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C1055

Sigma-Aldrich

Cromakalim

Synonym(s):

(±)-trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol

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About This Item

Empirical Formula (Hill Notation):
C16H18N2O3
CAS Number:
94470-67-4
Molecular Weight:
286.33
MDL number:
MFCD00133201
UNSPSC Code:
12352200
PubChem Substance ID:
24891962
NACRES:
NA.77

form

powder

Quality Level

200

storage temp.

2-8°C

SMILES string

CC1(C)Oc2ccc(cc2[C@H]([C@@H]1O)N3CCCC3=O)C#N

InChI

1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m1/s1

InChI key

TVZCRIROJQEVOT-CABCVRRESA-N

Gene Information

rat ... Kcna1(24520) , Kcnj1(24521) , Kcnj5(29713) , Kcnj8(25472)

Application

Cromakalim has been used:
  • as a potassium channel agonist to study its response to an acute increase in downstream pressure in rat lymphatic vessels.
  • as a potassium channel opener to study its effects on the release of transmitters from adrenergic nerves in rat vas deferens.
  • as a potassium channel activator to study its effects on the release of transmitters from purinergic and cholinergic nerves in the rat detrusor muscle.

Biochem/physiol Actions

Cromakalim is an activator of the potassium channel. It is involved in the relaxation of the vascular smooth muscles. Cromakalim exhibits anti-hypertensive activity.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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I Cavero et al.
The Journal of pharmacology and experimental therapeutics, 248(3), 1261-1268 (1989-03-01)
Cromakalim (BRL 34915), a K+ channel activator, and diltiazem relaxed isolated rat aortic rings contracted with a low KCl concentration (25 mM). Gilbenclamide (0.1-3 microM) did not modify base-line resting tension or responses to KCl but prevented the vasorelaxant effects
Xue-Feng Wu et al.
Pain, 152(11), 2605-2615 (2011-09-13)
Adenosine triphosphate-sensitive potassium (K(ATP)) channels are suggested to be involved in pathogenesis of neuropathic pain, but remain underinvestigated in primary afferents and in the spinal cord. We examined alterations of K(ATP) channels in rat spinal cord and tested whether and
P Lijnen et al.
European journal of clinical pharmacology, 37(6), 609-611 (1989-01-01)
The effect of cromakalim, a K(+)-channel activator, on the plasma renin-angiotensin-aldosterone system, catecholamines and alpha-atrial natriuretic peptide, and on the intraerythrocyte concentration and transmembrane fluxes of Na+ and K+ has been investigated in 18 normal male subjects, in a double-blind
W Spinelli et al.
European journal of pharmacology, 179(3), 243-252 (1990-04-25)
The cardiac electrophysiologic effects of the potassium channel activators cromakalim, pinacidil and nicorandil were determined in anesthetized open-chest normotensive dogs using conventional surface electrogram recording techniques. Intravenous administration of cromakalim (0.025-0.5 mg/kg), pinacidil (0.1-2.0 mg/kg) and nicorandil (0.1-2.5 mg/kg) produced
E Grana et al.
European journal of pharmacology, 319(1), 57-64 (1997-01-14)
The present study was carried out to look at the influence of the K+ channel opener cromakalim, compared with suramin and prazosin, on the contractile response evoked by single-pulse field stimulation and exogenous agonists in epididymal and prostatic portions of
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