Glimepiride | CAS#93479-97-1

Glimepiride
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317971

CAS#: 93479-97-1

Description: Glimepiride is a third generation sulfonylurea compound, which increases the release of insulin from pancreatic beta cells. In addition, glimepiride increases the activity of intracellular insulin receptors. Glimepiride increases osteoblast proliferation and differentiation, which is thought to be related to its ability to activate the PI3K and Akt pathway. Furthermore, Glimepiride enhances intrinsic peroxisome proliferator-activated receptor γ activity. Glimepiride also increases protein expression of glucose transports 1 and 4, and is a potent KIR channel blocker.

Chemical Structure

Glimepiride

CAS# 93479-97-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317971
Name: Glimepiride
CAS#: 93479-97-1
Chemical Formula: C24H34N4O5S
Exact Mass: 490.22
Molecular Weight: 490.620
Elemental Analysis: C, 58.75; H, 6.99; N, 11.42; O, 16.31; S, 6.54

Price and Availability

Size	Price	Availability
200mg	USD 150	Ready to ship
500mg	USD 280	Ready to ship
1g	USD 350	Ready to ship
2g	USD 550	Ready to ship
5g	USD 950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Glimepiride; Amaryl; Amarel; Glimepirida; Glimepiridum; Hoechst brand of glimepiride; Lacer brand of glimepiride; Roname; HOE 490; HOE-490;

IUPAC/Chemical Name: 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide

InChi Key: WIGIZIANZCJQQY-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C

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

Certificate of Analysis:

View CoA: current batch, Lot#T8C05I15

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Glimepiride (Glimperide) is a medium-to-long acting sulfonylurea anti-diabetic compound with an ED50 of 182 μg/kg.
In vitro activity:	The effects of the sulphonylurea, glimepiride, currently used to treat type 2 diabetes, on ATP-sensitive K(+) (K(ATP)) currents of rat cardiac myocytes and on their cloned constituents Kir6.2 and SUR2A expressed in HEK 293 cells was investigated. Glimepiride blocked pinacidil-activated whole-cell K(ATP) currents of cardiac myocytes with an IC(50) of 6.8 nM, comparable to the potency of glibenclamide in these cells. Glimepiride blocked K(ATP) channels formed by co-expression of Kir6.2/SUR2A subunits in HEK 293 cells in outside-out excised patches with a similar IC(50) of 6.2 nM. Glimepiride was much less effective at blocking K(ATP) currents activated by either metabolic inhibition (MI) with CN(-) and iodoacetate or by the K(ATP) channel opener diazoxide in the presence of inhibitors of F(0)/F(1)-ATPase (oligomycin) and creatine kinase (DNFB). Thus 10 microM glimepiride blocked pinacidil-activated currents by >99%, MI-activated currents by 70% and diazoxide-activated currents by 82%. In inside-out patches from HEK 293 cells expressing the cloned K(ATP) channel subunits Kir6.2/SUR2A, increasing the concentration of ADP (1 - 100 microM), in the presence of 100 nM glimepiride, lead to significant increases in Kir6.2/SUR2A channel activity. However, over the range tested, ADP did not affect cloned K(ATP) channel activity in the presence of 100 nM glibenclamide. These results are consistent with the suggestion that ADP reduces glimepiride block of K(ATP) channels. These results show that glimepiride is a potent blocker of native cardiac K(ATP) channels activated by pinacidil and blocks cloned Kir6.2/SUR2A channels activated by ATP depletion with similar potency. However, glimepiride is much less effective when K(ATP) channels are activated by MI and this may reflect a reduction in glimepiride block by increased intracellular ADP. Reference: Br J Pharmacol. 2002 Jul;136(5):746-52. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/12086984/
In vivo activity:	The effect of glimepiride on fasting blood glucose, glucose tolerance, and insulin secretion was tested. It was also examined for the effect on glucagon, gluconeogenesis, and insulin sensitivity. Unexpectedly, glimepiride exposure in mice was associated with fasting hyperglycemia, glucose intolerance, and decreased insulin. There was no change in circulating glucagon levels or gluconeogenesis. The effect was dose-dependent, took effect by two weeks, and was reversed within three weeks after removal. Glimepiride elicited the same effects in all strains evaluated: four wild-type strains, as well as the transgenic Grn-/- and diabetic db/db mice. These findings suggest that the use of glimepiride as a hypoglycemic agent in mice should proceed with caution and may have broader implications about mouse models as a proxy to study the human pharmacopeia. Reference: J Diabetes Res. 2018 Oct 29;2018:1251345. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30510962/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	11.0	22.42

Preparing Stock Solutions

The following data is based on the product molecular weight 490.62 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.

