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药品详细

Acetohexamide(醋磺)

化学结构式图
中文名
醋磺
英文名
Acetohexamide
分子式
C15H20N2O4S
化学名
1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea
分子量
Average: 324.395
Monoisotopic: 324.114377828
CAS号
968-81-0
ATC分类
A10B Oral Blood Glucose Lowering Drugs, Excl. Insulins
药物类型
small molecule
阶段
approved
商品名
Cyclamide;Dimelin;Dimelor;Dymelor;Gamadiabet;Hypoglicil;Metaglucina;Minoral;Ordimel;Tsiklamid;
同义名
Acetohexamid;
基本介绍

A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. [PubChem]

生产厂家
  • Barr laboratories inc
  • Eli lilly industries inc
  • Usl pharma inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Sulfonylureas
Substructures
  • Sulfonylureas
  • Sulfonyls
  • Benzene and Derivatives
  • Ureas and Derivatives
  • Benzenesulfonamides
  • Aromatic compounds
  • Sulfonamides
  • Benzoyl Derivatives
  • Acetophenones and Derivatives
  • Ketones
适应症
Diabetes 糖尿病;
药理
Indication Used in the management of diabetes mellitus type 2 (adult-onset).
Pharmacodynamics Acetohexamide is an intermediate-acting, first-generation oral sulfonylurea. It lowers blood sugar by stimulating the pancreatic beta cells to secrete insulin and by helping the body use insulin efficiently. The pancreas must produce insulin for this medication to work. Acetohexamide has one-third the potency of chlorpropamide, and twice the potency of tolbutamide; however, similar hypoglycemic efficacy occurs with equipotent dosage of sulfonylureas.
Mechanism of action Sulfonylureas such as acetohexamide bind to an ATP-dependent K+ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing outflux of potassium, which causes the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of (pro)insulin.
Absorption Rapidly absorbed from the GI tract.
Volume of distribution Not Available
Protein binding 90%
Metabolism
Extensively metabolized in the liver to the active metabolite hydroxyhexamide, which exhibits greater hypoglycemic potency than acetohexamide. Hydroxyhexamide is believed to be responsible for prolonged hypoglycemic effects.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Acetohexamide
    		Hydroxyhexamide Details
    Route of elimination Not Available
    Half life Elimination half-life of the parent compound is 1.3 hours and the elimination half-life of the active metabolite is approximately 5-6 hours.
    Clearance Not Available
    Toxicity Oral, rat LD50: 5 gm/kg; Oral, mouse LD50: >2500 mg/kg. Symptoms of an acetohexamide overdose include hunger, nausea, anxiety, cold sweats, weakness, drowsiness, unconsciousness, and coma.
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 188-190 °C Not Available
    water solubility 3430 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
    logP 2.44 SANGSTER (1993)
    logS -2.06 ADME Research, USCD
    Predicted Properties
    Property Value Source
    water solubility 4.83e-02 g/l ALOGPS
    logP 1.72 ALOGPS
    logP 1.81 ChemAxon
    logS -3.8 ALOGPS
    pKa (strongest acidic) 4.31 ChemAxon
    pKa (strongest basic) -7.4 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 4 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 92.34 ChemAxon
    rotatable bond count 3 ChemAxon
    refractivity 82.77 ChemAxon
    polarizability 33.97 ChemAxon
    药物相互作用
    Drug Interaction
    Acebutolol Acebutolol may decrease symptoms of hypoglycemia and increase the time required for the body to compensate for hypoglycemia.
    Acetylsalicylic acid Acetylsalicylic acid increases the effect of sulfonylurea, acetohexamide.
    Atenolol The beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
    Betaxolol The beta-blocker, betaxolol, may decrease symptoms of hypoglycemia.
    Bisoprolol The beta-blocker, bisoprolol, may decrease symptoms of hypoglycemia.
    Carteolol The beta-blocker, carteolol, may decrease symptoms of hypoglycemia.
    Carvedilol The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
    Chloramphenicol Chloramphenicol may increase the effect of sulfonylurea, acetohexamide.
    Clofibrate Clofibrate may increase the effect of sulfonylurea, acetohexamide.
    Dicumarol Dicumarol may increase the effect of sulfonylurea, acetohexamide.
    Esmolol The beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
    Labetalol The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
    Metoprolol The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
    Nadolol The beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
    Oxprenolol The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
    Phenylbutazone Phenylbutazone may increase the effect of acetohexamide.
    Pindolol The beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
    Practolol The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
    Propranolol The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
    Rifampin Rifampin may decrease the effect of sulfonylurea, acetohexamide.
    Sotalol The beta-blocker, sotalol, may decrease symptoms of hypoglycemia.
    Timolol The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
    食物相互作用
    • Avoid alcohol.
    • Take without regard to meals.

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