Glisoxepide
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MedKoo CAT#: 317974

CAS#: 25046-79-1

Description: Glisoxepide is a second-generation sulfonylurea with antihyperglycemic activity. Like other second-generation compounds, glisoxepide exerts greater binding affinity than the first-generation compounds. Glisoxepide shows peroxisome proliferator-activated receptor gamma agonistic activity, has a short half-life and is excreted in both the bile and urine.

Chemical Structure

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Glisoxepide
CAS# 25046-79-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317974
Name: Glisoxepide
CAS#: 25046-79-1
Chemical Formula: C20H27N5O5S
Exact Mass: 449.17
Molecular Weight: 449.239
Elemental Analysis: C, 53.44; H, 6.05; N, 15.58; O, 17.80; S, 7.13

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Synonym: Glisoxepide; Glisoxepid; Pro-Diaban; Glisepin; Glisoxepida [Spanish]; Glisoxepida; BS 4231; BS-4231; glisoxepid; glisoxepide; Pro-diaban; RP 22410; RP-22410;

IUPAC/Chemical Name: N-[2-[4-(azepan-1-ylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide

InChi Key: ZKUDBRCEOBOWLF-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: CC1=CC(=NO1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NN3CCCCCC3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Glisoxepide, a sulphonamide derivative, is an orally available nonselective K(ATP) channel blocker, with antihyperglycemic activity and cardiovascular regulation effect.
In vitro activity: Bepridil (10 microM) completely inhibited the pinacidil-induced Kir6.2+SUR2A channel current expressed in HEK 293 cells. Bepridil reversibly oxidized the flavoprotein and increased mitochondrial matrix volume in a concentration-dependent manner. Furthermore, bepridil significantly attenuated the ouabain-induced increase of [Ca(2+)](m). Pretreatment with bepridil for 5 min before ischemia improved the recovery of developed tension measured after 60 min of reperfusion. These effects of bepridil were abolished by the mitoK(ATP) channel blocker 5-hydroxydecanoate (500 microM) and by the nonselective K(ATP) channel blocker glisoxepide (10 microM). Reference: J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. https://pubmed.ncbi.nlm.nih.gov/16174795/
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 449.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Sato T, Costa AD, Saito T, Ogura T, Ishida H, Garlid KD, Nakaya H. Bepridil, an antiarrhythmic drug, opens mitochondrial KATP channels, blocks sarcolemmal KATP channels, and confers cardioprotection. J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. doi: 10.1124/jpet.105.094029. Epub 2005 Sep 20. PMID: 16174795. 2. Fückel D, Petzinger E. Interaction of sulfonylureas with the transport of bile acids into hepatocytes. Eur J Pharmacol. 1992 Mar 31;213(3):393-404. doi: 10.1016/0014-2999(92)90628-h. PMID: 1618280.
In vitro protocol: 1. Sato T, Costa AD, Saito T, Ogura T, Ishida H, Garlid KD, Nakaya H. Bepridil, an antiarrhythmic drug, opens mitochondrial KATP channels, blocks sarcolemmal KATP channels, and confers cardioprotection. J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. doi: 10.1124/jpet.105.094029. Epub 2005 Sep 20. PMID: 16174795. 2. Fückel D, Petzinger E. Interaction of sulfonylureas with the transport of bile acids into hepatocytes. Eur J Pharmacol. 1992 Mar 31;213(3):393-404. doi: 10.1016/0014-2999(92)90628-h. PMID: 1618280.
In vivo protocol: TBD

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1: Gutsche H, Losert W. [Clinico-pharmacological studies on the duration of
action of the oral antidiabetic drug glisoxepide (author's transl)].
Arzneimittelforschung. 1977;27(9):1719-26. German. PubMed PMID: 336058.


2: Blumenbach L, Kiesselbach N, Lehnert J. [Further results of a multi-centre
clinical trial with the oral antidiabetic drug glisoxepide (author's transl)].
Arzneimittelforschung. 1976;26(5):931-43. German. PubMed PMID: 786303.


3: Lehnert J, Kiesselbach NH, Blumenbach L. [Multicentric clinical proof of a new
oral antidiabetic glisoxepide (BS 4231). 1. Establishment of proof and methods].
Arzneimittelforschung. 1974 Mar;24(0):433-7. German. PubMed PMID: 4603693.


4: Puls W, Losert W, Loge O, Schillinger E, Keup U, Kroneberg G. [The
pharmacology of glisoxepide, a new oral antidiabetic]. Arzneimittelforschung.
1974 Mar;24(0):375-92. German. PubMed PMID: 4408136.


