Biguanidine

Biguanide

Identifiers
CAS Number	56-03-1 Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	507183
ChEBI	CHEBI:3095 Y
ChemSpider	5726 Y
ECHA InfoCard	100.000.229
EC Number	200-251-8
Gmelin Reference	240093
KEGG	C07672 Y
PubChem CID	5939
InChI InChI=1S/C2H7N5/c3-1(4)7-2(5)6/h(H7,3,4,5,6,7) Y Key: XNCOSPRUTUOJCJ-UHFFFAOYSA-N Y
SMILES [nH]:c(:[nH2]):[nH]:c(:[nH]):[nH2] NC(=N)NC(N)=N
Properties
Chemical formula	C2H7N5
Molar mass	101.11 g·mol−1
Acidity (pKa)	3.07, 13.25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Biguanide (/baɪˈɡwɒnaɪd/) is the organic compound with the formula HN(C(NH)NH₂)₂. It is a colorless solid that dissolves in water to give highly basic solution. These solutions slowly hydrolyse to ammonia and urea.

A variety of derivatives of biguanide are used as pharmaceutical drugs.

The term "biguanidine" often refers specifically to a class of drugs that function as oral antihyperglycemic drugs used for diabetes mellitus or prediabetes treatment.

Examples include:

Metformin, anassymetric dimethylbiguanidine

Buformin. A butyl derivative of biguanidine.

Phenformin. A phenethylated biguanidine.

Galega officinalis (French lilac) was used in diabetes treatment 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, their use declined. 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 most pharmacopeias (in the U.S. in 1978). Metformin has a much better safety profile, and it is the principal biguanide drug used in pharmacotherapy worldwide.