Himbacine is a piperidine alkaloid with a tricyclic lactone scaffold isolated from Galbulimima sp. (Himantandra sp.) by Ritchie and Taylor, University of Sydney, Australia in 1956. Himbacine is a potent M2 muscarinic receptor antagonist with selectivity for cardiac receptors and a thrombin (PAR1) receptor inhibitor. Its analog, vorapaxar is marketed for secondary prevention of thrombotic cardiovascular events.
| Molecular Formula | C22H35NO2 |
| References | Anwar-ul S et al (1986) The cardio-selectivity of himbacine: a muscarine receptor antagonist. ., Naunyn Schmiedebergs Arch. Pharmacol. 332:16 Brown FFC et al (1956) The chemical constituents of Himantandra species. II. The isolation of the alkaloids of Himantandra baccata Bail. and H. belgraveana F .Muell. Aust. J. Chem. 9:283 Chackalamannil S et al (2008) Discovery of a novel, orally active himbacine-based thrombin receptor antagonist (SCH 530348) with potent antiplatelet activity. J. Med. Chem. 51:3061 Darroch SA et al (1990) Structure-activity relationships of some Galbulimima alkaloids related to himbacine. Eur. J. Pharmacol. 182:131 Mander LN et al (1967) The chemical constituents of Galbulimima species IX. The structures of himbadine and alkaloid G.B. 13. Aust. J. Chem. 20:1473 Willis AC et al (2006) The absolute stereochemistry of the Galbulimima alkaloids. Aust. J. Chem. 59:629 |