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| '''Biguanide''' is the organic compound with the formula HN(C(NH)NH<sub>2</sub>)<sub>2</sub>. It is a colourless solid that dissolves in water to give highly basic solution. These solutions slowly hydrolyse to ammonia and urea.<ref name=Ullmann>Thomas Güthner, Bernd Mertschenk and Bernd Schulz "Guanidine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a12_545.pub2}}</ref> | |||
| ]]] | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ==Biguanidine drugs== | |||
| The disinfectant ] (PAPB) features biguanide functional groups. | |||
| Biguanidine also refers to a class of drugs based upon the biguanidine molecule.<ref>Rang et al., ''Pharmacology'', 5th Edition, 2003, p 388 | |||
| ⚫ | </ref> Biguanides can function as oral antihyperglycemic ]s used for ] or ] treatment. They are also used as ]s.The disinfectant ] (PAPB) features biguanide functional groups. | ||
| ==Examples== | |||
| Examples of biguanides: | Examples of biguanides: | ||
| * ] - widely used in treatment of ] | * ] - widely used in treatment of ] | ||
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| * ] - an ]. | * ] - an ]. | ||
| <gallery caption="bioactive biguanidines" widths="180px" heights="120px" perrow="3"> | |||
| ⚫ | ==History== | ||
| File:Metformin.svg|], an "unsym"-dimethylbiguanidine | |||
| ⚫ | File:Buformin.svg|]. A ] derivative of biguanidine. | ||
| ⚫ | File:Phenformin.svg|]. A phenethylated biguanidine. | ||
| </gallery> | |||
| ⚫ | ===History=== | ||
| '']'' (French lilac) was used for diabetes treatment in traditional medicine for centuries. In the 1920s, ] compounds were discovered in ''Galega'' extracts. Animal studies showed that these compounds lowered blood glucose levels. Some less toxic derivatives, ] A and synthalin B, were used for diabetes treatment, but after the discovery of ] they were forgotten for the next several decades. Biguanides were reintroduced into Type 2 ] treatment in the late 1950s. Initially ] was widely used, but its potential for sometimes fatal ] resulted in its withdrawal from pharmacotherapy in most pharmacopeias (in the U.S. in 1977). Metformin has a much better safety profile, and it is the principal biguanide drug used in pharmacotherapy worldwide. | '']'' (French lilac) was used for diabetes treatment in traditional medicine for centuries. In the 1920s, ] compounds were discovered in ''Galega'' extracts. Animal studies showed that these compounds lowered blood glucose levels. Some less toxic derivatives, ] A and synthalin B, were used for diabetes treatment, but after the discovery of ] they were forgotten for the next several decades. Biguanides were reintroduced into Type 2 ] treatment in the late 1950s. Initially ] was widely used, but its potential for sometimes fatal ] resulted in its withdrawal from pharmacotherapy in most pharmacopeias (in the U.S. in 1977). Metformin has a much better safety profile, and it is the principal biguanide drug used in pharmacotherapy worldwide. | ||
| ===Mechanistic aspects=== | |||
| ==Pharmacotherapy== | |||
| Biguanides do not affect the output of insulin, unlike other ]s such as ]s and ]s. Therefore, not only are they effective in Type 2 diabetics but they can also be effective in Type 1 patients in concert with insulin therapy. | Biguanides do not affect the output of insulin, unlike other ]s such as ]s and ]s. Therefore, not only are they effective in Type 2 diabetics but they can also be effective in Type 1 patients in concert with insulin therapy. | ||
| ==Mechanism of action== | |||
| The ] of biguanides is not fully understood. Mainly used in Type II Diabetes, Metformin is considered to increase insulin sensitivity in vivo, resulting in reduced plasma glucose concentrations, increased glucose uptake, and decreased gluconeogenesis. | The ] of biguanides is not fully understood. Mainly used in Type II Diabetes, Metformin is considered to increase insulin sensitivity in vivo, resulting in reduced plasma glucose concentrations, increased glucose uptake, and decreased gluconeogenesis. | ||
| However, in hyperinsulinemia, biguanides can lower fasting levels of insulin in plasma. Their therapeutic uses derive from their tendency to reduce ] in the liver, and, as a result, reduce the level of glucose in the blood. Biguanides also tend to make the cells of the body more willing to absorb glucose already present in the blood stream, and there again reducing the level of glucose in the plasma. | However, in hyperinsulinemia, biguanides can lower fasting levels of insulin in plasma. Their therapeutic uses derive from their tendency to reduce ] in the liver, and, as a result, reduce the level of glucose in the blood. Biguanides also tend to make the cells of the body more willing to absorb glucose already present in the blood stream, and there again reducing the level of glucose in the plasma. | ||
| ==Side effects and toxicity== | ===Side effects and toxicity=== | ||
