Glibenclamide

Glibenclamide
Clinical data
Trade names	Diabeta, Flycron, others[1]
Other names	Glyburide (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a684058
License data	US DailyMed: Glyburide; US FDA: Glyburide;
Pregnancy; category	AU: C ; US: B (No risk in non-human studies) ;
Routes of; administration	By mouth
ATC code	A10BB01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Protein binding	Extensive
Metabolism	Liver hydroxylation (CYP2C9-mediated)
Elimination half-life	10 hours
Excretion	Kidney and biliary
Identifiers
	IUPAC name 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl); phenyl]ethyl]-2-methoxybenzamide;
CAS Number	10238-21-8 ;
PubChem CID	3488;
IUPHAR/BPS	2414;
DrugBank	DB01016 ;
ChemSpider	3368 ;
UNII	SX6K58TVWC;
KEGG	D00336 ;
ChEBI	CHEBI:5441 ;
ChEMBL	ChEMBL472 ;
CompTox Dashboard (EPA)	DTXSID0037237 ;
ECHA InfoCard	100.030.505
Chemical and physical data
Formula	C23H28ClN3O5S
Molar mass	494.00 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	169 to 170 °C (336 to 338 °F)
	SMILES O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCNC(=O)c3cc(Cl)ccc3OC;
	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) ; Key:ZNNLBTZKUZBEKO-UHFFFAOYSA-N ;
	(verify)

Glibenclamide, also known as glyburide, is a medication used to treat diabetes mellitus type 2.[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 diabetes mellitus type 1.[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.[2] 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.[3][1] It is available as a generic medication.[2] In 2017, it was the 174th most commonly prescribed medication in the United States, with more than three million prescriptions.[4][5]

Medical uses

It is used in the treatment of type 2 diabetes.

It is not as good as either metformin or insulin in those who have gestational diabetes.[6]

Side effects

Frequently reported side effects include: nausea, heartburn, weight gain, and bloating.[7] The medication is also a major cause of medication-induced hypoglycemia. The risk is greater than with other sulfonylureas.[8] Cholestatic jaundice is noted.

Glibenclamide may be not recommended in those with G6PD deficiency, as it may cause acute hemolysis.[9]

Pregnancy and breastfeeding

It is generally not recommended during pregnancy but can be used during breastfeeding.[2]

Mechanism of action

The medication works by binding to and inhibiting the ATP-sensitive potassium channels (K_ATP) inhibitory regulatory subunit sulfonylurea receptor 1 (SUR1)[10] in pancreatic beta cells. This inhibition causes cell membrane depolarization, opening voltage-dependent calcium channels. This results in an increase in intracellular calcium in the pancreatic beta cell and subsequent stimulation of insulin release.

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.[11] Moreover, under ischemic conditions SUR1, the regulatory subunit of the K_ATP- and the NC_Ca-ATP-channels, is expressed in neurons, astrocytes, oligodendrocytes, endothelial cells[12] and by reactive microglia.[11]

History

It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis).[13]

Trade names

Glibenclamide is available as a generic, is manufactured by many pharmaceutical companies and is sold in doses of 1.25, 2.5 and 5 mg under many brand names including Gliben-J, Daonil, Diabeta, 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.

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References

"Glyburide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 18 March 2019.
British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 692. ISBN 9780857113382.
Diabetes in Clinical Practice: Questions and Answers from Case Studies. John Wiley & Sons. 2007. p. 342. ISBN 9780470059135.
"The Top 300 of 2020". ClinCalc. Retrieved 11 April 2020.
"Glyburide - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.
Balsells, M; García-Patterson, A; Solà, I; Roqué, M; Gich, I; Corcoy, R (21 January 2015). "Glibenclamide, metformin, and insulin for the treatment of gestational diabetes: a systematic review and meta-analysis". BMJ (Clinical Research Ed.). 350: h102. doi:10.1136/bmj.h102. PMC 4301599. PMID 25609400.
"Glyburide: MedlinePlus Drug Information". medlineplus.gov. Retrieved 29 October 2019.
Gangji, A. S.; Cukierman, T.; Gerstein, H. C.; Goldsmith, C. H.; Clase, C. M. (1 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.
Meloni G, Meloni T (January 1996). "Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM". Br. J. Haematol. 92 (1): 159–60. doi:10.1046/j.1365-2141.1996.275810.x. PMID 8562390.
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". Antimicrob. Agents Chemother. 50 (12): 4214–6. doi:10.1128/AAC.00617-06. PMC 1693980. PMID 17015627.
Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, Mahy N, Rodríguez MJ (May 2012). "ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats" (PDF). Exp. Neurol. 235 (1): 282–96. doi:10.1016/j.expneurol.2012.02.010. hdl:2445/34278. PMID 22387180.
Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V (September 2012). "Sulfonylurea receptor 1 in central nervous system injury: a focused review". J. Cereb. Blood Flow Metab. 32 (9): 1699–717. doi:10.1038/jcbfm.2012.91. PMC 3434627. PMID 22714048.
Marble A (1971). "Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents?". Drugs. 1 (2): 109–15. doi:10.2165/00003495-197101020-00001. PMID 4999930.

External links

"Glyburide". Drug Information Portal. U.S. National Library of Medicine.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[AHFS2019-1] "Glyburide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 18 March 2019.

[BNF76-2] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 692. ISBN 9780857113382.

[3] Diabetes in Clinical Practice: Questions and Answers from Case Studies. John Wiley & Sons. 2007. p. 342. ISBN 9780470059135.

[4] "The Top 300 of 2020". ClinCalc. Retrieved 11 April 2020.

[5] "Glyburide - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.

[6] Balsells, M; García-Patterson, A; Solà, I; Roqué, M; Gich, I; Corcoy, R (21 January 2015). "Glibenclamide, metformin, and insulin for the treatment of gestational diabetes: a systematic review and meta-analysis". BMJ (Clinical Research Ed.). 350: h102. doi:10.1136/bmj.h102. PMC 4301599. PMID 25609400.

[7] "Glyburide: MedlinePlus Drug Information". medlineplus.gov. Retrieved 29 October 2019.

[8] Gangji, A. S.; Cukierman, T.; Gerstein, H. C.; Goldsmith, C. H.; Clase, C. M. (1 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.

[pmid8562390-9] Meloni G, Meloni T (January 1996). "Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM". Br. J. Haematol. 92 (1): 159–60. doi:10.1046/j.1365-2141.1996.275810.x. PMID 8562390.

[pmid17015627-10] 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". Antimicrob. Agents Chemother. 50 (12): 4214–6. doi:10.1128/AAC.00617-06. PMC 1693980. PMID 17015627.

[pmid22387180-11] Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, Mahy N, Rodríguez MJ (May 2012). "ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats" (PDF). Exp. Neurol. 235 (1): 282–96. doi:10.1016/j.expneurol.2012.02.010. hdl:2445/34278. PMID 22387180.

[pmid22714048-12] Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V (September 2012). "Sulfonylurea receptor 1 in central nervous system injury: a focused review". J. Cereb. Blood Flow Metab. 32 (9): 1699–717. doi:10.1038/jcbfm.2012.91. PMC 3434627. PMID 22714048.

[pmid4999930-13] Marble A (1971). "Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents?". Drugs. 1 (2): 109–15. doi:10.2165/00003495-197101020-00001. PMID 4999930.