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:
In vitro protocol:	1. Lawrence CL, Rainbow RD, Davies NW, Standen NB. Effect of metabolic inhibition on glimepiride block of native and cloned cardiac sarcolemmal K(ATP) channels. Br J Pharmacol. 2002 Jul;136(5):746-52. doi: 10.1038/sj.bjp.0704770. PMID: 12086984; PMCID: PMC1573398. 2. Liu F, Wang Y, Yan M, Zhang L, Pang T, Liao H. Glimepiride attenuates Aβ production via suppressing BACE1 activity in cortical neurons. Neurosci Lett. 2013 Dec 17;557 Pt B:90-4. doi: 10.1016/j.neulet.2013.10.052. Epub 2013 Oct 31. PMID: 24184877.
In vivo protocol:	1. Niedowicz DM, Özcan S, Nelson PT. Glimepiride Administered in Chow Reversibly Impairs Glucose Tolerance in Mice. J Diabetes Res. 2018 Oct 29;2018:1251345. doi: 10.1155/2018/1251345. PMID: 30510962; PMCID: PMC6231393. 2. Ishola IO, Akataobi OE, Alade AA, Adeyemi OO. Glimepiride prevents paraquat-induced Parkinsonism in mice: involvement of oxidative stress and neuroinflammation. Fundam Clin Pharmacol. 2019 Jun;33(3):277-285. doi: 10.1111/fcp.12434. Epub 2018 Dec 7. PMID: 30451327.

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1: Rizvi SM, Shaikh S, Naaz D, Shakil S, Ahmad A, Haneef M, Abuzenadah AM. Kinetics and Molecular Docking Study of an Anti-diabetic Drug Glimepiride as Acetylcholinesterase Inhibitor: Implication for Alzheimer's Disease-Diabetes Dual Therapy. Neurochem Res. 2016 Feb 17. [Epub ahead of print] PubMed PMID: 26886763.

2: Osborne C, West E, Nolan W, McHale-Owen H, Williams A, Bate C. Glimepiride protects neurons against amyloid-β-induced synapse damage. Neuropharmacology. 2016 Feb;101:225-36. doi: 10.1016/j.neuropharm.2015.09.030. Epub 2015 Oct 8. PubMed PMID: 26432105.

3: Tani S, Nagao K, Hirayama A. Differences between Mitiglinide/Voglibose Fixed-dose Combination and Glimepiride in Modifying Low-density Lipoprotein Heterogeneity in Japanese Type-2 Diabetic Patients: A Pilot Study. Drug Res (Stuttg). 2016 Feb;66(2):94-9. doi: 10.1055/s-0035-1549993. Epub 2015 May 26. PubMed PMID: 26011816.

4: Dungan KM, Weitgasser R, Perez Manghi F, Pintilei E, Fahrbach JL, Jiang HH, Shell J, Robertson KE. A 24-week Study to Evaluate the Efficacy and Safety of Once Weekly Dulaglutide Added on to Glimepiride in Type 2 Diabetes (AWARD-8). Diabetes Obes Metab. 2016 Jan 22. doi: 10.1111/dom.12634. [Epub ahead of print] PubMed PMID: 26799540.

5: Reginald-Opara JN, Attama A, Ofokansi K, Umeyor C, Kenechukwu F. Molecular interaction between glimepiride and Soluplus(®)-PEG 4000 hybrid based solid dispersions: Characterisation and anti-diabetic studies. Int J Pharm. 2015 Dec 30;496(2):741-50. doi: 10.1016/j.ijpharm.2015.11.007. Epub 2015 Nov 12. PubMed PMID: 26581773.

6: Giorgino F, Benroubi M, Sun JH, Zimmermann AG, Pechtner V. Efficacy and Safety of Once-Weekly Dulaglutide Versus Insulin Glargine in Patients With Type 2 Diabetes on Metformin and Glimepiride (AWARD-2). Diabetes Care. 2015 Dec;38(12):2241-9. doi: 10.2337/dc14-1625. Epub 2015 Jun 18. PubMed PMID: 26089386.

7: Kousoulakou H, Kalogeropoulou M, Panitti E. Cost-Effectiveness Analysis of Vildagliptin vs. Glimepiride as Add-On to Metformin in the Management of Type 2 Diabetes Mellitus in Greece. Value Health. 2015 Nov;18(7):A608. doi: 10.1016/j.jval.2015.09.2101. Epub 2015 Oct 20. PubMed PMID: 26533416.

8: Ambery P, Stylianou A, Atkinson G, Dott C, Baylor Curtis L, Haque N, LaCroix K, Min KW; glimepiride/atorvastatin investigational team. Open-label randomized non-inferiority trial of a fixed-dose combination of glimepiride and atorvastatin for the treatment of people whose Type 2 diabetes is uncontrolled on metformin. Diabet Med. 2015 Oct 20. doi: 10.1111/dme.13003. [Epub ahead of print] PubMed PMID: 26484794.

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