9569. Tranexamic Acid

Nomenclature

CAS number: 1197-18-8
trans-4-(Aminomethyl)cyclohexanecarboxylic acid; AMCHA; RP-18429; Anvitoff (Abbott); Cyklokapron (Pfizer); Exacyl (Sanofi-Synthelabo); Spiramin (Mitsui); Spotof (CCD); Tranex (Lusofarmaco); Transamin (Daiichi); Ugurol (Rottapharm).
C8H15NO2; mol wt 157.21.
C 61.12%, H 9.62%, N 8.91%, O 20.35%.

Description and references

Antifibrinolytic agent; blocks lysine binding sites of plasminogen. Prepn: A. Einhorn, C. Ladisch, Ann. 310, 194 (1900); M. Levine, R. Sedlecky, J. Org. Chem. 24, 115 (1959); NL 6503605; T. Naito et al., US 3499925 (1965, 1970 to both Daiichi Seiyaku and Mitsubishi Chem.). Pharmacology: Andersson et al., Scand. J. Haematol. 2, 230 (1965). Resoln of isomers and antiplasmin activity: M. Shimizu et al., Chem. Pharm. Bull. 16, 357 (1968), T. Naito et al., ibid., 728. Toxicity data: B. Melander et al., Acta Pharmacol. Toxicol. 22, 340 (1965). Clinical study in treatment of acute upper gastrointestinal tract bleeding: D. Barer et al., N. Engl. J. Med. 308, 1571 (1983); in menorrhagia: J. Bonnar, B. L. Sheppard, Br. Med. J. 313, 579 (1996). Review of pharmacology and therapeutic use: C. J. Dunn, K. L. Goa, Drugs 57, 1005-1032 (1999).

Chemical structure

Properties

mp 386-392° (dec). Soly in water: about 1 g/6 ml. Very slightly sol in alcohol, ether. Practically insol in most other organic solvents. Chemically stable; not hygroscopic. LD50 in mice, rats (mg/kg): 1500, 1200 i.v. (Melander).

Derivative

cis-form.

Nomenclature

CAS number: 1197-17-7

Properties

mp 236-238° (dec).

Therapeutic Category

Hemostatic.

Keywords

Hemostatic