Glisoxepide

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Glisoxepide
Glisoxepide.svg
Glisoxepide molecule ball.png
Names
Preferred IUPAC name
N-[2-(4-{[(Azepan-1-yl)carbamoyl]sulfamoyl}phenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.042.329 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C20H27N5O5S/c1-15-14-18(23-30-15)19(26)21-11-10-16-6-8-17(9-7-16)31(28,29)24-20(27)22-25-12-4-2-3-5-13-25/h6-9,14H,2-5,10-13H2,1H3,(H,21,26)(H2,22,24,27) Yes check.svgY
    Key: ZKUDBRCEOBOWLF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C20H27N5O5S/c1-15-14-18(23-30-15)19(26)21-11-10-16-6-8-17(9-7-16)31(28,29)24-20(27)22-25-12-4-2-3-5-13-25/h6-9,14H,2-5,10-13H2,1H3,(H,21,26)(H2,22,24,27)
    Key: ZKUDBRCEOBOWLF-UHFFFAOYAG
  • O=C(NCCc1ccc(cc1)S(=O)(=O)NC(=O)NN2CCCCCC2)c3noc(c3)C
Properties
C20H27N5O5S
Molar mass 449.52388 g/mol
Pharmacology
A10BB11 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glisoxepide (INN) is an orally available anti-diabetic drug from the group of sulfonylureas. [1] It belongs to second-generation sulfonylureas. [2]

Synthesis

Thieme Synthesis: Patent: Glisoxepide synthesis.svg
Thieme Synthesis: Patent:

Amide formation between 5-Methylisoxazole-3-Carboxylic Acid [3405-77-4] (1) and 4-(2-Aminoethyl)benzenesulfonamide [35303-76-5] (2) gives 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]-1,2-oxazole-3-carboxamide [24477-36-9] (3). Reaction with methyl chloroformate gives [24489-02-9] (4). Treatment with 1-aminoazepane [5906-35-4] (5) completes the synthesis of glisoxepide (6).

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References

  1. Haupt E, Köberich W, Beyer J, Schöffling K (December 1971). "Pharmacodynamic aspects of tolbutamide, glibenclamide, glibornuride and glisoxepide. I. Dose response relations and repeated administration in diabetic subjects". Diabetologia. 7 (6): 449–54. doi: 10.1007/bf01212061 . PMID   5004178.
  2. Loubatières, A; Ribes, G; Mariani, MM; Alric, R (1973). "Pharmacological Comparison Between Tolbutamide and Two Second Generation Hypoglycemic Sulfonylureas (Glibenclamide and Glisoxepide)". Acta Diabetologica Latina. 10 (2): 261–82. doi:10.1007/bf02590661. PMID   4200420.
  3. Plümpe H, Horstmann H, Puls W. [Isoxazolecarboxamidoalkylbenzolesulfonylurea, -semicarbazide and -aminopyrimidine as well as related compounds and their blood sugar reducing activity]. Arzneimittelforschung. 1974;24:363-74. PMID: 4408067.
  4. ZA6806886 corresponding to Hans Plumpe, Walter Puls, U.S. Patent 3,668,215 (1972 to Bayer Ag).