(R)-(+)-BAY-K-8644 | CAS# 98791-67-4 | L-type channel blocker

MedKoo Cat#: 574576 | Name: (R)-(+)-BAY-K-8644

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(R)-(+)-BAY-K-8644 is an L-type channel blocker that has negative inotropic and vasodilatory effects. Intracerebroventricular administration of this enantiomer has no effect on motor function in mice, whereas (S)-(−)-BAY-K-8644 impairs rotarod and motor activity, an effect that is blocked by (R)-(+)-BAY-K-8644.

Chemical Structure

(R)-(+)-BAY-K-8644

CAS#98791-67-4 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 574576

Name: (R)-(+)-BAY-K-8644

CAS#: 98791-67-4 (R-isomer)

Chemical Formula: C15H13F3N2O4

Exact Mass: 342.0827

Molecular Weight: 342.27

Elemental Analysis: C, 52.64; H, 3.83; F, 16.65; N, 8.18; O, 18.70

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

71145-03-4 (racemate) 98791-67-4 (R-isomer)

Synonym

(R)-(+)-BAY-K-8644; BAYK 8644; BAYK8644; BAYK-8644; BAY K 8644; BAY K8644; BA YK-8644; NI 105; R 4407;

IUPAC/Chemical Name

(4R)-1,4-dihydro-2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-3-pyridinecarboxylic acid

InChi Key

QTKFDQYPMABWIR-GFCCVEGCSA-N

InChi Code

InChI=1S/C15H13F3N2O4/c1-7-11(14(21)22)12(13(20(23)24)8(2)19-7)9-5-3-4-6-10(9)15(16,17)18/h3-6,12,19H,1-2H3,(H,21,22)/t12-/m1/s1

