A class III antiarrhythmic agent
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Nifekalant (hydrochloride)

Item No. 20997

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[[2-[(2-hydroxyethyl)[3-(4-nitrophenyl)propyl]amino]ethyl]amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione, monohydrochloride
CAS Number
130656-51-8
Synonyms
  • MS-551
Molecular Formula
C19H27N5O5 • HCl
Formula Weight
441.9
Purity
≥98%
Formulation
A crystalline solid
λmax
267 nm
SMILES
OCCN(CCNC1=CC(N(C)C(N1C)=O)=O)CCCC2=CC=C([N+]([O-])=O)C=C2.Cl
InChi Code
InChI=1S/C19H27N5O5.ClH/c1-21-17(14-18(26)22(2)19(21)27)20-9-11-23(12-13-25)10-3-4-15-5-7-16(8-6-15)24(28)29;/h5-8,14,20,25H,3-4,9-13H2,1-2H3;1H
InChi Key
YPVGGQKNWAKOPX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $110

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    10 mg

    $143

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    25 mg

    $268

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    Product Description

    Nifekalant is a class III antiarrhythmic agent.1 It inhibits the rapidly activating delayed rectifier potassium channel (IKr; IC50 = 10 µM) and prolongs cardiac action potential duration (APD) in isolated dog Purkinje fibers when used at concentrations of 1 and 3 µg/ml.1,2 Nifekalant (3 mg/kg) inhibits arrhythmias induced by programmed electrical stimulation (PES) in dogs post myocardial infarction.3 It increases atrial and ventricular effective refractory periods (ERPs) in anesthetized dogs.4 Nifekalant also inhibits human multidrug and toxin extrusion (MATE) transporter 1 (MATE1; IC50 = 6.5 µM).5 Formulations containing nifekalant have been used in the treatment of arrhythmias and ventricular tachycardia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Katakami, T., Yokoyama, T., Miyamoto, M., et al. Synthesis and pharmacological studies of N-substituted 6-[(2-aminoethyl)amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinediones, novel class III antiarrhythmic agents. J. Med. Chem. 35(18), 3325-3330 (1992).

    2. Du, L.P., Tsai, K.C., Li, M.Y., et al. The pharmacophore hypotheses of IKr potassium channel blockers: Novel class III antiarrhythmic agents. Bioorg. Med. Chem. Lett. 14(18), 4771-4777 (2004).

    3. Kamiya, J., Ishii, M., and Katakami, T. Antiarrhythmic effects of MS-551, a new class III antiarrhythmic agent, on canine models of ventricular arrhythmia. Jpn. J. Pharmacol. 58(2), 107-115 (1992).

    4. Kamiya, J., Ishii, M., Yoshihara, K., et al. MS-551: Pharmacological profile of a novel class III antiarrhythmic agent. Drug Develop. Res. 30(1), 37-44 (1993).

    5. Wittwer, M.B., Zur, A.A., Khuri, N., et al. Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J. Med. Chem. 56(3), 781-795 (2013).