Acetohexamide

  • CAT Number: I005705
  • CAS Number: 968-81-0
  • Molecular Formula: C15H20N2O4S
  • Molecular Weight: 324.4
  • Purity: ≥95%
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Acetohexamide is a first-generation sulfonylurea medication used to treat diabetes mellitus type 2; stimulate the pancreas to secrete insulin.

Catalog Number I005705
CAS Number 968-81-0
Molecular Formula

C15H20N2O4S

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
Reference

</br>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 </br>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 Article</br>3: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 Article</br>4:[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 </br>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 Article</br>6: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 </br>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 </br>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 </br>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 Article</br>10: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

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