5: Schlossmann K. [Protein binding of glisoxepide and its influence on the
protein binding of phenprocoumon]. Arzneimittelforschung. 1974 Mar;24(0):392-7.
German. PubMed PMID: 4408096.


6: Birk W, Petrides P. [Behavior of serum insulin under the influence of
glisoxepide with and without butylbiguanide]. Arzneimittelforschung. 1974
Mar;24(0):425-9. German. PubMed PMID: 4408033.


7: Haupt E, Beyer J, Schöffling K. [Pharmacologic study with glisoxepide and
other blood sugar reducing sulfonamide derivatives in metabolically healthy
subjects and diabetics]. Arzneimittelforschung. 1974 Mar;24(0):418-25. German.
PubMed PMID: 4211557.


8: Loubatiéres A, Mariani MM, Ribes G, Alric R. Pharmacological comparison
between tolbutamide and two second generation hypoglycemic sulfonylureas
(glibenclamide and glisoxepide). Acta Diabetol Lat. 1973 Mar-Apr;10(2):261-82.
PubMed PMID: 4200675.


9: Loubatières AL, Ribes G, Loubatières-Mariani MM. [Effect of glycemia level on
insulin secretion caused by an hypoglycemic sulfamide (glisoxepide) in dogs]. C R
Seances Soc Biol Fil. 1972;166(8):1047-50. French. PubMed PMID: 4573746.


10: Haupt E, Köberich W, Beyer J, Schöffling K. Pharmacodynamic aspects of
tolbutamide, glibenclamide, glibornuride, and glisoxepide. II. Repeated
administration in combination with glucose. Diabetologia. 1971 Dec;7(6):455-60.
PubMed PMID: 5004179.


11: Irsigler K, Ogris E, Steinhardt T, Brändle J, Regal H, Zdolsek I. [Comparison
of glibenclamide, gliquidone, glisoxepide and placebo in maturity onset diabetics
of differing degrees of severity (author's transl)]. Wien Klin Wochenschr. 1979
Aug 31;91(16):541-50. German. PubMed PMID: 115159.


12: Hausmann L, Schumann G, Kaffarnik H. [Insulin and pro-insulin secretion
following intravenous administration of tolbutamide, glisoxepide and
glibenclamide]. Arzneimittelforschung. 1978;28(1):83-6. German. PubMed PMID:
415745.


13: Happ J, Beyer J, Ulreich F, Schöffling K, Krause U, Frönlich A. [Glisoxepide
treatment in maturity-onset diabetics (author's transl)]. Dtsch Med Wochenschr.
1976 Nov 5;101(45):1643-6. German. PubMed PMID: 1033056.


14: Nieuweboer B, Gabriel D, Lübke K. A method for radioimmunological assay of
glisoxepide (author's transl). Arzneimittelforschung. 1976;26(9):1633-6. German.
PubMed PMID: 1036690.


15: Söling HD, Seck A. Precursor specific inhibition of hepatic gluconeogenesis
by glisoxepide, an inhibitor of the L-aspartate/L-glutamate antiport system. FEBS
Lett. 1975 Mar 1;51(1):52-9. PubMed PMID: 235462.


16: Kiesselbach NH, Blumenbach L, Lehnert J. [Multicentric clinical proof of a
new oral antidiabetic glisoxepide (BS 4231). 3. Results of tolerance tests].
Arzneimittelforschung. 1974 Mar;24(0):447-52. German. PubMed PMID: 4603694.


17: Blumenbach L, Kiesselbach NH, Lehnert J. [Multicentric clinical proof of a
new oral antidiabetic glisoxepide (BS 4231). II. Proof of activity in the
management of adult onset diabetes]. Arzneimittelforschung. 1974
Mar;24(0):437-46. German. PubMed PMID: 4603692.


18: Petzoldt R, Riedesel G, Ramrath M, Grabs V, Haupt E, Schwedes U, Ewald W,
Beyer J, Schöffling K. [Clinical experience with the blood sugar reducing
sulfonamide derivative glisoxepide]. Arzneimittelforschung. 1974
Mar;24(0):429-32. German. PubMed PMID: 4603399.


19: Tettenborn D. [The toxicology of glisoxepide, a new oral antidiabetic.
Results of animal studies]. Arzneimittelforschung. 1974 Mar;24(0):409-18. German.
PubMed PMID: 4408138.


20: Speck U, Mützel W, Kolb KH, Acksteiner B, Schulze PE. [Pharmacokinetics and
metabolite spectrum of glisoxepide in humans]. Arzneimittelforschung. 1974
Mar;24(0):404-9. German. PubMed PMID: 4408089.