Biguanide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Biguanide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Biguanide?

The molecule Biguanide presents a molecular formula of C2H7N5 and its IUPAC name is 1-(diaminomethylidene)guanidine.

A biguanide is a molecule with a structure based on two nitrogen atoms, each of which is bonded to a carbon atom. The most well-known biguanide is metformin, which is used as a medication for type 2 diabetes. Biguanides work by inhibiting the production of glucose by the liver, and also by increasing the sensitivity of cells to insulin..

There are several other biguanides that have been developed, but metformin is by far the most widely used. Some of the other biguanides that have been studied include phenformin, buformin, and hydroxyurea. While these molecules have different structures, they all share the common feature of two nitrogen atoms bonded to a carbon atom..

Biguanides have a long history of use in the treatment of diabetes. The first biguanide to be used medicinally was phenformin, which was introduced in the 1950s. However, phenformin was associated with a high incidence of side effects, including lactic acidosis, and was withdrawn from the market in the 1970s..

Metformin was introduced in the 1970s and has been used safely and effectively for the treatment of type 2 diabetes ever since. Metformin is usually well tolerated, with the most common side effects being gastrointestinal upset and diarrhea..

Biguanides are an important class of molecules with a wide range of applications. Metformin is the most well-known biguanide, but there are several other molecules in this class with different structures and properties. Biguanides are used medicinally to treat diabetes, and they have also been studied for their potential use in cancer treatment..

3D structure

Cartesian coordinates

Geometry of Biguanide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Biguanide XNCOSPRUTUOJCJ-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Biguanide

 

Molecule descriptors

 
IUPAC name1-(diaminomethylidene)guanidine
InChI codeInChI=1S/C2H7N5/c3-1(4)7-2(5)6/h(H7,3,4,5,6,7)
InChI KeyXNCOSPRUTUOJCJ-UHFFFAOYSA-N
SMILESN=C(N)NC(=N)N

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 056B031
  • 1,2,3-triimidodicarbonic diamide
  • 1-(diaminomethylidene)guanidine
  • 4911-98-2
  • 56-03-1
  • A830895
  • AI3-52571
  • Biguanide
  • Biguanides
  • C07672
  • DB13100
  • DIGUANIDE
  • DURAPLUS
  • FB4Q52I9K2
  • FT-0659014
  • GUANIDINE, (AMINOIMINOMETHYL)-
  • Guanylguanidine
  • H2N-C(=NH)-NH-C(=NH)-NH2
  • HBIG
  • ISOBIGUANIDE
  • Imidodicarbonimidic diamide
  • Q142880
  • [(diaminomethylidene)amino]methanimidamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097424
  • UNII-FB4Q52I9K2
  • AKOS006273502
  • AKOS015894538
  • DTXSID7074664
  • CHEMBL4297654
  • CHEBI:3095
  • EINECS 200-251-8
  • SCHEMBL8039

Physico-Chemical properties

IUPAC name1-(diaminomethylidene)guanidine
Molecular formulaC2H7N5
Molecular weight101.11
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity27.13
LogP0.4
Topological polar surface area111.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.