Tìm theo
Acetohexamide
Các tên gọi khác (8 ) :
  • 1-((p-Acetylphenyl)sulfonyl)-3-cyclohexylurea
  • 1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
  • Acetohexamid
  • Acetohexamida
  • Acétohexamide
  • Acetohexamide
  • Acetohexamidum
  • N-(p-Acetylphenylsulfonyl)-N'-cyclohexylurea
Insulin và nhóm Thuốc hạ đường huyết
Thuốc Gốc
Small Molecule
CAS: 968-81-0
ATC: A10BB31
ĐG : Barr Pharmaceuticals
CTHH: C15H20N2O4S
PTK: 324.395
A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. Acetohexamide has been discontinued in the US market.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H20N2O4S
Phân tử khối
324.395
Monoisotopic mass
324.114377828
InChI
InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
InChI Key
InChIKey=VGZSUPCWNCWDAN-UHFFFAOYSA-N
IUPAC Name
1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea
Traditional IUPAC Name
1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea
SMILES
CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
Độ tan chảy
188-190 °C
Độ hòa tan
3430 mg/L (at 37 °C)
logP
2.44
logS
-2.06
pKa (strongest acidic)
4.31
pKa (Strongest Basic)
-7.4
PSA
92.34 Å2
Refractivity
82.77 m3·mol-1
Polarizability
33.97 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. Acetohexamide has been discontinued in the US market. 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.
Dược Động Học :
▧ Absorption :
Rapidly absorbed from the GI tract.
▧ 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.
▧ 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.
Độc Tính : 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.
Chỉ Định : Used in the management of diabetes mellitus type 2 (adult-onset).
Tương Tác Thuốc :
  • 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.
  • Dicoumarol 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.
  • Rifampicin 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.
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty : Watson
    Sản phẩm biệt dược : Acetohexamide
  • Công ty : Shionogi Seiyaku
    Sản phẩm biệt dược : Dimelin
  • Công ty : Lilly
    Sản phẩm biệt dược : Dymelor
  • Công ty : Salvat
    Sản phẩm biệt dược : Gamadiabet
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00414
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=1989
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505821
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06806
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00219
ChemSpider
http://www.chemspider.com/Chemical-Structure.1912.html
PharmGKB
http://www.pharmgkb.org/drug/PA164777011
Wikipedia
http://en.wikipedia.org/wiki/Acetohexamide
Drugs.com
http://www.drugs.com/mtm/acetohexamide.html
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