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Name: Acetohexamide
PubChem Compound ID: 1989
Description: A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide.
Molecular formula: C15H20N2O4S
Molecular weight: 324.396 g/mol
Benzenesulfonamide, 4-acetyl-N-[(cyclohexylamino)carbonyl]-; C06806; NCGC00016555-01; 1-(p-Acetylbenzenesulfonyl)-3-cyclohexylurea; Ordimel; CCRIS 4; BRN 2225115; Acetohexamid; EINECS 213-530-4; D00219.
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Name: Acetohexamide
Name (isomeric): DB00414
Drug Type: small molecule
Description: A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide.
Brand: Tsiklamid, Ordimel, Minoral, Metaglucina, Cyclamide, Hypoglicil, Dimelor, Dimelin, Gamadiabet, Dymelor
Category: Hypoglycemic Agents, Sulfonylureas
CAS number: 968-81-0
Indication: Used in the management of diabetes mellitus type 2 (adult-onset).
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 potenc...
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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 in...
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Absorption: Rapidly absorbed from the GI tract.
Protein binding: 90%
Biotransformation: 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.
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.
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
Food interaction:
Avoid alcohol.
Take without regard to meals.
Drug interaction:
PindololThe beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
OxprenololThe beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
NadololThe beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
ChloramphenicolChloramphenicol may increase the effect of sulfonylurea, acetohexamide.
PropranololThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
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