A Ca2+ channel activator
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(S)-(−)-BAY-K-8644

Item No. 19988

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-1,4-dihydro-2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-3-pyridinecarboxylic acid, methyl ester
CAS Number
98625-26-4
Molecular Formula
C16H15F3N2O4
Formula Weight
356.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2) (1:9): 0.1 mg/ml
λmax
236, 272, 404 nm
SMILES
O=C(OC)C1=C(C)NC(C)=C([N+]([O-])=O)[C@H]1C2=CC=CC=C2C(F)(F)F
InChi Code
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/t13-/m0/s1
InChi Key
ZFLWDHHVRRZMEI-ZDUSSCGKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $36

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    1 mg

    $68

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    5 mg

    $236

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    10 mg

    $322

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    Product Description

    (S)-(−)-BAY-K-8644 is an activator of voltage-sensitive L-type calcium channels.1,2 It demonstrates vasoconstrictive and positive inotropic effects in vivo as well as behavioral effects, including deficits to motor function.3,4 When combined with BIX01294 (Item No. 13124), (S)-(−)-BAY-K-8644 can enable reprogramming of mouse embryonic fibroblasts after transduction with Oct4/Klf4.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ravens, U., and Schöpper, H.P. Opposite cardiac actions of the enantiomers of Bay K 8644 at different membrane potentials in guinea-pig papillary muscles. Naunyn Schmiedebergs Arch. Pharmacol. 341(3), 232-239 (1990).

    2. Artigas, P., Ferreira, G., Reyes, N., et al. Effects of the enantiomers of BayK 8644 on the charge movement of L-type Ca channels in guinea-pig ventricular myocytes. J. Membr. Biol. 193(3), 215-227 (2003).

    3. Franckowiak, G., Bechem, M., Schramm, M., et al. The optical isomers of the 1,4-dihydropyridine Bay K 8644 show opposite effects on Ca channels. Eur. J. Pharmacol. 114(2), 223-226 (1985).

    4. O'Neill, S.K., and Bolger, G.T. Enantiomer selectivity and the development of tolerance to the behavioral effects of the calcium channel activator BAY K 8644. Brain Res. Bull. 21(6), 865-872 (1988).

    5. Shi, Y., Desponts, C., Do, J.T., et al. Induction of pluripotent stem cells from mouse embryonic fibroblasts by Oct4 and Klf4 with small-molecule compounds. Cell Stem Cell 3(5), 568-574 (2008).