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P154

Sigma-Aldrich

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
EC Number:
262-294-9
MDL number:
MFCD00242745
UNSPSC Code:
12352106
PubChem Substance ID:
24277866
NACRES:
NA.77

form

powder

Quality Level

200

color

white to beige

solubility

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

SMILES string

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

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

InChI key

AFJCNBBHEVLGCZ-UHFFFAOYSA-N

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Jun-Yih Chen et al.
Shock (Augusta, Ga.), 38(2), 203-212 (2012-05-12)
Alterations in the activity of vascular K channels are commonly associated with abnormalities in cerebral vascular function after subarachnoid hemorrhage (SAH). Subarachnoid hemorrhage-induced vasospasm remains incompletely understood; nevertheless, activation of K channels may be of benefit in relieving spastic constriction.
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