Glyburide | CAS#10238-21-8 | KATP inhibitor

MedKoo Cat#: 317976 | Name: Glyburide

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Description:

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

Glyburide is an antidiabetic sulfonylurea derivative with actions similar to those of chlorpropamide that can potentially be used to decrease cerebral edema. Upon administration, glyburide binds to and blocks the sulfonylurea receptor type 1 (SUR1) subunit of the ATP-sensitive inwardly-rectifying potassium (K(ATP)) channels on the membranes of pancreatic beta cells. This prevents the inward current flow of positively charged potassium (K+) ions into the cell, and induces a calcium ion (Ca2+) influx through voltage-sensitive calcium channels, which triggers exocytosis of insulin-containing granules.

Chemical Structure

Glyburide

CAS#10238-21-8 (free)

Theoretical Analysis

MedKoo Cat#: 317976

Name: Glyburide

CAS#: 10238-21-8 (free)

Chemical Formula: C23H28ClN3O5S

Exact Mass: 493.1438

Molecular Weight: 494.00

Elemental Analysis: C, 55.92; H, 5.71; Cl, 7.18; N, 8.51; O, 16.19; S, 6.49

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 Weeks
25g	USD 550.00	2 Weeks

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Related CAS #

10238-21-8 (free) 20271-40-3 (sodium)

Synonym

Glyburide; Glibenclamide; Glybenclamide; Glynase; Euglucon; NSC-759618; NSC 759618; NSC759618

IUPAC/Chemical Name

5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide

InChi Key

ZNNLBTZKUZBEKO-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

SMILES Code

COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3

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

View handling instruction

Biological target:

Glibenclamide (Glyburide) is an orally active ATP-sensitive K+ channel (KATP) inhibitor. Glibenclamide inhibits P-glycoprotein. Glibenclamide directly binds and blocks the SUR1 subunits of KATP and inhibits the cystic fibrosis transmembrane conductance regulator protein (CFTR).

In vitro activity:

Endothelial cells incubated with a pool of NT (normotensive) plasma induce higher NO levels when compared with the PE (preeclamptic) group (p < 0.05) after 40 min of incubation (Figure 2a). In this group, GB (glibenclamide) treatment increased NO levels (p < 0.05) after 20 min of incubation (Figure 2b) compared with cells without treatment. Reference: Antioxidants (Basel). 2022 Aug 20;11(8):1620. https://pubmed.ncbi.nlm.nih.gov/36009339/

In vivo activity:

In comparison, a significant difference was observed in the time spent in platform quadrants (P = 0.0077) and platform crossings (P = 0.013) between rats with low-dose sevoflurane–inflicted cognitive impairment which received GBC (glibenclamide) and rats which were administered the same low dose but no GBC. These results show that cognitive impairment in rats developed following inhalation of sevoflurane but that memory deficits improved after GBC administration to cognition-deficient rats. Reference: J Vet Res. 2021 Dec 2;65(4):527-538. https://pubmed.ncbi.nlm.nih.gov/35112009/

	Solvent	mg/mL	mM
Solubility
	DMSO	175.0	354.25
	Water	0.1	0.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 494.00 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:

1. Nunes PR, Bueno Pereira TO, Bertozzi Matheus M, Grandini NA, Siqueira JS, Correa CR, Abbade JF, Sandrim VC. Glibenclamide Increases Nitric Oxide Levels and Decreases Oxidative Stress in an In Vitro Model of Preeclampsia. Antioxidants (Basel). 2022 Aug 20;11(8):1620. doi: 10.3390/antiox11081620. PMID: 36009339; PMCID: PMC9404919. 2. Yang J, Yang J, Huang X, Xiu H, Bai S, Li J, Cai Z, Chen Z, Zhang S, Zhang G. Glibenclamide Alleviates LPS-Induced Acute Lung Injury through NLRP3 Inflammasome Signaling Pathway. Mediators Inflamm. 2022 Feb 11;2022:8457010. doi: 10.1155/2022/8457010. PMID: 35185385; PMCID: PMC8856806. 3. Ma Y, Chen X. Glibenclamide Ameliorates the Expression of Neurotrophic Factors in Sevoflurane Anaesthesia-induced Oxidative Stress and Cognitive Impairment in Hippocampal Neurons of Old Rats. J Vet Res. 2021 Dec 2;65(4):527-538. doi: 10.2478/jvetres-2021-0064. PMID: 35112009; PMCID: PMC8775723. 4. Jiang B, Zhang Y, Wang Y, Li Z, Chen Q, Tang J, Zhu G. Glibenclamide Attenuates Neuroinflammation and Promotes Neurological Recovery After Intracerebral Hemorrhage in Aged Rats. Front Aging Neurosci. 2021 Aug 26;13:729652. doi: 10.3389/fnagi.2021.729652. PMID: 34512312; PMCID: PMC8427510.

In vitro protocol:

In vivo protocol:

1. Ma Y, Chen X. Glibenclamide Ameliorates the Expression of Neurotrophic Factors in Sevoflurane Anaesthesia-induced Oxidative Stress and Cognitive Impairment in Hippocampal Neurons of Old Rats. J Vet Res. 2021 Dec 2;65(4):527-538. doi: 10.2478/jvetres-2021-0064. PMID: 35112009; PMCID: PMC8775723. 2. Jiang B, Zhang Y, Wang Y, Li Z, Chen Q, Tang J, Zhu G. Glibenclamide Attenuates Neuroinflammation and Promotes Neurological Recovery After Intracerebral Hemorrhage in Aged Rats. Front Aging Neurosci. 2021 Aug 26;13:729652. doi: 10.3389/fnagi.2021.729652. PMID: 34512312; PMCID: PMC8427510.

1: Bircsak KM, Gupta V, Yuen PY, Gorczyca L, Weinberger BI, Vetrano AM, Aleksunes LM. Genetic and Dietary Regulation of Glyburide Efflux by the Human Placental BCRP Transporter. J Pharmacol Exp Ther. 2016 Feb 5. pii: jpet.115.230185. [Epub ahead of print] PubMed PMID: 26850786. 2: Sheth KN, Elm JJ, Beslow LA, Sze GK, Kimberly WT. Glyburide Advantage in Malignant Edema and Stroke (GAMES-RP) Trial: Rationale and Design. Neurocrit Care. 2016 Feb;24(1):132-9. doi: 10.1007/s12028-015-0189-7. PubMed PMID: 26268138. 3: Harper LM, Glover AV, Biggio JR, Tita A. Predicting failure of glyburide therapy in gestational diabetes. J Perinatol. 2016 Jan 21. doi: 10.1038/jp.2015.216. [Epub ahead of print] PubMed PMID: 26796130. 4: Rezai S, Vielman M, Henderson CE. Glyburide vs Insulin and Adverse Pregnancy Outcomes. JAMA Pediatr. 2015 Oct;169(10):974-5. doi: 10.1001/jamapediatrics.2015.1808. PubMed PMID: 26437012. 5: Tuccori M, Wu JW, Yin H, Majdan A, Azoulay L. The Use of Glyburide Compared With Other Sulfonylureas and the Risk of Cancer in Patients With Type 2 Diabetes. Diabetes Care. 2015 Nov;38(11):2083-9. doi: 10.2337/dc15-1358. Epub 2015 Sep 4. PubMed PMID: 26341130.