Chemistry:Pinacidil
From HandWiki
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| IUPAC name
N-cyano-N'-pyridin-4-yl-N''-(1,2,2-trimethylpropyl)guanidine
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C13H19N5 | |
| Molar mass | 245.32346 |
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| 1=ATC code }} | 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
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
- ↑ "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. PMID 7473155. http://jpet.aspetjournals.org/cgi/content/abstract/275/2/681.
- ↑ Reynolds, James Blair; Martindale, William L. (1996). The extra pharmacopoeia (31st ed.). London: Royal Pharmaceutical Society. pp. 2739 pages. ISBN 0-85369-342-0. https://archive.org/details/martindaleextrap00will/page/2739.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Hans J. Petersen, USRE31244E (1983 to Leo Pharma AS).
- ↑ Hans Jorgen Petersen, U.S. Patent 4,057,636 (1977 to Leo Pharma AS).
External links
- Pinacidil at the US National Library of Medicine Medical Subject Headings (MeSH)
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