Pinacidil Explained

Pinacidil is a cyanoguanidine drug that opens ATP-sensitive potassium channels producing peripheral vasodilatation of arterioles.[1] It reduces blood pressure and peripheral resistance and produces fluid retention.[2]

Synthesis

Condensation of 4-isothiocyanotopyridine [76105-84-5] (1) and 3,3-dimethyl-2-butanamine [3850-30-4] (2) gives thiourea [67027-06-9] (3). Treatment of that intermediate with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine leads to the unsymmetrical carbodiimide, CID:20501933 (4'). Addition of cyanamid affords pinacidil (5).

Notes and References

  1. Gollasch M, Bychkov R, Ried C, Behrendt F, Scholze S, Luft FC, Haller H . Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells . J. Pharmacol. Exp. Ther. . 275 . 2 . 681–92 . 1995 . 7473155 .
  2. Book: Reynolds, James Blair . Martindale, William L. . The extra pharmacopoeia . Royal Pharmaceutical Society . London . 1996 . 31st . 2739 pages . 0-85369-342-0 . registration .