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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N2O6P.2Na
Molecular Weight 410.2693
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Foslevcromakalim sodium

SMILES

[Na+].[Na+].CC1(C)OC2=CC=C(C=C2[C@H]([C@@H]1OP([O-])([O-])=O)N3CCCC3=O)C#N

InChI

InChIKey=HQRIFHGJGBFZSE-AMTWEWDESA-L
InChI=1S/C16H19N2O6P.2Na/c1-16(2)15(24-25(20,21)22)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)23-16;;/h5-6,8,14-15H,3-4,7H2,1-2H3,(H2,20,21,22);;/q;2*+1/p-2/t14-,15+;;/m1../s1

HIDE SMILES / InChI
Cromakalim is an ATP-sensitive potassium (KATP) channel opener, which was studied for the treatment of gastric ulcer, hypertension and preventing a cardiomyopathy. But the development of this drug was discontinued due to heart lesions found in monkey chronic toxicity studies.

Approval Year

PubMed

PubMed

TitleDatePubMed
Shear stress increases expression of a KATP channel in rat and bovine pulmonary vascular endothelial cells.
2003-10
The role of K+ channels in vasorelaxation induced by hypoxia and the modulator effects of lidocaine in the rat carotid artery.
2003-08
Effect of acute hypoxia on ATP-sensitive potassium currents in substantia gelatinosa neurons of juvenile rats.
2003-08
Antiulcer activity of levcromakalim and nicorandil in albino rats: a comparative study.
2003-07-15
Differential role of PTK and ERK MAPK in superoxide impairment of K(ATP) and K(Ca) channel cerebrovasodilation.
2003-07
Differential antivasoconstrictor effects of levcromakalim and rilmakalim on the isolated human mammary artery and saphenous vein.
2003-06
Defibrillatory action of glibenclamide is independent from ATP-sensitive K+ channels and free radicals.
2003-06
Mitochondrial K ATP channel activation is important in the antiarrhythmic and cardioprotective effects of non-hypotensive doses of nicorandil and cromakalim during ischemia/reperfusion: a study in an intact anesthetized rabbit model.
2003-06
Role of cyclooxygenase-1 and -2, phospholipase C, and protein kinase C in prostaglandin-mediated gastroprotection.
2003-06
Increased superoxide dismutase and Na+, K+-ATPase activities in aortic strips from potassium-adapted rats: implication for altered vascular reactivity.
2003-05
Dualistic actions of cromakalim and new potent 2H-1,4-benzoxazine derivatives on the native skeletal muscle K ATP channel.
2003-05
Effect of hypoxia on vasodilator responses to S-nitroso-N-acetylpenicillamine and levcromakalim in guinea pig basilar artery.
2003-05
Potassium channel activators based on the benzopyran substructure: synthesis and activity of the C-8 substituent.
2003-04-17
Coronary myogenic constriction antagonizes EDHF-mediated dilation: role of KCa channels.
2003-04
Dual effect of agmatine in the bisected rat vas deferens.
2003-03
Differential effects of ascorbate on endothelium-derived hyperpolarizing factor (EDHF)-mediated vasodilatation in the bovine ciliary vascular bed and coronary artery.
2003-03
[Analyses of Ca-related ion channel currents and their involvement in Ca mobilization in smooth muscle and endothelial cells].
2003-03
Mexiletine differentially modulates vasorelaxation mediated by adenosine triphosphate-sensitive K+ channels in aortas from normotensive and hypertensive rats.
2003-03
Contractile responses of the human umbilical artery to KCl and serotonin in Ca-free medium and the effects of levcromakalim.
2003-02-07
Apamin inhibits NO-induced relaxation of the spontaneous contractile activity of the myometrium from non-pregnant women.
2003-02-05
[Effect of levcromakalim and cromakalim on ATP-sensitive K+ channel of pulmonary arterial smooth muscle cells in pulmonary hypertensive rats].
2003-02
Differential effects of sulphonylureas on the vasodilatory response evoked by K(ATP) channel openers.
2003-02
In vivo evaluation of the potency and bladder-vascular selectivity of the ATP-sensitive potassium channel openers (-)-cromakalim, ZD6169 and WAY-133537 in rats.
2003-02
Inhibition of cromakalim-activated K+ current by ethanol in follicle-enclosed Xenopus oocytes.
2003-01
Inhibitory effects of etomidate and ketamine on adenosine triphosphate-sensitive potassium channel relaxation in canine pulmonary artery.
2003-01
Effects of ATP-sensitive K+ channel openers and tolterodine on involuntary bladder contractions in a pig model of partial bladder outlet obstruction.
2003
Alterations in KATP and KCa channel function in cerebral arteries of insulin-resistant rats.
2002-12
Ketamine stereoselectively affects vasorelaxation mediated by ATP-sensitive K(+) channels in the rat aorta.
2002-10
Fluorescence-based functional assay for sarcolemmal ATP-sensitive potassium channel activation in cultured neonatal rat ventricular myocytes.
2002-08-08
Molecular modeling and QSAR studies on K(ATP) channel openers of the benzopyran type.
2002-08
Effects of chronic treatment with cromakalim and glibenclamide in alloxan-induced diabetic rats.
2002-08
Synthesis and vasorelaxant activity of new 1,4-benzoxazine derivatives potassium channel openers.
2002-08
Protein tyrosine kinase and mitogen-activated protein kinase activation contribute to K(ATP) and K(ca) channel impairment after brain injury.
2002-07-12
Involvement of K+ channels in adenosine A2A and A2B receptor-mediated hyperpolarization of porcine coronary artery endothelial cells.
2002-07
Potassium channels and human corporeal smooth muscle cell tone: diabetes and relaxation of human corpus cavernosum smooth muscle by adenosine triphosphate sensitive potassium channel openers.
2002-07
Modified ionic models of cardiac tissue for efficient large scale computations.
2002-06-07
The novel diazoxide analog 3-isopropylamino-7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener.
2002-06
Active relaxation of human gallbladder muscle is mediated by ATP-sensitive potassium channels.
2002
Involvement of ATP-sensitive potassium channels in a model of a delayed vascular hyporeactivity induced by lipopolysaccharide in rats.
1999-07
Glibenclamide-sensitive hypotension produced by helodermin assessed in the rat.
1998-12
Role of potassium channels in halothane-epinephrine arrhythmias.
1998-06
K+ channel openers delay intestinal transit and have antidiarrheal activity.
1995-12-12
Cellular localization of the inhibitory action of relaxin against uterine spasm.
1995-12
Effect of four potassium channel agonists on bupivacaine-induced toxicity in mice.
1995
Effects of potassium channel modulation during global ischaemia in isolated rat heart with and without cardioplegia.
1992-11
Effects of NG-nitro-L-arginine methyl ester on vasodilator responses to adrenaline or BRL 38227 in conscious rats.
1991-11
Effects of cromakalim and pinacidil on large epicardial and small coronary arteries in conscious dogs.
1990-11
Preclinical pharmacology of Ro 31-6930, a new potassium channel opener.
1990-02
Effects of pinacidil and cromakalim (BRL 34915) on bladder function in rats with detrusor instability.
1989-10
The relaxant action of BRL 34915 in rat uterus.
1987-08
Patents

