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C1055

Sigma-Aldrich

Cromakalim

Synonyme(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

Formule empirique (notation de Hill):
C16H18N2O3
Numéro CAS:
94470-67-4
Poids moléculaire :
286.33
Numéro MDL:
MFCD00133201
Code UNSPSC :
12352200
ID de substance PubChem :
24891962
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

200

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

TVZCRIROJQEVOT-CABCVRRESA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Xavier Florence et al.
Bioorganic & medicinal chemistry, 19(13), 3919-3928 (2011-06-15)
The synthesis of different series of 4- and 6-substituted R/S-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans is described. All of these new benzopyran derivatives were bearing, at the 4-position, a phenylthiourea moiety substituted on the phenyl ring by a meta or a para-electron-withdrawing group such as
BRL 34915 (cromakalim) activates ATP-sensitive K+ current in cardiac muscle
Sanguinetti M C, et al.
Proceedings of the National Academy of Sciences, 85(21), 8360-8364 (1988)
Cromakalim blocks the purinergic response evoked in rat vas deferens by single-pulse electrical stimulation
Grana E, et al.
European Journal of Pharmacology, 319(1), 57-64 (1997)
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
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