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Glibenclamide

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(Redirected from C23H28ClN3O5S)
Not to be confused with gliclazide or glipizide.

Glibenclamide
Clinical data
Trade namesDiabeta, Glynase, Micronase, others[1]
Other namesGlyburide (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa684058
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only[2]
  • EU: Rx-only
Pharmacokinetic data
Protein bindingExtensive
MetabolismLiver hydroxylation (CYP2C9-mediated)
Elimination half-life10 hours
ExcretionKidney and bile duct
Identifiers
  • 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)
    phenyl]ethyl]-2-methoxybenzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.505 Edit this at Wikidata
Chemical and physical data
FormulaC23H28ClN3O5S
Molar mass494.00 g·mol−1
3D model (JSmol)
Melting point169 to 170 °C (336 to 338 °F)
  • O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCNC(=O)c3cc(Cl)ccc3OC
  • 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) checkY
  • Key:ZNNLBTZKUZBEKO-UHFFFAOYSA-N checkY
  (verify)

Glibenclamide, also known as glyburide, is an antidiabetic medication used to treat type 2 diabetes.[1] It is recommended that it be taken together with diet and exercise.[1] It may be used with other antidiabetic medication.[1] It is not recommended for use by itself in type 1 diabetes.[1] It is taken by mouth.[1]

Common side effects include nausea and heartburn.[1] Serious side effects may include angioedema and low blood sugar.[1] It is generally not recommended during pregnancy but can be used during breastfeeding.[3] It is in the sulfonylureas class of medications and works by increasing the release of insulin from the pancreas.[1]

Glibenclamide was discovered in 1969 and approved for medical use in the United States in 1984.[4][1] It is available as a generic medication.[3] In 2021, it was the 214th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[5][6]

Medical uses

[edit]

Glibenclamide is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes.[2]

It is not as good as either metformin or insulin in those who have gestational diabetes.[7]

Side effects

[edit]

Frequently reported side effects include: nausea, heartburn, weight gain, and bloating.[8] The medication is also a major cause of medication-induced hypoglycemia. The risk is greater than with other sulfonylureas.[9]

Contraindications

[edit]

Glibenclamide may be not recommended in those with G6PD deficiency, as it may cause acute hemolysis.[10]

Pregnancy and breastfeeding

[edit]

It is generally not recommended during pregnancy but can be used during breastfeeding.[3]

Mechanism of action

[edit]

The medication, a sulfonylurea, works by binding to and inhibiting the ATP-sensitive potassium channels (KATP) inhibitory regulatory subunit sulfonylurea receptor 1 (SUR1)[11] in pancreatic beta cells. This inhibition causes cell membrane depolarization, opening voltage-dependent calcium Channels.[12]

This results in an increase in intracellular calcium in the pancreatic beta cell and subsequent stimulation of insulin release.[13]

After a cerebral ischemic insult, the blood–brain barrier is broken and glibenclamide can reach the central nervous system. Glibenclamide has been shown to bind more efficiently to the ischemic hemisphere.[14] Moreover, under ischemic conditions SUR1, the regulatory subunit of the KATP- and the NCCa-ATP-channels, is expressed in neurons, astrocytes, oligodendrocytes, endothelial cells[15] and by reactive microglia.[14]

As per the research papers, this sulphonylurea drugs also has extra hepatic effects. It works by inhibiting the enzyme Carnityl Acyl Transferase I (CAT-I) indirectly which is present in the mitochondria. This prevents the transport of long chain fatty acids into the mitochondria for beta-oxidation. This prevents hyperglycemia for which it is prescribed.[16][17]

History

[edit]

It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis).[18]

Society and culture

[edit]

Brand names

[edit]

Glibenclamide is available as a generic medication, is manufactured by many pharmaceutical companies and is sold under many brand names including Gliben-J, Daonil,[19] Diabeta,[20] Euglucon, Gilemal, Glidanil, Glybovin, Glynase, Maninil, Micronase and Semi-Daonil. It is also available in a fixed-dose combination drug with metformin that is sold under various trade names, e.g. Bagomet Plus, Benimet, Glibomet, Gluconorm, Glucored, Glucovance, Metglib and many others.[21]

