71145-03-4 Usage
Description
(+/-)-BAY K 8644, also known as BAY K8644, is an L-type Ca2+-channel activator that exhibits positive inotropic and vasoconstrictive effects. It is a synthetic organic compound with the chemical formula C22H29NO4 and a molecular weight of 367.47 g/mol. As an active L-type, voltage-gated calcium channel agonist, it plays a crucial role in various physiological processes and has potential applications in different industries.
Uses
Used in Pharmaceutical Industry:
(+/-)-BAY K 8644 is used as a research tool and drug candidate for the development of cardiovascular medications. Its ability to activate L-type calcium channels helps in enhancing the contractility of heart muscles, making it a potential therapeutic agent for treating heart failure and other cardiovascular disorders.
Used in Research and Development:
(+/-)-BAY K 8644 is used as a research compound in the field of pharmacology and neuroscience. It aids in studying the role of L-type calcium channels in various physiological processes, such as neurotransmitter release, muscle contraction, and hormone secretion. This knowledge can contribute to the development of new drugs and therapies for various diseases and conditions.
Used in Toxicology Studies:
(+/-)-BAY K 8644 is used in toxicology studies to evaluate the safety and potential side effects of drugs and chemicals. Its ability to activate L-type calcium channels can help researchers understand the mechanisms of drug-induced toxicity and develop strategies to mitigate these effects.
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]
References
1) Schramm?et al. (1983)?Novel Dihydropyridines with positive inotropic action through activation of Ca2+ channels; Nature,?303?535
2) Yamamoto?et al. (1984)?Bay K8644 Differentiates between potential and receptor operated Ca2+ channels; Eur. J. Pharmacol.?102?555
3) Thomas?et al. (1985)?A dihydropyridine (Bay K 8644) that enhances calcium currents in guinea pig and calf myocardial cells. A new type of positive inotropic agent; Circ. Res.,?56?87
4) Shi?et al. (2009)?Induction of pluripotent stem cells from mouse embryonic fibroblasts by Oct4 and Klf4 with small molecule compounds; Cell Stem Cell,?3?568
Check Digit Verification of cas no
The CAS Registry Mumber 71145-03-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,1,4 and 5 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 71145-03:
(7*7)+(6*1)+(5*1)+(4*4)+(3*5)+(2*0)+(1*3)=94
94 % 10 = 4
So 71145-03-4 is a valid CAS Registry Number.
InChI:InChI=1/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/h4-7,12-13H,1-3H3/t12?,13-/m1/s1
71145-03-4Relevant articles and documents
Process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines
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, (2008/06/13)
A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.
Mixtures of optically active nitrodihydropyridines active on the circulatory system
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, (2008/06/13)
Pure enantiomers of 5-nitrodihydropyridine of the formula STR1 are mixed, wherein one of the enantiomers has a high vasodilative action and a low negative inotropic activity on heart muscle, the other enantiomer has a low vasoconstrictive action and a hig
Nitro-substituted 1,4-dihydropyridines, processes for _their production and their medicinal use
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, (2008/06/13)
The invention includes novel nitro-substituted 1,4-dihydropyridines useful because of their influence on the circulation. Also included in the invention are methods for the preparation of said novel nitro-substituted 1,4-dihydropyridines, compositions con
