Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Glibenclamide: Difference between pages

{{Short description|Chemical compound}}

{{Distinguish|gliclazide|glipizide}}

{{Use dmy dates|date=March 2024}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 461120828

| width = 275

| alt =

| image2 = Glibenclamide-4YVP-ball-and-stick.png

| alt2 =

| caption =

| USAN = Glyburide

<!-- Clinical data -->

| pronounce =

| tradename = Diabeta, Glynase, Micronase, others<ref name=AHFS2019/>

| Drugs.com = {{drugs.com|monograph|glyburide}}

| DailyMedID = Glyburide

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = [[Oral administration|By mouth]]

| class =

| ATCvet =

| ATC_prefix = A10

| ATC_suffix = BB01

| ATC_supplemental =

<!-- Legal status -->

| legal_AU = S4

| legal_AU_comment =

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->

| legal_BR_comment =

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_CA_comment =

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK_comment =

| legal_US_comment = <ref name="Glynase FDA label">{{cite web | title=Glynase- glyburide tablet | website=DailyMed | date=7 October 2017 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a7fce80a-2f13-43cc-8e1c-561f7d3ec3d5 | access-date=30 April 2022}}</ref>

| legal_EU = Rx-only

| legal_EU_comment =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_UN_comment =

| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->

| bioavailability =

| metabolism = [[Liver]] [[hydroxylation]] ([[CYP2C9]]-mediated)

| metabolites =

| onset =

| duration_of_action =

| excretion = [[Kidney]] and [[bile duct]]

<!-- Identifiers -->

| CAS_supplemental =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

<!-- Chemical and physical data -->

| IUPAC_name = 5-chloro-''N''-[2-[4-(cyclohexylcarbamoylsulfamoyl)<br />phenyl]ethyl]-2-methoxybenzamide

| C=23 | H=28 | Cl=1 | N=3 | O=5 | S=1

| SMILES = O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCNC(=O)c3cc(Cl)ccc3OC

| density =

| density_notes =

| melting_point = 169

| melting_high = 170

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<!-- Definition and medical uses -->

'''Glibenclamide''', also known as '''glyburide''', is an [[antidiabetic medication]] used to treat [[type 2 diabetes]].<ref name=AHFS2019/> It is recommended that it be taken together with diet and exercise.<ref name=AHFS2019/> It may be used with other [[antidiabetic medication]].<ref name=AHFS2019/> It is not recommended for use by itself in [[type 1 diabetes]].<ref name=AHFS2019/> It is taken [[Oral administration|by mouth]].<ref name=AHFS2019>{{cite web |title=Glyburide Monograph for Professionals |url=https://www.drugs.com/monograph/glyburide.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=18 March 2019 }}</ref>

<!-- Side effects and mechanisms -->

Common side effects include nausea and heartburn.<ref name=AHFS2019/> Serious side effects may include [[angioedema]] and [[low blood sugar]].<ref name=AHFS2019/> It is generally not recommended during [[pregnancy]] but can be used during [[breastfeeding]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=692|edition=76}}</ref> It is in the [[sulfonylurea]]s class of medications and works by increasing the release of [[insulin]] from the [[pancreas]].<ref name=AHFS2019/>

<!-- Society and culture -->

Glibenclamide was discovered in 1969 and approved for medical use in the United States in 1984.<ref>{{cite book |title=Diabetes in Clinical Practice: Questions and Answers from Case Studies |date=2007 |publisher=John Wiley & Sons |isbn=9780470059135 |page=342 |url=https://books.google.com/books?id=fs0M4dPuNtUC&pg=PA342}}</ref><ref name=AHFS2019/> It is available as a [[generic medication]].<ref name=BNF76/> In 2021, it was the 214th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Glyburide - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Glyburide | access-date = 14 January 2024}}</ref>

== Medical uses ==

Glibenclamide is indicated as an adjunct to diet and exercise to improve glycemic control in adults with [[type 2 diabetes]].<ref name="Glynase FDA label" />

