N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide

• ChemBase ID: 938
• Molecular Formular: C21H27N5O4S
• Molecular Mass: 445.53518
• Monoisotopic Mass: 445.17837537
• SMILES: S(=O)(=O)(NC(=O)NC1CCCCC1)c1ccc(CCNC(=O)c2ncc(nc2)C)cc1
• Canonical SMILES: Cc1ncc(nc1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1
• InChI: InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
• InChIKey: ZJJXGWJIGJFDTL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide
• IUPAC Traditional name: glipizide; N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide
• Brand Name: Aldiab; Digrin; Dipazide; Glibenese; Glibetin; Glican; Glide; Glidiab; Glipid; Glipizide Extended-Release Tablets; Gluco-Rite; Glucolip; Glucotrol; Glucotrol XL; Glucozide; Glupitel; Glupizide; Glyde; Melizide; Metaglip; Mindiab; Minidab; Minidiab; Minodiab; Napizide; Ozidia; Sucrazide
• Synonyms: Glipizida [INN-Spanish]; Glipizidum [INN-Latin]; Glydiazinamide; Glipizide; Glipizide; N-[2-[4[[[(Cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methylpyrazinecarboxamide; 1-Cyclohexyl-3-[[p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea; Aldiab; Digrin; Dipazide; Glibenese; Glibetin; Glican; Glidiab; Glipid; Glipizid; Gluco-Rite; Glucolip; Glucozide; Glupitel; Glupizid; Napizide; Ozidia; Semiglynase; Sucrazide; TK 1320; Minodiab; Glucotrol XL; Glucotrol; N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-5-methylpyrazine-2-carboxamide; 1-Cyclohexyl-3-{4-[2-(5-methylpyrazine-2-carboxamido)ethyl]phenylsulfonyl}urea; Glipizide; Samarium(III) ionophore I; 1-环己基-3-{4-[2-(5-甲基吡嗪-2-甲酰胺基)乙基]苯磺酰基}脲; 格列吡嗪; 格列吡嗪; 钐(III) 离子载体 I

Database IDs

• CAS Number: 29094-61-9
• EC Number: 249-427-6
• MDL Number: MFCD00072159
• PubChem SID: 24858438; 160964401; 24277839; 46505865
• PubChem CID: 3478

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3202024
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.6544149
• LogD (pH = 7.4): 0.48646381
• Log P: 1.4266123
• Molar Refractivity: 115.6178 cm^3
• Polarizability: 45.127144 Å^3
• Polar Surface Area: 130.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.83
• LOG S: -4.43
• Solubility (Water): 1.64e-02 g/l

PROPERTIES

Physical Property

• Solubility: 37.2 mg/L; DMSO; DMSO: soluble48 mg/mL; Ethanol; methanol: soluble1.9 mg/mL
• Apperance: white solid; White Solid
• Melting Point: 200-209°C; 208-209°C
• Hydrophobicity(logP): 2.5

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: YS7640000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... KCNJ1(3758)
• Mechanism of Action: Potassium channels (KATP) blocker

Product Information

• Grade: Selectophore™
• Salt Data: Free Base
• Application(s): Antidiabetic drug; Antihyperglycaemic agent
• Empirical Formula (Hill Notation): C21H27N5O4S

DETAILS

MP Biomedicals - 02159797

An ATP-dependent potassium channel blocker.

DrugBank - DB01067

• Drug Groups: approved
• Description: An oral hypoglycemic agent which is rapidly absorbed and completely metabolized. [PubChem]
• Indication: For use as an adjunct to diet for the control of hyperglycemia and its associated symptomatology in patients with non-insulin-dependent diabetes mellitus (NIDDM; type II), formerly known as maturity-onset diabetes, after an adequate trial of dietary therapy has proved unsatisfactory.
• Pharmacology: Glipizide, a second-generation sulfonylurea, is used with diet to lower blood glucose in patients with diabetes mellitus type II. The primary mode of action of glipizide in experimental animals appears to be the stimulation of insulin secretion from the beta cells of pancreatic islet tissue and is thus dependent on functioning beta cells in the pancreatic islets. In humans glipizide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. In man, stimulation of insulin secretion by glipizide in response to a meal is undoubtedly of major importance. Fasting insulin levels are not elevated even on long-term glipizide administration, but the postprandial insulin response continues to be enhanced after at least 6 months of treatment. Some patients fail to respond initially, or gradually lose their responsiveness to sulfonylurea drugs, including glipizide.
• Toxicity: The acute oral toxicity was extremely low in all species tested (LD50 greater than 4 g/kg). Overdosage of sulfonylureas including glipizide can produce hypoglycemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. The major metabolites of glipizide are products of aromatic hydroxylation and have no hypoglycemic activity. A minor metabolite which accounts for less than 2% of a dose, an acetylaminoethyl benzine derivatives, is reported to have 1/10 to 1/3 as much hypoglycemic activity as the parent compound.
• Absorption: Gastrointestinal absorption is uniform, rapid, and essentially complete.
• Half Life: 2-5 hours
• Protein Binding: 98-99%, primarily to albumin.
• Elimination: The primary metabolites are inactive hydroxylation products and polar conjugates and are excreted mainly in the urine.
• Distribution: * 11 L
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1715

Research Area: Endocrinology
Biological Activity:
Glipizide(Glucotrol) is used to treat high blood sugar levels caused by a type of diabetes mellitus called type 2 diabetes. Glipizide belongs to a class of drugs called sulfonylureas. It stimulates the release of insulin from the pancreas, directing your body to store blood sugar. This helps lower blood sugar and restores the way you use food to make energy. [1, 2]

Sigma Aldrich - G117

Biochem/physiol Actions
ATP-dependent K+ channel blocker.

Sigma Aldrich - 30553

General description
Visit our Sensor Applications portal to learn more.
Other Notes
Indicator electrode for the potentiometric determination of Sm(III) with EDTA1
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

Toronto Research Chemicals - G410225

A sulfonylurea hypoglycemic agent. Used as an antidiabetic.

REFERENCES

• http://en.wikipedia.org/wiki/Glipizide
• Ambrogi, et al.: Arzneimittel-Forsch., 21, 200 (1971)
• Fuccella, et al.: J. Clin. Pharmacol., 13, 68 (1971)
• Brogden, R.N., et al.: Drugs, 18, 329 (1971)
• Lebovitz, H.E., et al.: Pharmacother., 5, 63 (1985)
• Ambrogi, V. et al., Arzneim.-Forsch., 1971, 21, 200; 208; 215; 242, (pharmacol, synth)
• Brogden, R.N. et al., Drugs, 1979, 18, 329, (rev)
• Lebovitz, H.E. et al., Am. J. Med., 1983, 75, 46; 55, (revs)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6268, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 280