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 342.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Tikhonov DB, Zhorov BS. Mechanisms of dihydropyridine agonists and antagonists in view of cryo-EM structures of calcium and sodium channels. J Gen Physiol. 2023 Nov 6;155(11):e202313418. doi: 10.1085/jgp.202313418. Epub 2023 Sep 20. PMID: 37728574; PMCID: PMC10510735. 2: Ji J, Kang J, Rampe D. L-type Ca2+ channel responses to bay k 8644 in stem cell-derived cardiomyocytes are unusually dependent on holding potential and charge carrier. Assay Drug Dev Technol. 2014 Aug;12(6):352-60. doi: 10.1089/adt.2014.596. PMID: 25147907; PMCID: PMC4142808. 3: Sidaway P, Teramoto N. L-type Ca2+ channel sparklets revealed by TIRF microscopy in mouse urinary bladder smooth muscle. PLoS One. 2014 Apr 3;9(4):e93803. doi: 10.1371/journal.pone.0093803. PMID: 24699670; PMCID: PMC3974850. 4: Zhu HL, Teramoto N. Antagonistic actions of S(-)-Bay K 8644 on cyclic nucleotide-induced inhibition of voltage-dependent Ba(2+) currents in guinea pig gastric antrum. Naunyn Schmiedebergs Arch Pharmacol. 2008 Dec;378(6):609-15. doi: 10.1007/s00210-008-0332-5. Epub 2008 Jul 23. PMID: 18648774. 5: Yamaguchi S, Zhorov BS, Yoshioka K, Nagao T, Ichijo H, Adachi-Akahane S. Key roles of Phe1112 and Ser1115 in the pore-forming IIIS5-S6 linker of L-type Ca2+ channel alpha1C subunit (CaV 1.2) in binding of dihydropyridines and action of Ca2+ channel agonists. Mol Pharmacol. 2003 Aug;64(2):235-48. doi: 10.1124/mol.64.2.235. PMID: 12869628. 6: Zhorov BS, Folkman EV, Ananthanarayanan VS. Homology model of dihydropyridine receptor: implications for L-type Ca(2+) channel modulation by agonists and antagonists. Arch Biochem Biophys. 2001 Sep 1;393(1):22-41. doi: 10.1006/abbi.2001.2484. PMID: 11516158. 7: Chesnoy-Marchais D, Cathala L. Modulation of glycine responses by dihydropyridines and verapamil in rat spinal neurons. Eur J Neurosci. 2001 Jun;13(12):2195-204. doi: 10.1046/j.0953-816x.2001.01599.x. PMID: 11454022. 8: Ko FN, Huang SY, Teng CM. Activation by high potassium of a novel voltage- operated Ca2+ channel in rat spleen. Br J Pharmacol. 1997 Feb;120(4):565-70. doi: 10.1038/sj.bjp.0700935. PMID: 9051291; PMCID: PMC1564497. 9: Pike CJ, Balázs R, Cotman CW. Attenuation of beta-amyloid neurotoxicity in vitro by potassium-induced depolarization. J Neurochem. 1996 Oct;67(4):1774-7. doi: 10.1046/j.1471-4159.1996.67041774.x. PMID: 8858966. 10: Zhorov BS, Ananthanarayanan VS. Structural model of a synthetic Ca2+ channel with bound Ca2+ ions and dihydropyridine ligand. Biophys J. 1996 Jan;70(1):22-37. doi: 10.1016/S0006-3495(96)79561-9. PMID: 8770184; PMCID: PMC1224906. 11: Robitaille R, Bourque MJ, Vandaele S. Localization of L-type Ca2+ channels at perisynaptic glial cells of the frog neuromuscular junction. J Neurosci. 1996 Jan;16(1):148-58. doi: 10.1523/JNEUROSCI.16-01-00148.1996. PMID: 8613781; PMCID: PMC6578703. 12: Smart D, Lambert DG. Desensitization of the mu-opioid activation of phospholipase C in SH-SY5Y cells: the role of protein kinases C and A and Ca(2+)-activated K+ currents. Br J Pharmacol. 1995 Nov;116(6):2655-60. doi: 10.1111/j.1476-5381.1995.tb17222.x. PMID: 8590985; PMCID: PMC1909131. 13: Usowicz MM, Gigg M, Jones LM, Cheung CW, Hartley SA. Allosteric interactions at L-type calcium channels between FPL 64176 and the enantiomers of the dihydropyridine Bay K 8644. J Pharmacol Exp Ther. 1995 Nov;275(2):638-45. PMID: 7473149. 14: Tiwari-Woodruff SK, Cox TC. Boar sperm plasma membrane Ca(2+)-selective channels in planar lipid bilayers. Am J Physiol. 1995 May;268(5 Pt 1):C1284-94. doi: 10.1152/ajpcell.1995.268.5.C1284. PMID: 7539216. 15: O'Neill SK, McKay DW, Campbell N, Triggle CR, Crowley M, Bolger GT. Comparative behavioral, neurochemical and pharmacological activities of dihydropyridine calcium channel activating drugs. J Pharmacol Exp Ther. 1990 Jun;253(3):905-12. PMID: 1694243. 16: Hashim MA, Bolger GT, Bieger D. Modulation of solitarial deglutitive N-methyl-D-aspartate receptors by dihydropyridines. Neuropharmacology. 1989 Sep;28(9):923-9. doi: 10.1016/0028-3908(89)90191-3. PMID: 2478924. 17: Wei XY, Rutledge A, Zhong Q, Ferrante J, Triggle DJ. Ca2+ channels in chick neural retina cells characterized by 1,4-dihydropyridine antagonists and activators. Can J Physiol Pharmacol. 1989 May;67(5):506-14. doi: 10.1139/y89-080. PMID: 2548693. 18: Wei XY, Rutledge A, Triggle DJ. Voltage-dependent binding of 1,4-dihydropyridine Ca2+ channel antagonists and activators in cultured neonatal rat ventricular myocytes. Mol Pharmacol. 1989 Apr;35(4):541-52. PMID: 2539561. 19: O'Neill SK, Bolger GT. Enantiomer selectivity and the development of tolerance to the behavioral effects of the calcium channel activator BAY K 8644. Brain Res Bull. 1988 Dec;21(6):865-72. doi: 10.1016/0361-9230(88)90019-6. PMID: 2465070. 20: Wei XY, Luchowski EM, Rutledge A, Su CM, Triggle DJ. Pharmacologic and radioligand binding analysis of the actions of 1,4-dihydropyridine activator- antagonist pairs in smooth muscle. J Pharmacol Exp Ther. 1986 Oct;239(1):144-53. PMID: 2428971.