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

• ChemBase编号: 938
• 分子式: C21H27N5O4S
• 平均质量: 445.53518
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide
• IUPAC传统名: glipizide; N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide
• 商标名: 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
• 别名: 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; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 4.3202024
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 0.6544149
• LogD (pH = 7.4): 0.48646381
• Log P: 1.4266123
• 摩尔折射率: 115.6178 cm^3
• 极化性: 45.127144 Å^3
• 极化表面积: 130.15 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.83
• LOG S: -4.43
• 溶解度: 1.64e-02 g/l

分子性质

理化性质

• 溶解度: 37.2 mg/L; DMSO; DMSO: soluble48 mg/mL; Ethanol; methanol: soluble1.9 mg/mL
• 外观: white solid; White Solid
• 熔点: 200-209°C; 208-209°C
• 疏水性(logP): 2.5

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: YS7640000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... KCNJ1(3758)
• 生物活性机理: Potassium channels (KATP) blocker

产品相关信息

• 级别: Selectophore™
• 成盐信息: Free Base
• 应用领域: Antidiabetic drug; Antihyperglycaemic agent
• Empirical Formula (Hill Notation): C21H27N5O4S

详细说明

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
请访问 传感器应用门户网站 了解更多信息。
Other Notes
EDTA 的电位滴定 Sm(III) 的指示电极1
法律信息
Selectophore 商标 Sigma-Aldrich GmbH

Toronto Research Chemicals - G410225

A sulfonylurea hypoglycemic agent. Used as an antidiabetic.

参考文献

• 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