Aminoguanidine

Title: Aminoguanidine
CAS Registry Number: 79-17-4
CAS Name: Hydrazinecarboximidamide
Additional Names: guanylhydrazine; pimagedine
Molecular Formula: CH6N4
Molecular Weight: 74.09
Percent Composition: C 16.21%, H 8.16%, N 75.62%
Literature References: Nucleophilic hydrazine; inhibits the formation of advanced glycosylation end products (AGEs) that have been implicated in the etiology of diabetic complications. Prepn: J. Thiele, Ann. 270, 1 (1892); G. B. L. Smith, E. Anzelmi, J. Am. Chem. Soc. 57, 2730 (1935). Review of chemistry of aminoguanidine and related compounds: E. Lieber, G. B. L. Smith, Chem. Rev. 25, 213-271 (1939); of preparative methods: F. Kurzer, L. E. A. Godfrey, Chem. Ind. (London) 1962, 1584-1595. Prevention of glucose-derived aortic collagen cross-linking in diabetic rats: M. Brownlee et al., Science 232, 1629 (1986). Mechanism of action study: D. Edelstein, M. Brownlee, Diabetes 41, 26 (1992). Review of therapeutic potential: B. H. R. Wolffenbuttel, M. S. P. Huijberts, Neth. J. Med. 42, 205-208 (1993).
Properties: Crystals. Sol in water, alc. Practically insol in ether. Aq soln is strongly alkaline and reddens on standing in air; ammonia is evolved on heating.
Derivative Type: Hydrochloride
CAS Registry Number: 1937-19-5
Manufacturers' Codes: GER-11
Molecular Formula: CH6N4.HCl
Molecular Weight: 110.55
Percent Composition: C 10.86%, H 6.38%, N 50.68%, Cl 32.07%
Properties: Large prisms from dil alc, mp 163°. Very sol in water; sol in alc. Practically insol in ether.
Melting point: mp 163°
Therap-Cat: In prevention and treatment of chronic diabetic complications.
Aminometradine Aminopentamide Aminophylline Aminopromazine Aminopropylon

Pimagedine
Skeletal formula of a pimagedine with all hydrogens added Spacefill model of a pimagedine
Identifiers
CAS number 79-17-4 YesY
PubChem 2146
ChemSpider 2061 N
UNII SCQ4EZQ113 N
ChEMBL CHEMBL225304 YesY
Jmol-3D images Image 1
Properties
Molecular formula CH6N4
Molar mass 74.09 g mol−1
Density 1.72 g/ml
Boiling point 261 °C; 502 °F; 534 K
log P −1.475
Related compounds
Related compounds Guanidine
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Pimagedine, also known as aminoguanidine, is an investigational drug for the treatment of diabetic nephropathy that is no longer under development as a drug.[1] Pimagedine is a diamine oxidase and nitric oxide synthase inhibitor. It acts to reduce levels of advanced glycation end products (AGEs) through interacting with 3-deoxyglucosone.