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G2295

Sigma-Aldrich

Glimepiride

≥98% (HPLC), solid

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About This Item

Empirical Formula (Hill Notation):
C24H34N4O5S
CAS Number:
93479-97-1
Molecular Weight:
490.62
MDL number:
MFCD00878417
UNSPSC Code:
12352200
PubChem Substance ID:
24895093
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white

mp

212.2-214.5 °C

solubility

DMSO: >10 mg/mL

originator

Sanofi Aventis

storage temp.

room temp

SMILES string

CCC1=C(C)CN(C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)N[C@H]3CC[C@H](C)CC3)C1=O

InChI

1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-

InChI key

WIGIZIANZCJQQY-RUCARUNLSA-N

Gene Information

human ... ABCC8(6833) , KCNJ1(3758) , KCNJ11(3767)

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General description

Glimepiride is a class II biopharmaceutical second-generation sulfonylurea.

Application

Glimepiride has been used:
  • as a hypoglycemic drug to test its anti-diabetic functionality in human umbilical vein cells (HUVECs)
  • as a sulfonylurea ATP-sensitive potassium channel (KATP) channel inhibitor in breast cancer MDA-MB-231 cells
  • in glucose-stimulated insulin secretion (GSIS) assays of neonatal islet-like cell clusters (NICCs) to test its effect on insulin secretion

Glimepiride is currently used to treat type 2 diabetes.

Biochem/physiol Actions

Glimepiride is a potent blocker of cardiac KATP channels activated by pinacidil with an IC50 of 6.8 nM.
Glimepiride reduces blood glucose levels by stimulating the pancreatic β cells to secrete insulin hormone. It interacts with a 65-kD protein associated with β cells.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Li-Ping Wang et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 38(6), 2337-2347 (2016-05-21)
By inducing severe endothelial impairment, hypertension and diabetes are two leading causes of morbidity and mortality. Hypertensive patients with concomitant diabetes must take both antihypertensive and hypoglycaemic medications, for which there is a lack of experimental and clinical guidelines. This
A REVIEW ARTICLE ON GLIMEPERIDE: AN ORAL HYPOGLYCAEMIC DRUG
Tiwari A, et al.
International Journal of Advanced Research , 4, 920-927 (2016)
W Rathmann et al.
Diabetes, obesity & metabolism, 15(1), 55-61 (2012-08-07)
To investigate therapy persistence, frequency of hypoglycaemia and macrovascular outcomes among type 2 diabetes patients with dipeptidyl peptidase-4 (DPP-4) inhibitors (DPP-4) and sulphonylureas (SU). Data from 19,184 DPP-4 (mean age: 64 years; 56% males) and 31,110 SU users (69 years;
William T Cefalu et al.
Lancet (London, England), 382(9896), 941-950 (2013-07-16)
Sodium-glucose cotransporter 2 (SGLT2) inhibitors improve glycaemia in patients with type 2 diabetes by enhancing urinary glucose excretion. We compared the efficacy and safety of canagliflozin, an SGLT2 inhibitor, with glimepiride in patients with type 2 diabetes inadequately controlled with
Thomas M Bodenstine et al.
FEBS letters, 586(1), 27-31 (2011-11-29)
Gap junctional intercellular communication (GJIC) regulates cellular homeostasis by propagating signaling molecules, exchanging cellular metabolites, and coupling electrical signals. In cancer, cells exhibit altered rates of GJIC which may play a role in neoplastic progression. K(ATP) channels help maintain membrane
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