Pinacidil

Pinacidil
Names
IUPAC name
N-cyano-N'-pyridin-4-yl-N''-(1,2,2-trimethylpropyl)guanidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.056.614 Edit this at Wikidata
UNII
  • InChI=1S/C13H19N5/c1-10(13(2,3)4)17-12(16-9-14)18-11-5-7-15-8-6-11/h5-8,10H,1-4H3,(H2,15,16,17,18) ☒N
    Key: IVVNZDGDKPTYHK-UHFFFAOYSA-N ☒N
  • InChI=1/C13H19N5/c1-10(13(2,3)4)17-12(16-9-14)18-11-5-7-15-8-6-11/h5-8,10H,1-4H3,(H2,15,16,17,18)
    Key: IVVNZDGDKPTYHK-UHFFFAOYAY
  • CC(C(C)(C)C)N=C(NC#N)NC1=CC=NC=C1
Properties
C13H19N5
Molar mass 245.32346
Pharmacology
C02DG01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

Thieme Synthesis:[3][4][5] Patents:[6][7]

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).

References

  1. ^ Gollasch M, Bychkov R, Ried C, Behrendt F, Scholze S, Luft FC, Haller H (1995). "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. PMID 7473155.
  2. ^ Reynolds, James Blair; Martindale, William L. (1996). The extra pharmacopoeia (31st ed.). London: Royal Pharmaceutical Society. pp. 2739 pages. ISBN 0-85369-342-0.
  3. ^ Petersen, Hans Joergen; Nielsen, C. Kaergaard; Arrigoni-Martelli, E. (1978). "Synthesis and hypotensive activity of N-alkyl-N-cyano-N'-pyridylguanidines". Journal of Medicinal Chemistry 21 (8): 773–781. doi:10.1021/jm00206a011.
  4. ^ Hansen, E. T.; Petersen, H. J. (2006). "Synthesis ofN-Alkyl-N'-cyano-N″-4-pyridylguanidines from 4-Pyridyldithiocarbamic AcidviaN-Alkyl-N′-4-Pyridylthioureas, orvia4-Pyridylcyaniminothiocarbamic Acid". Synthetic Communications. 14 (13): 1275–1283. doi:10.1080/00397918408076809.
  5. ^ Zhang, Hao; Liu, Rui-Quan; Liu, Ke-Chang; Li, Qi-Bo; Li, Qing-Yang; Liu, Shang-Zhong (2014). "A One-Pot Approach to Pyridyl Isothiocyanates from Amines". Molecules 19(9): 13631–13642. doi:10.3390/molecules190913631.
  6. ^ Hans J. Petersen, USRE31244E (1983 to Leo Pharma AS).
  7. ^ Hans Jorgen Petersen, U.S. patent 4,057,636 (1977 to Leo Pharma AS).


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