4718. Hirudin

Nomenclature

CAS number: 8001-27-2
Exhirud (Sanofi Winthrop); Hirudex (Cooper).

Description and references

Anticoagulant protein extracted from the salivary glands of the medicinal leech, Hirudo medicinalis Linn. Hirudin is a single chain polypeptide containing 65 amino acids; mol wt approximately 7000 daltons. Several isoforms have been identified. A specific inhibitor of thrombin, q.v., hirudin does not require the presence of other coagulation factors. Isoln: J. B. Haycraft, Arch. Exp. Pathol. Pharmakol. 18, 209 (1884). Initial characterization: F. Markwardt, Naturwissenschaften 42, 537 (1955). Improved isoln: P. Walsmann, F. Markwardt, Thromb. Res. 40, 563 (1985). Amino acid sequence: T. E. Petersen et al. in Protides of the Biological Fluids vol. 23, H. Peeters, Ed. (Pergamon Press, London, 1976) pp 145-149. Antithrombin activity: F. Markwardt, Methods Enzymol. 19, 924 (1970). Pharmacokinetics in humans: F. Markwardt et al., Thromb. Haemostasis 52, 160 (1984). Chromogenic assay in plasma: U. Griessbach et al., Thromb. Res. 37, 347 (1985). Series of articles on development, pharmacology, and therapeutic potential of natural and recombinant hirudins: Semin. Thromb. Hemostasis 15, 261-333 (1989). Review of pharmacology and therapeutic potential: P. H. Johnson, Annu. Rev. Med. 45, 165-177 (1994); of therapeutic use in myocardial infarction: U. Zeymer, K.-L. Neuhaus, Drug Saf. 12, 234-239 (1995).

Properties

Gray or white flakes or powder. pI 3.9. Sol in water, physiol saline soln, in pyridine. Practically insol in alcohol, ether, acetone, benzene. Deteriorates on storage in sealed ampuls, on exposure to heat and when in soln with dil acids.

Derivative

Desirudin.

Nomenclature

CAS number: 120993-53-5
63-Desulfohirudin (Hirudo medicinalis isoform HV1); ds-hirudin; CGP-39393; Revasc (Aventis).

Description and references

Identical in amino acid sequence to natural hirudin variant 1 (HV1) except that it lacks a sulfate group on Tyr at residue 63. Production by recombinant DNA technology: M. Liersch et al., EP 168342 (1986 to Ciba-Geigy); eidem, US 5422249 (1995 to Ciba-Geigy; UCP Gen-Pharma); E. Fortkamp et al., DNA 5, 511 (1986); J. Dodt et al., FEBS Lett. 202, 373 (1986). Physicochemical properties: A. Electricwala et al., Thromb. Haemostasis 63, 499 (1990). Clinical pharmacology: M. Verstraete et al., J. Am. Coll. Cardiol. 22, 1080 (1993). Clinical trial in coronary angioplasty: A. A. van den Bos et al., Circulation 88, 2058 (1993); in acute coronary syndromes: E. J. Topol et al., N. Engl. J. Med. 335, 775 (1996).

Derivative

Lepirudin.

Nomenclature

CAS number: 138068-37-8
1-l-Leucine-2-l-threonine-63-desulfohirudin (Hirudo medicinalis isoform HV1); HBW-023; Refludan (Aventis).

Description and references

Peptide of 65 amino acids produced by recombinant DNA technology. Prepn: P. Crause et al., EP 324712; eidem, US 5180668 (1989, 1993 both to Hoechst AG). Clinical pharmacology: H. J. Roethig et al., Int. Congr. Ser. 944, 227 (1991). Clinical trial as adjunctive therapy with TPA: U. Zeymer et al., Am. J. Cardiol. 76, 997 (1995); in heparin-induced thrombocytopenia: F. Schiele et al., Am. J. Hematol. 50, 20 (1995).

Therapeutic Category

Antithrombotic.

Keywords

Anticoagulant