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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:
Molecular Weight:
286.33
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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

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 Code

11 - Combustible Solids

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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Omonkhelin J Owolabi et al.
Journal of diabetes, 5(1), 88-94 (2013-02-05)
Levcromakalim is a vasorelaxant used in the management of hypertension in diabetes mellitus. Thus, the effects of levcromakalim were investigated in streptozotocin (STZ)-diabetic rats. Diabetes was induced in Wistar albino rats with a single injection of STZ (60 mg/kg, i.p.)
C Boselli et al.
European journal of pharmacology, 335(1), 23-30 (1997-11-26)
Contraction of the rat detrusor muscle is mediated by cholinergic and purinergic mechanisms. The present study was carried out to look at the influence of cromakalim, compared with atropine, suramin and nifedipine on the contractile response evoked by single shock
Aravind R Gade et al.
Molecular pharmacology, 83(1), 294-306 (2012-11-02)
The ATP-sensitive potassium channel (K(ATP)) in mouse colonic smooth muscle cell is a complex containing a pore-forming subunit (Kir6.1) and a sulfonylurea receptor subunit (SUR2B). These channels contribute to the cellular excitability of smooth muscle cells and hence regulate the
Vasorelaxant effects of cromakalim in rats are mediated by glibenclamide-sensitive potassium channels.
Cavero I, et al.
Journal of Pharmacology and Experimental Therapeutics, 248(3), 1261-1268 (1989)
M C Sanguinetti et al.
Proceedings of the National Academy of Sciences of the United States of America, 85(21), 8360-8364 (1988-11-01)
The mechanism by which the antihypertensive agent BRL 34915 (cromakalim) affects action potential duration (APD) and effective refractory period (ERP) in isolated cardiac muscle was investigated. BRL 34915 (greater than or equal to 3 microM) shortened ERP of ferret (Mustela

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