94470-67-4

Basic information

• Product Name: CROMAKALIM
• Synonyms: AKOS 91890;(+/-)-CROMAKALIM;CROMAKALIM;TRANS-3,4-DIHYDRO-3-HYDROXY-2,2-DIMETHYL-4-(2-OXO-1-PYRROLIDINYL)-2H-1-BENZOPYRAN-6-CARBONITRILE;(+/-)-TRANS-6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-4-(2-OXOPYRROLIDIN-1-YL)-2H-1-BENZOPYRAN-3-OL;[+/-]-TRANS-6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-4-[2-OXOPYRROLIDIN-1-YL]-2H-1-BENZOPYRAN-3-OL;Cromakalim=([+/-]-trans-6-Cyano-3,4-dihydro-2,2-;BRL-34915
• CAS NO: 94470-67-4
• Molecular Formula: C₁₆H₁₈N₂O₃
• Molecular Weight: 286.33
• Product Categories: All Inhibitors;Inhibitors
• Mol File: 94470-67-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 242-244°C
• Boiling Point: 482.3°Cat760mmHg
• Flash Point: 245.5°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 4.09E-10mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• CAS DataBase Reference: CROMAKALIM(CAS DataBase Reference)
• NIST Chemistry Reference: CROMAKALIM(94470-67-4)
• EPA Substance Registry System: CROMAKALIM(94470-67-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 94470-67-4(Hazardous Substances Data)

Usage

Description

(±)-Cromakalim is a prototypical activator of the ATP-sensitive potassium channel, SUR2-Kir6, that displays anti-ischemic (EC25 = 8.9 μM) and cardioprotective (IC50 = 0.03 μM) effects in rat hearts. (±)-Cromakalim has also been shown to relax bladder smooth muscle in vitro. It has been used to investigate potassium channel biology and as a scaffold to develop increasingly selective K+ channel openers with clinical relevance.

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 94470-67-4 differently. You can refer to the following data:
1. Cromakalim causes vasodilation by activation of potassim channels
2. 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.

Biological Activity

Prototypical K ATP channel opener. Relaxes rabbit isolated portal vein with an IC 50 value of 21 nM . Potent, orally active and hypotensive in vivo .

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.

References

1) Sanguinetti?et al. (1988),?BRL 34915 (cromakalim) activates ATP-sensitive K+ current in cardiac muscle; Proc. Natl. Acad. Sci. USA,?85?8360 2) Wu?et al.?(2011),?Reopening of ATP-sensitive potassium channels reduces neuropathic pain and regulates astroglial gap junctions in the rat spinal cord; Pain,?152?2605 3) Roy Chowdhury?et al.?(2017),?ATP sensitive potassium channel openers: A new class of ocular hypotensive agents; Exp. Eye Res.,?158?85 4) Cao?et al.?(2016),?Opening of the Adenosine Triphosphate-sensitive Potassium Channel Attenuates Morphine Tolerance by Inhibiting JNK and Astrocyte Activation in the Spinal Cord; Clin. J. Pain,?32?617

InChI:InChI=1/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

Upstream product

• 616-45-5 2-pyrrolidinon 
• 114865-21-3 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-bromo-4-hydroxy-2H-1-benzopyran 
• 65018-90-8 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 

Downstream Products

• 103774-92-1 cis-6-cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-2H-benzopyran-3-ol 
• 94535-51-0 3-Hydroxy-2,2-dimethyl-4-(2-oxo-pyrrolidin-1-yl)-chroman-6-carbonitrile 
• 94535-50-9 Levcromakalim 
• 94535-51-0 cromakalim 

Relevant articles and documents

4-(2-hydroxy-1-pyrrolidinyl and 1-piperidinyl)-2H-benzo[b]-pyran-3-ol derivatives

Compounds of formula (I): STR1 wherein: either one of R1 and R2 is hydrogen and the other is selected from the class of C1-6 alkylcarbonyl, benzoyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyloxy, C1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C1-6 alkylsulphinyl, C1-6 alkylsulphonyl, C1-6 alkoxysulphinyl, C1-6 alkoxysulphonyl, C1-6 alkylcarbonylamino, C1-6 alkoxycarbonylamino, C1-6 alkyl-thiocarbonyl, C1-6 alkoxy-thiocarbonyl, C1-6 alkyl-thiocarbonyloxy, C1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C1-6 alkyl groups, or C1-6 alkylsulphinylamino, C1-6 alkylsulphonylamino C1-6 alkoxysulphinylamino or C1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C1-6 alkylcarbonyl, nitro or cyano, or --C(C1-6 alkyl)NOH or --C(C1-6 alkyl)NNH2, or one of R1 and R2 is nitro, cyano or C1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C1-6 alkyl or by C2-7 alkanoyl; one of R3 and R4 is hydrogen or C1-4 alkyl and the other is C1-4 alkyl or R3 and R4 together are C2-5 polymethylene having anti-hypertensive activity.

Synthesis and antihypertensive activity of 4-(cyclic amido)-2H-1-benzopyrans

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