Glibenclamide

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Glibenclamide
Glibenclamide.svg
Glibenclamide-4YVP-ball-and-stick.png
Clinical data
Trade names Diabeta, Glynase, Micronase, others [1]
Other namesGlyburide (USAN US)
AHFS/Drugs.com Monograph
MedlinePlus a684058
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 binding Extensive
Metabolism Liver hydroxylation (CYP2C9-mediated)
Elimination half-life 10 hours
Excretion Kidney 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 InfoCard 100.030.505 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H28ClN3O5S
Molar mass 494.00 g·mol−1
3D model (JSmol)
Melting point 169 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) Yes check.svgY
  • Key:ZNNLBTZKUZBEKO-UHFFFAOYSA-N Yes check.svgY
   (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]

Contents

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 2022, it was the 200th most commonly prescribed medication in the United States, with more than 2 million prescriptions. [5] [6]

Medical uses

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]

Adverse effects

Common adverse effects (1 - 10%) include: [8]

Undefined frequency effect: [8]

Rare adverse effects (less than 1%): [8]

Contraindications

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

Pregnancy and breastfeeding

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

Mechanism of action

The medication 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. [8]

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. [13] Moreover, under ischemic conditions SUR1, the regulatory subunit of the KATP- and the NCCa-ATP-channels, is expressed in neurons, astrocytes, oligodendrocytes, endothelial cells [14] and by reactive microglia. [13]

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. [15] [16]

History

It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis). [17]

Society and culture

Names

Glibenclamide is available as a generic medication, is manufactured by many pharmaceutical companies and is sold 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. [18]

Related Research Articles

<span class="mw-page-title-main">Glipizide</span> Chemical compound

Glipizide, sold under the brand name Glucotrol among others, is an anti-diabetic medication of the sulfonylurea class used to treat type 2 diabetes. It is used together with a diabetic diet and exercise. It is not indicated for use by itself in type 1 diabetes. It is taken by mouth. Effects generally begin within half an hour and can last for up to a day.

<span class="mw-page-title-main">Glimepiride</span> Group of stereoisomers

Glimepiride, is an anti-diabetic medication used to treat type 2 diabetes. It is less preferred than metformin. Use is recommended together with diet and exercise. It is taken by mouth. Glimepiride takes up to three hours for maximum effect and lasts for about a day.

<span class="mw-page-title-main">Metformin</span> Medication used to treat diabetes by reducing glucose levels

Metformin is the main first-line medication for the treatment of type 2 diabetes, particularly in people who are overweight. It is also used in the treatment of polycystic ovary syndrome. It is sometimes used as an off-label adjunct to lessen the risk of metabolic syndrome in people who take antipsychotics. Metformin is not associated with weight gain and is taken by mouth.

Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exception of insulin, most GLP receptor agonists, and pramlintide, all are administered orally and are thus also called oral hypoglycemic agents or oral antihyperglycemic agents. There are different classes of anti-diabetic drugs, and their selection depends on the nature of diabetes, age, and situation of the person, as well as other factors.

<span class="mw-page-title-main">Rosiglitazone</span> Chemical compound

Rosiglitazone is an antidiabetic drug in the thiazolidinedione class. It works as an insulin sensitizer, by binding to the PPAR in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug or for use in combination with metformin or with glimepiride. First released in 1999, annual sales peaked at approximately $2.5-billion in 2006; however, following a meta-analysis in 2007 that linked the drug's use to an increased risk of heart attack, sales plummeted to just $9.5-million in 2012. The drug's patent expired in 2012.

<span class="mw-page-title-main">Sulfonylurea</span> Class of organic compounds used in medicine and agriculture

Sulfonylureas or sulphonylureas are a class of organic compounds used in medicine and agriculture. The functional group consists of a sulfonyl group (-S(=O)2) with its sulphur atom bonded to nitrogen atom of a ureylene group (N,N-dehydrourea, a urea derivative). The side chains R1 and R2 distinguish various sulfonylureas.

<span class="mw-page-title-main">Chlorpropamide</span> Chemical compound

Chlorpropamide is an antidiabetic drug, belonging to the sulfonylurea class of organic compounds. It is used to treat diabetes mellitus type 2. It is a long-acting first-generation sulfonylurea.

<span class="mw-page-title-main">Diazoxide</span> Medication used to treat low blood sugar and high blood pressure

Diazoxide, sold under the brand name Proglycem and others, is a medication used to treat low blood sugar due to a number of specific causes. This includes islet cell tumors that cannot be removed and leucine sensitivity. It can also be used in refractory cases of sulfonylurea toxicity. It is generally taken by mouth.

