432. ε-Aminocaproic Acid

Nomenclature

CAS number: 60-32-2
6-Aminohexanoic acid; epsilon-aminocaproic acid; epsilcapramin; EACA; CY-116; Amicar (Wyeth); Epsikapron (Pharmacia); Hemocaprol (Sanofi-Aventis).
C6H13NO2; mol wt 131.17.
C 54.94%, H 9.99%, N 10.68%, O 24.39%.

Description and references

Antifibrinolytic; inhibits the activity of plasmin and plasminogen, q.q.v. Prepn: S. Gabriel, T. A. Maass, Ber. 32, 1266 (1899); A. Galat, S. Mallin, J. Am. Chem. Soc. 68, 2729 (1946); C. Y. Meyers, L. E. Miller, Org. Synth. coll. vol. IV, 39 (1963). Toxicity data: D. W. Hallesy et al., Pharmacologist 3, 62 (1961). Crystal structure: G. Bodor et al., Acta Crystallogr. 23, 482 (1967). Clinical trial and mode of action study: T. J. Vander Salm et al., J. Thorac. Cardiovasc. Surg. 112, 1098 (1996).

Chemical structure

Properties

Crystals from alcohol, mp 202-203°. pK1 4.43; pK2 10.75. Freely sol in water; sparingly in methanol. Practically insol in ethanol, chloroform. LD50 in rats (g/kg): 7.0 i.p.; ≈3.3 i.v. (Hallesy).

Derivative

Hydrochloride.

Nomenclature

CAS number: 4321-58-8
C6H13NO2.HCl; mol wt 167.63.
C 42.99%, H 8.42%, N 8.36%, O 19.09%, Cl 21.15%.

Properties

mp 128-129°.

Therapeutic Category

Hemostatic.

Keywords

Hemostatic