Acetohexamide

• CAT Number: I005705
• CAS Number: 968-81-0
• Molecular Formula: C15H20N2O4S
• Molecular Weight: 324.40
• Purity: ≥95%
• Solubility: DMSO: 39 mg/mL
• Storage: 3 years -20C powder
• 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)
• InChIKey: VGZSUPCWNCWDAN-UHFFFAOYSA-N
• SMILES: CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2CCCCC2

Acetohexamide (Cat No.: I005705) is a first-generation sulfonylurea oral hypoglycemic agent used to manage type 2 diabetes mellitus. It lowers blood glucose by stimulating insulin release from pancreatic beta cells and enhancing peripheral insulin sensitivity. Acetohexamide is metabolized in the liver to active compounds, contributing to its prolonged hypoglycemic effect. Although largely replaced by newer agents, it remains important in pharmacological research on sulfonylureas and insulin secretion mechanisms. Its historical role provides insight into the evolution of diabetes treatment strategies.

Reference

1:Crystallization of a new polymorph of acetohexamide from 2-hydroxybutyl-β-cyclodextrin solution: form VI with a high aqueous solubility. Aldawsari H, Altaf A, Banjar ZM, Iohara D, Nakabayashi M, Anraku M, Uekama K, Hirayama F.Int J Pharm. 2013 Sep 10;453(2):315-21. doi: 10.1016/j.ijpharm.2013.06.026. Epub 2013 Jun 21. PMID: 23796835 2:In vitro inhibition of breast cancer spheroid-induced lymphendothelial defects resembling intravasation into the lymphatic vasculature by acetohexamide, isoxsuprine, nifedipin and proadifen. Kretschy N, Teichmann M, Kopf S, Atanasov AG, Saiko P, Vonach C, Viola K, Giessrigl B, Huttary N, Raab I, Krieger S, Jäger W, Szekeres T, Nijman SM, Mikulits W, Dirsch VM, Dolznig H, Grusch M, Krupitza G.Br J Cancer. 2013 Feb 19;108(3):570-8. doi: 10.1038/bjc.2012.580. Epub 2013 Jan 8. PMID: 23299527 Free PMC Article3:Chromatographic analysis of acetohexamide binding to glycated human serum albumin. Joseph KS, Anguizola J, Jackson AJ, Hage DS.J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 15;878(28):2775-81. doi: 10.1016/j.jchromb.2010.08.021. Epub 2010 Aug 21. PMID: 20829128 Free PMC Article4:[Studies for analyzing the prohibited ingredients such as acetohexamide in cosmetics]. Tokunaga H, Uchino T.Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 2005;(123):19-22. Japanese. PMID: 16541746 5:Differential pharmacokinetics of acetohexamide in male Wistar-Imamichi and Sprague-Dawley rats: role of microsomal carbonyl reductase. Imamura Y, Shimada H.Biol Pharm Bull. 2005 Jan;28(1):185-7. PMID: 15635190 Free Article6:Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats. Imamura Y, Kaneko M, Takada H, Otagiri M, Shimada H, Akita H.Comp Biochem Physiol C Toxicol Pharmacol. 2002 Dec;133(4):587-92. PMID: 12458186 7:Cadmium exposure decreases androgen-dependent metabolism of acetohexamide in liver microsomes of male rats through its testicular toxicity. Shimada H, Yamaguchi S, Murata H, Otagiri M, Imamura Y.Arch Toxicol. 2002 Feb;76(1):8-12. Epub 2001 Dec 20. PMID: 11875619 8:Hypoglycemic effect of S(-)-hydroxyhexamide, a major metabolite of acetohexamide, and its enantiomer R(+)-hydroxyhexamide. Imamura Y, Sanai K, Seri K, Akita H.Life Sci. 2001 Sep 7;69(16):1947-55. PMID: 11693275 9:[Strain-, sex- and species-related differences of acetohexamide reductase and 20 beta-hydroxysteroid dehydrogenase activities in liver microsomes of experimental animals]. Imamura Y, Uchida A, Takada H, Otagiri M, Tsuchiya K.Yakugaku Zasshi. 2001 Jan;121(1):85-91. Japanese. PMID: 11201165 Free Article10:Catalytic properties for naphthoquinones and partial primary structure of rabbit heart acetohexamide reductase. Imamura Y, Koga T, Uriu Y, Otagiri M, Satoh K, Hara A.Biol Pharm Bull. 2000 Feb;23(2):155-8. PMID: 10706377