Sample Use Guides

Eight patients with moderately severe asthma were given 0.125, 0.25, and 0.5 mg of Levcromakalim (BRL 38227)
Route of Administration: Oral
Levcromakalim (0.1 uM) hyperpolarized the smooth muscle and decreased membrane resistance in the rat tail artery
Name Type Language
LEVCROMAKALIM DISODIUM PHOSPHATE
Preferred Name English
Foslevcromakalim sodium
Common Name English
LEVCROMAKALIM PHOSPHATE ESTER SODIUM SALT
Common Name English
(3S,4R)-3,4-DIHYDRO-2,2-DIMETHYL-4-(2-OXO-1-PYRROLIDINYL)-3-(PHOSPHONOOXY)-2H-1-BENZOPYRAN-6-CARBONITRILE, SODIUM SALT (1:2)
Systematic Name English
2H-1-BENZOPYRAN-6-CARBONITRILE, 3,4-DIHYDRO-2,2-DIMETHYL-4-(2-OXO-1-PYRROLIDINYL)-3-(PHOSPHONOOXY)-, SODIUM SALT (1:2), (3S,4R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
91826793
Created by admin on Wed Apr 02 10:33:16 GMT 2025 , Edited by admin on Wed Apr 02 10:33:16 GMT 2025
PRIMARY PUBCHEM
CAS
1802655-71-5
Created by admin on Wed Apr 02 10:33:16 GMT 2025 , Edited by admin on Wed Apr 02 10:33:16 GMT 2025
PRIMARY
FDA UNII
YBT5QW7T2V
Created by admin on Wed Apr 02 10:33:16 GMT 2025 , Edited by admin on Wed Apr 02 10:33:16 GMT 2025
PRIMARY