
• InChIKey: LLJFMFZYVVLQKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-cyclohexyl-1-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea; 1-cyclohexyl-3-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea
• IUPAC Traditional name: 3-cyclohexyl-1-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]benzenesulfonyl}urea; gliquidone; 1-cyclohexyl-3-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea
• Brand Name: Glurenorm
• Synonyms: Gliquidone; Glurenor; Glurenorm; Gliquidone

Database IDs

• CAS Number: 33342-05-1
• PubChem SID: 160964583; 46508425
• PubChem CID: 91610

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3201785
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.3635724
• LogD (pH = 7.4): 3.19562
• Log P: 4.1357684
• Molar Refractivity: 139.4806 cm^3
• Polarizability: 54.35235 Å^3
• Polar Surface Area: 121.88 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.59
• LOG S: -5.38
• Solubility (Water): 2.20e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0022 mg/mL [Predicted by ALOGPS]
• Hydrophobicity(logP): 4.5

Pharmacology Properties

• Target: Others
• Mechanism of Action: Potassium channels (KATP) blocker

Product Information

• Salt Data: Free Base
• Application(s): Antidiabetic agent; Antihyperglycaemic agent

DETAILS

DrugBank - DB01251

• Drug Groups: approved
• Description: Gliquidone is an anti-diabetic drug in the sulfonylurea class. It is used in the treatment of diabetes mellitus type 2. It is an ATP-dependent K+ (KATP) channel blocker. This block causes a depolarization which leads to activation of voltage-dependent Ca channels and Ca2+ influx, and eventually increases insulin release.
• Indication: Used in the treatment of diabetes mellitus type 2.
• Pharmacology: Gliquidone is an anti-diabetic drug in the sulfonylurea class. In patients with diabetes mellitus, there is a deficiency or absence of a hormone manufactured by the pancreas called insulin. Insulin is the main hormone responsible for the control of sugar in the blood. Gliquidone is an antidiabetic medication which is used in those patients with adult maturity onset or non-insulin dependent diabetes (NIDDM). It works by lowering blood sugar levels by stimulating the production and release of insulin from the pancreas. It also promotes the movement of sugar from the blood into the cells in the body which need it.
• Affected Organisms: Humans and other mammals
• Half Life: The mean terminal half-life was approximately 8 hours (range 5.7-9.4 hours)
• External Links: Wikipedia

REFERENCES

• Ger. Pat., 1971, 2 011 126; CA, 76, 14359c, (synth)
• Kopitar, Z. et al., Arzneim.-Forsch., 1975, 25, 1455; 1933, (metab)
• Hopkins, S.J. et al., Drugs of Today (Barcelona), 1980, 16, 47, (rev, pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 280