It is not as good as either [[metformin]] or [[insulin]] in those who have [[gestational diabetes]].<ref>{{cite journal | vauthors = Balsells M, García-Patterson A, Solà I, Roqué M, Gich I, Corcoy R | title = Glibenclamide, metformin, and insulin for the treatment of gestational diabetes: a systematic review and meta-analysis | journal = BMJ | volume = 350 | pages = h102 | date = January 2015 | pmid = 25609400 | pmc = 4301599 | doi = 10.1136/bmj.h102 }}</ref>

== Side effects ==

Frequently reported side effects include: nausea, heartburn, weight gain, and bloating.<ref>{{cite web |title=Glyburide: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a684058.html |website=MedlinePlus |access-date=29 October 2019 }}</ref> The medication is also a major cause of medication-induced [[hypoglycemia]]. The risk is greater than with other [[sulfonylurea]]s.<ref>{{cite journal | vauthors = Gangji AS, Cukierman T, Gerstein HC, Goldsmith CH, Clase CM | title = A systematic review and meta-analysis of hypoglycemia and cardiovascular events: a comparison of glyburide with other secretagogues and with insulin | journal = Diabetes Care | volume = 30 | issue = 2 | pages = 389–394 | date = February 2007 | pmid = 17259518 | doi = 10.2337/dc06-1789 | title-link = doi | doi-access = free }}</ref>

== Contraindications ==

Glibenclamide may be not recommended in those with [[G6PD deficiency]], as it may cause acute [[hemolysis]].<ref name="pmid8562390">{{cite journal | vauthors = Meloni G, Meloni T | title = Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM | journal = British Journal of Haematology | volume = 92 | issue = 1 | pages = 159–160 | date = January 1996 | pmid = 8562390 | doi = 10.1046/j.1365-2141.1996.275810.x | s2cid = 41227257 }}</ref>

===Pregnancy and breastfeeding===

It is generally not recommended during [[pregnancy]] but can be used during [[breastfeeding]].<ref name=BNF76/>

== Mechanism of action ==

The medication, a [[sulfonylurea]], works by binding to and inhibiting the [[ATP-sensitive potassium channel]]s (K_ATP) inhibitory regulatory subunit [[ABCC8|sulfonylurea receptor 1]] (SUR1)<ref name="pmid17015627">{{cite journal | vauthors = Serrano-Martín X, Payares G, Mendoza-León A | title = Glibenclamide, a blocker of K+(ATP) channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis | journal = Antimicrobial Agents and Chemotherapy | volume = 50 | issue = 12 | pages = 4214–4216 | date = December 2006 | pmid = 17015627 | pmc = 1693980 | doi = 10.1128/AAC.00617-06 }}</ref> in [[pancreas|pancreatic]] [[beta cell]]s. This inhibition causes cell membrane [[depolarization]], opening [[voltage-dependent calcium channel|voltage-dependent calcium Channels.]]<ref>{{cite journal | vauthors = He Y, Chang Y, Peng Y, Zhu J, Liu K, Chen J, Wu Y, Ji Z, Lin Z, Wang S, Gupta S, Zang N, Pan S, Huang K | display-authors = 6 | title = Glibenclamide Directly Prevents Neuroinflammation by Targeting SUR1-TRPM4-Mediated NLRP3 Inflammasome Activation In Microglia | journal = Molecular Neurobiology | volume = 59 | issue = 10 | pages = 6590–6607 | date = October 2022 | pmid = 35972671 | doi = 10.1007/s12035-022-02998-x | s2cid = 242029244 }}</ref>

This results in an increase in intracellular [[calcium]] in the pancreatic [[beta cell]] and subsequent stimulation of [[insulin]] release.<ref name="Lexicomp">{{Cite web | publisher = Wolters Kluwer N.V. |title=Glyburide |url= https://www.wolterskluwer.com/en/solutions/lexicomp |website=Lexicomp}}</ref>