<span class="mw-page-title-main">Acetohexamide</span> Chemical compound

Acetohexamide is a first-generation sulfonylurea medication used to treat diabetes mellitus type 2, particularly in people whose diabetes cannot be controlled by diet alone.

<span class="mw-page-title-main">Exenatide</span> Medication

Exenatide, sold under the brand name Byetta and Bydureon among others, is a medication used to treat diabetes mellitus type 2. It is used together with diet, exercise, and potentially other antidiabetic medication. It is a treatment option after metformin and sulfonylureas. It is given by injection under the skin. A once-weekly injection version is also available.

<span class="mw-page-title-main">Meglitinide</span> Chemical substance

Meglitinides or glinides are a class of drugs used to treat type 2 diabetes.

<span class="mw-page-title-main">Gliclazide</span> Chemical compound

Gliclazide, sold under the brand name Diamicron among others, is a sulfonylurea type of anti-diabetic medication, used to treat type 2 diabetes. It is used when dietary changes, exercise, and weight loss are not enough. It is taken by mouth.

<span class="mw-page-title-main">Sitagliptin</span> Diabetes medication

Sitagliptin, sold under the brand name Januvia among others, is an anti-diabetic medication used to treat type 2 diabetes. In the United Kingdom it is listed as less preferred than metformin or a sulfonylurea. It is taken by mouth. It is also available in the fixed-dose combination medication sitagliptin/metformin.

An ATP-sensitive potassium channel is a type of potassium channel that is gated by intracellular nucleotides, ATP and ADP. ATP-sensitive potassium channels are composed of Kir6.x-type subunits and sulfonylurea receptor (SUR) subunits, along with additional components. KATP channels are found in the plasma membrane; however some may also be found on subcellular membranes. These latter classes of KATP channels can be classified as being either sarcolemmal ("sarcKATP"), mitochondrial ("mitoKATP"), or nuclear ("nucKATP").

<span class="mw-page-title-main">Saxagliptin</span> Chemical compound

Saxagliptin, sold under the brand name Onglyza, is an oral hypoglycemic of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug.

In molecular biology, the sulfonylurea receptors (SUR) are membrane proteins which are the molecular targets of the sulfonylurea class of antidiabetic drugs whose mechanism of action is to promote insulin release from pancreatic beta cells. More specifically, SUR proteins are subunits of the inward-rectifier potassium ion channels Kir6.x. The association of four Kir6.x and four SUR subunits form an ion conducting channel commonly referred to as the KATP channel.

K<sub>ir</sub>6.2 Protein-coding gene in the species Homo sapiens

Kir6.2 is a major subunit of the ATP-sensitive K+ channel, a lipid-gated inward-rectifier potassium ion channel. The gene encoding the channel is called KCNJ11 and mutations in this gene are associated with congenital hyperinsulinism.

<span class="mw-page-title-main">Glicaramide</span> Chemical compound

Glicaramide (SQ-65993) is an orally bioavailable anti-diabetic medication. It has a similar potency as glibenclamide (glyburide) in the class of medication known as sulfonylureas. Its structure is similar since it has a cyclic acyl group which replaces the latter's 2-methoxy-5-chlorobenzyl. Same as glibenclamide, it is classified as a second-generation sulfonylurea. It may have more pronounced extra-pancreatic effects than glibenclamide or tolbutamide.

<span class="mw-page-title-main">Glybuzole</span> Chemical compound

Glybuzole is a hypoglycaemic medicine, mainly used to treat diabetes mellitus type 2. It is an oral antidiabetic drug (OAD), when administered in the right dose it will help bring the blood glycose level down by stimulating the insulin production. Similar medicines are glimepiride, glipizide, glibenclamide, gliclazide, and gliquidone.

Glibenclamide/metformin, also known as glyburide/metformin and sold under the brand name Glucovance, is a fixed-dose combination anti-diabetic medication used to treat type 2 diabetes. It contains glibenclamide, a sulfonylureas, and metformin, a biguanide.

References

  1. 1 2 3 4 5 6 7 8 9 10 "Glyburide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 18 March 2019.
  2. 1 2 "Glynase- glyburide tablet". DailyMed. 7 October 2017. Retrieved 30 April 2022.
  3. 1 2 3 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 2020". ClinCalc. Retrieved 7 October 2022.
  6. ↑ "Glyburide - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  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. 1 2 3 4 "Glyburide". Lexicomp. Wolters Kluwer N.V.
  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. 1 2 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.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ "Glyburide and metformin". Lexicomp. Wolters Kluwer N.V.
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