441. Aminoguanidine

Nomenclature

CAS number: 79-17-4
Hydrazinecarboximidamide; guanylhydrazine; pimagedine.
CH6N4; mol wt 74.09.
C 16.21%, H 8.16%, N 75.62%.

Description and 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).

Chemical structure

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

Hydrochloride.

Nomenclature

CAS number: 1937-19-5
GER-11.
CH6N4.HCl; mol wt 110.55.
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.

Therapeutic Category

In prevention and treatment of chronic diabetic complications.