Difference between revisions of "Glibenclamide"
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| − | It is sold in doses of 1.25 mg, 2.5 mg and 5 mg, under the trade names '''Diabeta''', '''Glynase''' and '''Micronase''' in the [[United States]] and '''Daonil''', '''Semi-Daonil''' and '''Euglucon''' in the [[United Kingdom]]. | + | It is sold in doses of 1.25 mg, 2.5 mg and 5 mg, under the trade names '''Diabeta''', '''Glynase''' and '''Micronase''' in the [[United States]] and '''Daonil''', '''Semi-Daonil''' and '''Euglucon''' in the [[United Kingdom]] and '''Delmide''' in [[India]]. |
It is also sold in combination with [[metformin]] under the trade names '''Glucovance''' and '''Glibomet'''. | It is also sold in combination with [[metformin]] under the trade names '''Glucovance''' and '''Glibomet'''. | ||
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[[de:Glibenclamid]] | [[de:Glibenclamid]] | ||
Latest revision as of 20:12, 31 August 2010
| File:Glibenclamide.svg | |
| File:Glibenclamide 3D.png | |
| Systematic (IUPAC) name | |
|---|---|
|
5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide | |
| Clinical data | |
| [[Regulation of therapeutic goods |Template:Engvar data]] | |
| Pregnancy category | |
| Routes of administration | Oral |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | Extensive |
| Metabolism | Hepatic hydroxylation (CYP2C9-mediated) |
| Biological half-life | 10 hours |
| Excretion | Renal and biliary |
| Identifiers | |
| CAS Number | 10238-21-8 |
| ATC code | A10BB01 (WHO) |
| PubChem | CID 3488 |
| IUPHAR/BPS | 2414 |
| DrugBank | APRD00233 |
| ChemSpider | 3368 |
| Chemical data | |
| Formula | C23H28ClN3O5S |
| Molar mass | 494.004 g/mol[[Script error: No such module "String".]] |
| (verify) | |
Glibenclamide (INN), also known as glyburide (USAN), is an anti-diabetic drug in a class of medications known as sulfonylureas, closely related to sulfa drugs. It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of sanofi-aventis).[1]
It is sold in doses of 1.25 mg, 2.5 mg and 5 mg, under the trade names Diabeta, Glynase and Micronase in the United States and Daonil, Semi-Daonil and Euglucon in the United Kingdom and Delmide in India.
It is also sold in combination with metformin under the trade names Glucovance and Glibomet.
Uses
It is used in the treatment of type II diabetes. As of 2007[update], it is one of only two oral anti-diabetics in the World Health Organization Model List of Essential Medicines (the other being metformin).[2] As of 2003, in the United States, it was the most popular sulfonylurea.[3]
Additionally, recent research shows that glyburide improves outcome in animal stroke models by preventing brain swelling. A retrospective study showed that in type 2 diabetic patients already taking glyburide there was improved NIH stroke scale scores on discharge compared to diabetic patients not taking glyburide.
Mechanism of action
The drug works by inhibiting ATP-sensitive potassium channels[4] in pancreatic beta cells. This inhibition causes cell membrane depolarization, which causes voltage-dependent calcium channels to open, which causes an increase in intracellular calcium in the beta cell, which stimulates insulin release.
Side effects and contraindications
This drug is a major cause of drug induced hypoglycemia. Cholestatic jaundice is noted.
Recently published data suggests that glibenclamide is associated with significantly higher annual mortality when combined with metformin than other insulin-secreting medications, after correcting for other potentially confounding patient characteristics. The safety of this combination has been questioned.[5]
Synthesis
The N-acetyl derivative of β-phenethylamine is reacted with chlorosulfonic acid to form the para sulfonyl chloride derivative. This is then subjected to ammonolysis, followed by base-catalyzed removal of the acetamide. This is then acylated with 2-methoxy-5-chlorobenzoic acid chloride to give the amide intermediate. This is then reacted with cyclohexyl isocyanate to yield the sulfonylurea glibenclamide.
Hsi, R. S. P. (1973). "Synthesis of carbon-14 and tritium labeled glyburide". Journal of Labelled Compounds. 9: 91. doi:10.1002/jlcr.2590090112.
References
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es:Glibenclamida fa:گلیبن کلامید it:Glibenclamide pl:Glibenklamid
zh:格列苯脲- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ (March 2007) WHO Model List of Essential MedicinesPDF (612 KiB), 15th edition, World Health Organization, p. 21. Retrieved on 2007-11-19.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E (2006). "Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin". Diabetes Metab Res Rev. 22 (6): 477–82. doi:10.1002/dmrr.642. PMID 16634115.
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