85371-64-8

Basic information

• Product Name: Pinacidil
• Synonyms: (+/-)-N-Cyano-N'-4-pyridinyl-N''-(1,2,2-trimethylpropyl)guanidine;Pinacidil;(±)-N-Cyano-N’-4-pyridinyl-N’’-(1，2，2-trimethylpropyl)guanidine monohydrate;Hndac;Guanidine, N-cyano-N'-4-pyridinyl-N''-(1,2,2-trimethylpropyl)-, monohydrate;Pinacidil Hydrate
• CAS NO: 85371-64-8
• Molecular Formula: C₁₃H₁₉N₅
• Molecular Weight: 263.34
• EINECS: 262-294-9
• Product Categories: INOCOR
• Mol File: 85371-64-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 164-165°
• Boiling Point: 356.7°C at 760 mmHg
• Flash Point: 169.5°C
• Appearance: white/solid
• Vapor Pressure: 2.87E-05mmHg at 25°C
• Storage Temp.: RT
• Solubility: ethanol: 14 mg/mL
• PKA: pKa 空 (Uncertain)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: Pinacidil(CAS DataBase Reference)
• NIST Chemistry Reference: Pinacidil(85371-64-8)
• EPA Substance Registry System: Pinacidil(85371-64-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 85371-64-8(Hazardous Substances Data)

Usage

Description

Pinacidil is a peripheral vasodilator, primarily used in the management of arterial hypertension of varying degrees, often in combination with a diuretic or beta-blocker. Its hypotensive effect is believed to be due to the activation of potassium channels.

Uses

Used in Pharmaceutical Industry:
Pinacidil is used as an antihypertensive agent for managing arterial hypertension of all degrees, typically in combination with a diuretic or beta-blocker.
Used in Cardiology Research:
Pinacidil is used as a KATP opener to treat myocardial cells, aiding in the study of repolarization and electrophysiological properties of the heart.
Used in Electrophysiological Studies:
Pinacidil is used to induce ATP-sensitive K+ (KATP) current in ventricular myocytes, contributing to a better understanding of cardiac electrophysiology and the development of treatments for related conditions.

Originator

Leo (Denmark)

Biochem/physiol Actions

Pinacidil is a KATP channel agonist. It protects cardiomyocytes by preventing loss of mitochondrial membrane potential. It prevents the caspase 3 activation in hypoxia/reoxygenation injury.

References

1) Hermsmeyer et al. (1988), Pinacidil actions on ion channels in vascular muscle; J. Cardiovasc. Pharmacol., 12(Suppl. 2) S17 2) Gollasch et al. (1995), Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells; J. Pharmacol. Exp. Therap., 275 681 3) Cohen & Kurz (1988), Pinacidil-induced vascular relaxation: comparison to other vasodilators and to classical mechanisms of vasodilation; J. Cardiovasc. Pharmacol., 12(Suppl. 2) S5 4) Teshima et al. (2003), Mitochondrial ATP-sensitive potassium channel activation protects cerebellar granule neurons from apoptosis induced by oxidative stress; Stroke, 34 1796 5) Xie et al. (2010), K(ATP) channel openers protect mesencephalic neurons against MPP+-induced cytotoxicity via inhibition of ROS protection; J. Neurosci. Res., 88 428 6) Zhang et al. (2008), Effects of ATP sensitive potassium channel opener on the mRNA and protein expressions of caspase-12 after cerebral ischemia-reperfusion in rats; Neurosci. Bull., 24 7

InChI:InChI=1/C13H19N5.H2O/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);1H2

Upstream product

• 420-04-2 CYANAMID 
• 67027-06-9 1-Pyridin-4-yl-3-(1,2,2-trimethyl-propyl)-thiourea 
• 100-48-1 pyridine-4-carbonitrile 
• 53561-77-6 1,2,2-trimethylpropyl amine hydrochloride 

Relevant articles and documents

De novodesign and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions

Described here is thede novodesign and synthesis of a series of 6H-dipyrido[1,2-e:2′,1′-i]purin-6-ones (DPs) as a new class of visible-light photoredox catalysts (PCs). The synthesizedDP1-5showed theirλAbs(max)values in 433-477 nm, excited state redox potentials in 1.15-0.69 eV and ?1.41 to ?1.77 eV (vs.SCE), respectively. As a representative,DP4enables the productive guanylation of various amines, including 1°, 2°, and 3°-alkyl primary amines, secondary amines, aryl and heteroaryl amines, amino-nitrile, amino acids and peptides as well as propynylamines and α-amino esters giving diversities in biologically important guanidines and cyclic guanidines. The photocatalytic efficacy ofDP4in the guanylation overmatched commonly used Ir and Ru polypyridyl complexes, and some organic PCs. Other salient merits of this method include broad substrate scope and functional group tolerance, gram-scale synthesis, and versatile late-stage derivatizations that led to a derivative81exhibiting 60-fold better anticancer activity against Ramos cells with the IC50of 0.086 μM than that of clinical drug ibrutinib (5.1 μM).