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.<ref name="pmid22387180">{{cite journal | vauthors = Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, Mahy N, Rodríguez MJ | display-authors = 6 | title = ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats | journal = Experimental Neurology | volume = 235 | issue = 1 | pages = 282–296 | date = May 2012 | pmid = 22387180 | doi = 10.1016/j.expneurol.2012.02.010 | hdl-access = free | s2cid = 4828181 | hdl = 2445/34278 }}</ref> Moreover, under ischemic conditions SUR1, the regulatory subunit of the K_ATP- and the NC_Ca-ATP-channels, is expressed in neurons, [[astrocyte]]s, [[oligodendrocyte]]s, [[endothelial cell]]s<ref name="pmid22714048">{{cite journal | vauthors = Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V | title = Sulfonylurea receptor 1 in central nervous system injury: a focused review | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 32 | issue = 9 | pages = 1699–1717 | date = September 2012 | pmid = 22714048 | pmc = 3434627 | doi = 10.1038/jcbfm.2012.91 }}</ref> and by reactive [[microglia]].<ref name="pmid22387180"/>

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.<ref>{{cite journal | vauthors = Chen S, Ogawa A, Ohneda M, Unger RH, Foster DW, McGarry JD | title = More direct evidence for a malonyl-CoA-carnitine palmitoyltransferase I interaction as a key event in pancreatic beta-cell signaling | journal = Diabetes | volume = 43 | issue = 7 | pages = 878–883 | date = July 1994 | pmid = 8013751 | doi = 10.2337/diab.43.7.878 | s2cid = 25251669 }}</ref><ref>{{cite journal | vauthors = Lehtihet M, Welsh N, Berggren PO, Cook GA, Sjoholm A | title = Glibenclamide inhibits islet carnitine palmitoyltransferase 1 activity, leading to PKC-dependent insulin exocytosis | journal = American Journal of Physiology. Endocrinology and Metabolism | volume = 285 | issue = 2 | pages = E438–E446 | date = August 2003 | pmid = 12684219 | doi = 10.1152/ajpendo.00057.2003 | s2cid = 175394 }}</ref>

==History==

It was developed in 1966 in a cooperative study between [[Boehringer Mannheim]] (now part of [[Hoffmann–La Roche|Roche]]) and [[Hoechst AG|Hoechst]] (now part of [[Sanofi-Aventis]]).<ref name="pmid4999930">{{cite journal | vauthors = Marble A | title = Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents? | journal = Drugs | volume = 1 | issue = 2 | pages = 109–115 | year = 1971 | pmid = 4999930 | doi = 10.2165/00003495-197101020-00001 | s2cid = 13181386 }}</ref>

== Society and culture ==

=== Brand names ===

Glibenclamide is available as a [[Generic drug|generic medication]], is manufactured by many pharmaceutical companies and is sold under many brand names including Gliben-J, Daonil,<ref>{{Cite web |title=Daonil |url=https://www.news-medical.net/drugs/Daonil.aspx |access-date=26 June 2023 |website=News-Medical.net |language=en}}</ref> Diabeta,<ref>{{Cite web |title=DiaBeta (Glyburide Tablets): Uses, Dosage, Side Effects, Interactions, Warning |url=https://www.rxlist.com/diabeta-drug.htm |access-date=26 June 2023 |website=RxList |language=en}}</ref> 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.<ref name="Lexicomp2">{{Cite web | publisher = Wolters Kluwer N.V. |title=Glyburide and metformin |url= https://www.wolterskluwer.com/en/solutions/lexicomp |website=Lexicomp}}</ref>

== References ==

{{Reflist}}

{{Oral hypoglycemics}}

{{Ion channel modulators}}

{{Portal bar | Medicine}}

[[Category:Disulfiram-like drugs]]

[[Category:Potassium channel blockers]]

[[Category:Benzamides]]

[[Category:Chloroarenes]]

[[Category:Phenol ethers]]

[[Category:1-(Benzenesulfonyl)-3-cyclohexylureas]]

[[Category:Sanofi]]

[[Category:Wikipedia medicine articles ready to translate]]