| The most common side effect is ] and dyspepsia, occurring in up to 30% of patients. The most important and serious side effect is ], therefore metformin is contraindicated in renal insufficiency. Renal functions should be assessed before starting metformin. Phenformin and buformin are more prone to cause acidosis than metformin; therefore they have been practically replaced by it. However, when metformin is combined with other drugs (combination therapy), ] and other side effects are possible. | The most common side effect is ] and dyspepsia, occurring in up to 30% of patients. The most important and serious side effect is ], therefore metformin is contraindicated in renal insufficiency. Renal functions should be assessed before starting metformin. Phenformin and buformin are more prone to cause acidosis than metformin; therefore they have been practically replaced by it. However, when metformin is combined with other drugs (combination therapy), ] and other side effects are possible. | ||
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| {{reflist}} | {{reflist}} | ||
| * Rang et al., ''Pharmacology'', 5th Edition, 2003, p 388 | |||
| {{oral hypoglycemics}} | {{oral hypoglycemics}} | ||
Revision as of 03:32, 16 March 2014
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| |
| Identifiers | |
|---|---|
| CAS Number | |
| 3D model (JSmol) | |
| Beilstein Reference | 507183 |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.229 
|
| EC Number |
|
| Gmelin Reference | 240093 |
| KEGG | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C2H7N5 |
| Molar mass | 101.113 g·mol |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
Biguanide is the organic compound with the formula HN(C(NH)NH2)2. It is a colourless solid that dissolves in water to give highly basic solution. These solutions slowly hydrolyse to ammonia and urea.
Biguanidine drugs
Biguanidine also refers to a class of drugs based upon the biguanidine molecule. Biguanides can function as oral antihyperglycemic drugs used for diabetes mellitus or prediabetes treatment. They are also used as antimalarial drugs.The disinfectant polyaminopropyl biguanide (PAPB) features biguanide functional groups.
Examples of biguanides:
- Metformin - widely used in treatment of diabetes mellitus type 2
- Phenformin - withdrawn from the market in most countries due to toxic effects
- Buformin - withdrawn from the market due to toxic effects
- Proguanil - an antimalarial drug.
- bioactive biguanidines
-
Metformin, an "unsym"-dimethylbiguanidine
-
Buformin. A butyl derivative of biguanidine.
-
Phenformin. A phenethylated biguanidine.
History
Galega officinalis (French lilac) was used for diabetes treatment in traditional medicine for centuries. In the 1920s, guanidine compounds were discovered in Galega extracts. Animal studies showed that these compounds lowered blood glucose levels. Some less toxic derivatives, synthalin A and synthalin B, were used for diabetes treatment, but after the discovery of insulin they were forgotten for the next several decades. Biguanides were reintroduced into Type 2 diabetes treatment in the late 1950s. Initially phenformin was widely used, but its potential for sometimes fatal lactic acidosis resulted in its withdrawal from pharmacotherapy in most pharmacopeias (in the U.S. in 1977). Metformin has a much better safety profile, and it is the principal biguanide drug used in pharmacotherapy worldwide.
Mechanistic aspects
Biguanides do not affect the output of insulin, unlike other hypoglycemic agents such as sulfonylureas and meglitinides. Therefore, not only are they effective in Type 2 diabetics but they can also be effective in Type 1 patients in concert with insulin therapy.
The mechanism of action of biguanides is not fully understood. Mainly used in Type II Diabetes, Metformin is considered to increase insulin sensitivity in vivo, resulting in reduced plasma glucose concentrations, increased glucose uptake, and decreased gluconeogenesis.
However, in hyperinsulinemia, biguanides can lower fasting levels of insulin in plasma. Their therapeutic uses derive from their tendency to reduce gluconeogenesis in the liver, and, as a result, reduce the level of glucose in the blood. Biguanides also tend to make the cells of the body more willing to absorb glucose already present in the blood stream, and there again reducing the level of glucose in the plasma.
Side effects and toxicity
The most common side effect is diarrhea and dyspepsia, occurring in up to 30% of patients. The most important and serious side effect is lactic acidosis, therefore metformin is contraindicated in renal insufficiency. Renal functions should be assessed before starting metformin. Phenformin and buformin are more prone to cause acidosis than metformin; therefore they have been practically replaced by it. However, when metformin is combined with other drugs (combination therapy), hypoglycemia and other side effects are possible.
References
- Thomas Güthner, Bernd Mertschenk and Bernd Schulz "Guanidine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_545.pub2
- Rang et al., Pharmacology, 5th Edition, 2003, p 388
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