Glyburide (Glibenclamide)

  • CAT Number: A000747
  • CAS Number: 10238-21-8
  • Molecular Formula: C23H28ClN3O5S
  • Molecular Weight: 494.003
  • Purity: ≥95%
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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.

Catalog Number A000747
CAS Number 10238-21-8
Molecular Formula

C23H28ClN3O5S

Purity 95%
Target Saccharometabolism
Solubility Soluble in DMSO
Storage 3 years -20C powder
IUPAC Name 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
InChI 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)
InChIKey ZNNLBTZKUZBEKO-UHFFFAOYSA-N
SMILES COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
Reference

</br>1: Bircsak KM, Gupta V, Yuen PY, Gorczyca L, Weinberger BI, Vetrano AM, Aleksunes</br> LM. Genetic and Dietary Regulation of Glyburide Efflux by the Human Placental</br> BCRP Transporter. J Pharmacol Exp Ther. 2016 Feb 5. pii: jpet.115.230185. [Epub</br> ahead of print] PubMed PMID: 26850786.</br>2: Sheth KN, Elm JJ, Beslow LA, Sze GK, Kimberly WT. Glyburide Advantage in</br> Malignant Edema and Stroke (GAMES-RP) Trial: Rationale and Design. Neurocrit</br> Care. 2016 Feb;24(1):132-9. doi: 10.1007/s12028-015-0189-7. PubMed PMID:</br> 26268138.</br>3: Harper LM, Glover AV, Biggio JR, Tita A. Predicting failure of glyburide</br> therapy in gestational diabetes. J Perinatol. 2016 Jan 21. doi:</br> 10.1038/jp.2015.216. [Epub ahead of print] PubMed PMID: 26796130.</br>4: Samala S, Veeresham C. Pharmacokinetic and Pharmacodynamic Interaction of</br> Boswellic Acids and Andrographolide with Glyburide in Diabetic Rats: Including</br> Its PK/PD Modeling. Phytother Res. 2016 Jan 13. doi: 10.1002/ptr.5556. [Epub</br> ahead of print] PubMed PMID: 26762235.</br>5: Sheth KN, Simard JM, Elm J, Kronenberg G, Kunte H, Kimberly WT. Human Data</br> Supporting Glyburide in Ischemic Stroke. Acta Neurochir Suppl. 2016;121:13-8.</br> doi: 10.1007/978-3-319-18497-5_3. PubMed PMID: 26463916.</br>6: Glover AV, Tita A, Biggio JR, Harper LM. Examining the Starting Dose of</br> Glyburide in Gestational Diabetes. Am J Perinatol. 2016 Jan;33(2):214-20. doi:</br> 10.1055/s-0035-1564063. Epub 2015 Sep 14. PubMed PMID: 26368915.</br>7: Rezai S, Vielman M, Henderson CE. Glyburide vs Insulin and Adverse Pregnancy</br> Outcomes. JAMA Pediatr. 2015 Oct;169(10):974-5. doi:</br> 10.1001/jamapediatrics.2015.1808. PubMed PMID: 26437012.</br>8: Clemens KK, McArthur E, Dixon SN, Fleet JL, Hramiak I, Garg AX. The</br> hypoglycemic risk of glyburide (glibenclamide) compared with modified-release</br> gliclazide. Can J Diabetes. 2015 Nov;39 Suppl 4:32-40. doi:</br> 10.1016/j.jcjd.2015.09.087. PubMed PMID: 26541489.</br>9: Tuccori M, Wu JW, Yin H, Majdan A, Azoulay L. The Use of Glyburide Compared</br> With Other Sulfonylureas and the Risk of Cancer in Patients With Type 2 Diabetes.</br> Diabetes Care. 2015 Nov;38(11):2083-9. doi: 10.2337/dc15-1358. Epub 2015 Sep 4.</br> PubMed PMID: 26341130.</br>10: Castillo WC, Funk MJ. Glyburide vs Insulin and Adverse Pregnancy</br> Outcomes–Reply. JAMA Pediatr. 