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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

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

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_germany

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
0000365854
0000356885
0000356886
0000356884
0000345739

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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.
Milla Mikkola et al.
Stem cells and development, 22(5), 707-716 (2012-10-31)
Lectins are carbohydrate-binding proteins, which occur ubiquitously in nature and are abundant in all living organisms from bacteria to mammals. They have several biological functions among which cell adhesion is well known and characterized. Based on the characterization of 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)
Asami Mori et al.
European journal of pharmacology, 669(1-3), 94-99 (2011-08-30)
The large-conductance Ca(2+)-activated K(+) (BK(Ca)) channels modulate the retinal vascular tone, but question of whether the impairment of the channel function contributes to abnormalities of retinal circulation has not yet been completely elucidated. The purpose of this study was to
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
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