References

[edit]
  1. ^ a b c d e f g h i j "Glyburide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 31 March 2019. Retrieved 18 March 2019.
  2. ^ a b "Glynase- glyburide tablet". DailyMed. 7 October 2017. Archived from the original on 6 October 2022. Retrieved 30 April 2022.
  3. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 692. ISBN 9780857113382.
  4. ^ Diabetes in Clinical Practice: Questions and Answers from Case Studies. John Wiley & Sons. 2007. p. 342. ISBN 9780470059135.
  5. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  6. ^ "Glyburide - Drug Usage Statistics". ClinCalc. Archived from the original on 12 April 2020. Retrieved 14 January 2024.
  7. ^ Balsells M, García-Patterson A, Solà I, Roqué M, Gich I, Corcoy R (January 2015). "Glibenclamide, metformin, and insulin for the treatment of gestational diabetes: a systematic review and meta-analysis". BMJ. 350: h102. doi:10.1136/bmj.h102. PMC 4301599. PMID 25609400.
  8. ^ "Glyburide: MedlinePlus Drug Information". MedlinePlus. Archived from the original on 14 April 2019. Retrieved 29 October 2019.
  9. ^ Gangji AS, Cukierman T, Gerstein HC, Goldsmith CH, Clase CM (February 2007). "A systematic review and meta-analysis of hypoglycemia and cardiovascular events: a comparison of glyburide with other secretagogues and with insulin". Diabetes Care. 30 (2): 389–394. doi:10.2337/dc06-1789. PMID 17259518.
  10. ^ Meloni G, Meloni T (January 1996). "Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM". British Journal of Haematology. 92 (1): 159–160. doi:10.1046/j.1365-2141.1996.275810.x. PMID 8562390. S2CID 41227257.
  11. ^ Serrano-Martín X, Payares G, Mendoza-León A (December 2006). "Glibenclamide, a blocker of K+(ATP) channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis". Antimicrobial Agents and Chemotherapy. 50 (12): 4214–4216. doi:10.1128/AAC.00617-06. PMC 1693980. PMID 17015627.
  12. ^ He Y, Chang Y, Peng Y, Zhu J, Liu K, Chen J, et al. (October 2022). "Glibenclamide Directly Prevents Neuroinflammation by Targeting SUR1-TRPM4-Mediated NLRP3 Inflammasome Activation In Microglia". Molecular Neurobiology. 59 (10): 6590–6607. doi:10.1007/s12035-022-02998-x. PMID 35972671. S2CID 242029244.
  13. ^ "Glyburide". Lexicomp. Wolters Kluwer N.V. Archived from the original on 2 June 2023. Retrieved 3 June 2023.
  14. ^ a b Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, et al. (May 2012). "ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats". Experimental Neurology. 235 (1): 282–296. doi:10.1016/j.expneurol.2012.02.010. hdl:2445/34278. PMID 22387180. S2CID 4828181.
  15. ^ Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V (September 2012). "Sulfonylurea receptor 1 in central nervous system injury: a focused review". Journal of Cerebral Blood Flow and Metabolism. 32 (9): 1699–1717. doi:10.1038/jcbfm.2012.91. PMC 3434627. PMID 22714048.
  16. ^ Chen S, Ogawa A, Ohneda M, Unger RH, Foster DW, McGarry JD (July 1994). "More direct evidence for a malonyl-CoA-carnitine palmitoyltransferase I interaction as a key event in pancreatic beta-cell signaling". Diabetes. 43 (7): 878–883. doi:10.2337/diab.43.7.878. PMID 8013751. S2CID 25251669.
  17. ^ Lehtihet M, Welsh N, Berggren PO, Cook GA, Sjoholm A (August 2003). "Glibenclamide inhibits islet carnitine palmitoyltransferase 1 activity, leading to PKC-dependent insulin exocytosis". American Journal of Physiology. Endocrinology and Metabolism. 285 (2): E438–E446. doi:10.1152/ajpendo.00057.2003. PMID 12684219. S2CID 175394.
  18. ^ Marble A (1971). "Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents?". Drugs. 1 (2): 109–115. doi:10.2165/00003495-197101020-00001. PMID 4999930. S2CID 13181386.
  19. ^ "Daonil". News-Medical.net. Archived from the original on 26 June 2023. Retrieved 26 June 2023.
  20. ^ "DiaBeta (Glyburide Tablets): Uses, Dosage, Side Effects, Interactions, Warning". RxList. Archived from the original on 26 June 2023. Retrieved 26 June 2023.
  21. ^ "Glyburide and metformin". Lexicomp. Wolters Kluwer N.V. Archived from the original on 2 June 2023. Retrieved 3 June 2023.
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