(+/-)-BAY K 8644 Chemical Properties

Melting point:

166 °C

Boiling point:

429.2±45.0 °C(Predicted)

Density 

1.3548 (estimate)

RTECS 

US5655000

storage temp. 

2-8°C

solubility 

DMSO: 184 mg/mL

pka

-3.43±0.70(Predicted)

form 

Yellow solid.

color 

Yellow

Water Solubility 

Soluble in DMSO at 20mg/ml. Also soluble in methanol or ethanol at 60mg/ml. Insoluble in water

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C16H15F3N2O4/c1-8-12(15(22)25-3)13(14(21(23)24)9(2)20-8)10-6-4-5-7-11(10)16(17,18)19/h4-7,13,20H,1-3H3

InChIKey

ZFLWDHHVRRZMEI-UHFFFAOYSA-N

SMILES

C1(C)NC(C)=C([N+]([O-])=O)C(C2=CC=CC=C2C(F)(F)F)C=1C(OC)=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(+/-)-BAY K 8644 Usage And Synthesis

Description

BAY K8644 (71145-03-4) is an L-type Ca2+-channel activator with positive inotropic and vasoconstrictive effects.

Chemical Properties

yellow powder

Uses

An active L-type, voltage-gated calcium channel agonist

Definition

ChEBI: Methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate is a pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6. It is a dihydropyridine, a methyl ester, a C-nitro compound and a member of (trifluoromethyl)benzenes.

Biological Activity

L-type Ca 2+ -channel activator (EC 50 = 17.3 nM). Has positive inotropic, vasoconstrictive and behavioral effects in vivo . Separate enantiomers also available ((4R)-1,4-Dihydro-2,6-dimethyl-5-nitro-4-[2-trifluoromet hyl)phenyl]-3-pyridinecarboxylic acid methyl ester and (4S)-1,4-Dihydro-2,6-dimethyl-5-nitro-4-[2-trifluoromet hyl)phenyl]-3-pyridinecarboxylic acid methyl ester).

Biochem/physiol Actions

(±)-Bay K8644 is a 1,4-dihydropyridine (DHP) derivative and an agonist for L-type Ca2+ channels. However, it′s enantiomers (-)-BAY k8644 and (+)-BAY k8644 have opposing functionality with respect to Ca2+ channels as high-potency agonist and low-potency antagonist, respectively. (±)-Bay K8644 increases influx of Ca2+ specifically at voltage-gated calcium channels. It constricts blood vessels and heart contraction.

in vitro

it was demonstrated that bay k 8644 prolonged the mean ca2+ channel opening time in heart myocytes and neurones of spinal ganglia. an experiment using rat heart ventricles demonstrated that bay k 8644, at the final concentration of approximately 1 pm, had strong positive inotropic effect when added to the perfusion fluid. moreover, the addition of bay k 8644 to the chronic ethanol treatment significantly reduced the electrophysiological signs of withdrawal in the isolated hippocampal slices. [2, 3]

in vivo

study in mice demonstrated that bay k 8644 significantly ameliorated the ethanol withdrawal syndrome. when experimental animals were administered with an acute injection of bay k 8644, the convulsive behavior of mice could be monitored to increase for 2 hours. in addition, bay k 8644 was also reported to ameliorate hypotension in endotoxin-shocked rats. it could lead to a 37% decrease in heart rate of endotoxin-treated rats and 39% decrease in control rats in a dose-dependent manner. [3,4]

storage

+4°C

References

[1] M. SCHRAMM. Novel dihydropyridines with positive inotropic action through activation of Ca2+ channels[J]. Nature, 1983, 303 5917: 535-537. DOI:10.1038/303535a0
[2] HIROMICHI YAMAMOTO  Cornelis V B  Ok Hwang. Bay K8644 differentiates between potential and receptor operated Ca2+ channels[J]. European journal of pharmacology, 1984, 102 3: Pages 555-557. DOI:10.1016/0014-2999(84)90581-8
[3] G THOMAS  C J C  M Chung. A dihydropyridine (Bay k 8644) that enhances calcium currents in guinea pig and calf myocardial cells. A new type of positive inotropic agent.[J]. Circulation research, 1985, 56 1: 87-96. DOI:10.1161/01.res.56.1.87
[4] Induction of pluripotent stem cells from mouse embryonic fibroblasts by Oct4 and Klf4 with small molecule compounds

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