2015 Oct;169(10):975. doi:</br> 10.1001/jamapediatrics.2015.1811. PubMed PMID: 26437013.</br>11: Feghali MN, Scifres CM, Caritis SN. Glyburide vs Insulin and Adverse</br> Pregnancy Outcomes. JAMA Pediatr. 2015 Oct;169(10):974. doi:</br> 10.1001/jamapediatrics.2015.1805. PubMed PMID: 26437011.</br>12: Casey BM, Duryea EL, Abbassi-Ghanavati M, Tudela CM, Shivvers SA, McIntire</br> DD, Leveno KJ. Glyburide in Women With Mild Gestational Diabetes: A Randomized</br> Controlled Trial. Obstet Gynecol. 2015 Aug;126(2):303-9. doi:</br> 10.1097/AOG.0000000000000967. PubMed PMID: 26241419.</br>13: Clemens KK, McArthur E, Dixon SN, Fleet JL, Hramiak I, Garg AX. The</br> Hypoglycemic Risk of Glyburide (Glibenclamide) Compared with Modified-Release</br> Gliclazide. Can J Diabetes. 2015 Aug;39(4):308-16. doi:</br> 10.1016/j.jcjd.2015.01.001. Epub 2015 Mar 31. PubMed PMID: 25840942.</br>14: Joy NG, Tate DB, Davis SN. Counterregulatory responses to hypoglycemia differ</br> between glimepiride and glyburide in non diabetic individuals. Metabolism. 2015</br> Jun;64(6):729-37. doi: 10.1016/j.metabol.2015.02.006. Epub 2015 Feb 26. PubMed</br> PMID: 25765720; PubMed Central PMCID: PMC4408247.</br>15: Glyburide, Gliclazide or Glimepiride for Elderly Patients with Type 2</br> Diabetes: A Review of the Clinical Effectiveness and Safety – An Update</br> [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health;</br> 2015 Aug 18. Available from http://www.ncbi.nlm.nih.gov/books/NBK315876/</br> PubMed PMID: 26355189.</br>16: Amin M, Suksomboon N, Poolsup N, Malik O. Comparison of glyburide with</br> metformin in treating gestational diabetes mellitus: a systematic review and</br> meta-analysis. Clin Drug Investig. 2015 Jun;35(6):343-51. doi:</br> 10.1007/s40261-015-0289-3. PubMed PMID: 25985837.</br>17: Jiang S, Zhao W, Chen Y, Zhong Z, Zhang M, Li F, Xu P, Zhao K, Li Y, Liu L,</br> Liu X. Paroxetine decreased plasma exposure of glyburide partly via inhibiting</br> intestinal absorption in rats. Drug Metab Pharmacokinet. 2015 Jun;30(3):240-6.</br> doi: 10.1016/j.dmpk.2015.02.004. Epub 2015 Mar 11. PubMed PMID: 25890690.</br>18: Camelo Castillo W, Boggess K, Stürmer T, Brookhart MA, Benjamin DK Jr,</br> Jonsson Funk M. Association of Adverse Pregnancy Outcomes With Glyburide vs</br> Insulin in Women With Gestational Diabetes. JAMA Pediatr. 2015 May;169(5):452-8. </br> doi: 10.1001/jamapediatrics.2015.74. PubMed PMID: 25822253.</br>19: Holt RI. Glyburide for gestational diabetes: time for a pause for thought.</br> JAMA Pediatr. 2015 May;169(5):427-8. doi: 10.1001/jamapediatrics.2015.144. PubMed</br> PMID: 25821923.</br>20: Zhang X, Wang X, Vernikovskaya DI, Fokina VM, Nanovskaya TN, Hankins GD,</br> Ahmed MS. Quantitative determination of metformin, glyburide and its metabolites </br> in plasma and urine of pregnant patients by LC-MS/MS. Biomed Chromatogr. 2015</br> Apr;29(4):560-9. doi: 10.1002/bmc.3314. Epub 2014 Aug 27. PubMed PMID: 25164921; </br> PubMed Central PMCID: PMC4344438.</br></br>

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