Pinacidil

Pinacidil
Names
	IUPAC name N-cyano-N'-pyridin-4-yl-N''-(1,2,2-trimethylpropyl)guanidine
Identifiers
CAS Number	60560-33-0 (anhydrous) ; 85371-64-8 (monohydrate) ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1159 ; ChEMBL1200338 ;
ChemSpider	4660 ;
ECHA InfoCard	100.056.614
IUPHAR/BPS	2412;
PubChem CID	4826;
UNII	BB4UGO5K0D (anhydrous) ; 7B0ZZH8P2W (monohydrate) ;
CompTox Dashboard (EPA)	DTXSID7048249 ;
	InChI 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) Key: IVVNZDGDKPTYHK-UHFFFAOYSA-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;
	SMILES CC(C(C)(C)C)N=C(NC#N)NC1=CC=NC=C1;
Properties
Chemical formula	C13H19N5
Molar mass	245.32346
Pharmacology
ATC code	C02DG01 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

^ 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.
^ Reynolds, James Blair; Martindale, William L. (1996). The extra pharmacopoeia (31st ed.). London: Royal Pharmaceutical Society. pp. 2739 pages. ISBN 0-85369-342-0.
^ 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 U.S. National Library of Medicine Medical Subject Headings (MeSH)

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

[pmid7473155-1] 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.

[isbn0-85369-342-0-2] 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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Names

IUPAC name N-cyano-N'-pyridin-4-yl-N''-(1,2,2-trimethylpropyl)guanidine
Identifiers
CAS Number	60560-33-0 (anhydrous)^Y 85371-64-8 (monohydrate)^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1159^N ChEMBL1200338^N
ChemSpider	4660^N
ECHA InfoCard	100.056.614
IUPHAR/BPS	2412
PubChem CID	4826
UNII	BB4UGO5K0D (anhydrous)^Y 7B0ZZH8P2W (monohydrate)^Y
CompTox Dashboard (EPA)	DTXSID7048249
InChI 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
SMILES CC(C(C)(C)C)N=C(NC#N)NC1=CC=NC=C1
Properties
Chemical formula	C₁₃H₁₉N₅
Molar mass	245.32346
Pharmacology
ATC code	C02DG01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references