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Merck
CN

P154

Pinacidil monohydrate

powder

Synonym(s):

(±)-N-Cyano-N′-4-pyridinyl-N″-(1,2,2-trimethylpropyl)guanidine monohydrate

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About This Item

Empirical Formula (Hill Notation):
C13H19N5 · H2O
CAS Number:
85371-64-8
Molecular Weight:
263.34
NACRES:
NA.77
PubChem Substance ID:
24277866
UNSPSC Code:
12352106
EC Number:
262-294-9
MDL number:
MFCD00242745

Key Documents

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InChI key

AFJCNBBHEVLGCZ-UHFFFAOYSA-N

InChI

1S/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

SMILES string

O.CC(N\C(Nc1ccncc1)=N\C#N)C(C)(C)C

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 40 mg/mL

Quality Level

200

Gene Information

human ... ABCC9(10060), KCNJ11(3767)
mouse ... Kcnj11(16514)
rat ... Kcna1(24520), Kcnj1(24521), Kcnj11(83535), Kcnj5(29713), Kcnj8(25472)

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Application

Pinacidil monohydrate has been used:
  • in repolarization studies by infusing into left anterior descending artery (LAD)
  • to induce ATP-sensitive K+ (KATP) current in ventricular myocytes for electrophysiological studies
  • as a KATP opener to treat myocardial cells

Biochem/physiol Actions

K+ channel activator; antihypertensive.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000532960
0000532960
0000490113
0000490113
0000365854

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Ivana Barbaric et al.
Cryobiology, 63(3), 298-305 (2011-10-27)
Human embryonic stem cells (hESCs) can be maintained as undifferentiated cells in vitro and induced to differentiate into a variety of somatic cell types. Thus, hESCs provide a source of differentiated cell types that could be used to replace diseased
Jing Xu et al.
Journal of cardiovascular pharmacology, 59(6), 514-522 (2012-02-22)
We investigated the beneficial effect of pinacidil pretreatment on vascular reactivity, calcium sensitivity, and animal survival after hemorrhagic shock, its relationship to protein kinase Cα (PKCα), protein kinase Cε (PKCε), and adenosine. Using hemorrhagic shock rats, the protective effects of
Electrophysiological analyses of transgenic mice overexpressing KCNJ8 with S422L mutation in cardiomyocytes
Watanabe Y, et al.
Journal of Pharmacological Sciences, 135(1), 37-43 (2017)
Jeanne G van der Waal et al.
Frontiers in physiology, 12, 737609-737609 (2021-11-09)
Background: The detection and localization of electrophysiological substrates currently involve invasive cardiac mapping. Electrocardiographic imaging (ECGI) using the equivalent dipole layer (EDL) method allows the noninvasive estimation of endocardial and epicardial activation and repolarization times (AT and RT), but the
Protective actions of epoxyeicosatrienoic acid: dual targeting of cardiovascular PI3K and KATP channels
Bodiga S, et al.
Journal of Molecular and Cellular Cardiology, 46(6), 978-988 (2009)
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