Skip to Content
Merck
All Photos(1)

Key Documents

Z0127

Sigma-Aldrich

Zatebradine hydrochloride

≥98% (HPLC), powder

Synonym(s):

7,8-Dimethoxy-3-[3-[-N-[2-(3,4 dimethoxyphenyl)ethyl]-N-methylamino]propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one hydrochloride, UL-FS49

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C26H37ClN2O5
CAS Number:
Molecular Weight:
493.04
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

H2O: >10 mg/mL

originator

Boehringer Ingelheim

storage temp.

2-8°C

SMILES string

Cl[H].COc1ccc(CCN(C)CCCN2CCc3cc(OC)c(OC)cc3CC2=O)cc1OC

InChI

1S/C26H36N2O5.ClH/c1-27(13-9-19-7-8-22(30-2)23(15-19)31-3)11-6-12-28-14-10-20-16-24(32-4)25(33-5)17-21(20)18-26(28)29;/h7-8,15-17H,6,9-14,18H2,1-5H3;1H

InChI key

ZRNKXJHEQKMWCH-UHFFFAOYSA-N

Application

Zatebradine hydrochloride has been used:
  • as an If blocker to study its effects on cardiomyocyte clusters (CMCs)
  • as a hyperpolarization-activated and cyclic nucleotide-gated (HCN) channel inhibitor to study its effects on viability of degenerating rod or cone photoreceptors in mice
  • as a bradycardiac agent to study its effects on tachycardia and elevated temperature in fish

Biochem/physiol Actions

Zatebradine is a bradycardiac agent.
HCN channel blocker: blocker of neuronal Ih, related cardiac If channels and ATP-sensitive Kir channels.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Christopher M Wilson et al.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology, 164(1), 258-263 (2012-09-27)
Pharmacological ion-channel blockers were used to investigate the spontaneous heart rates in Pacific hagfish, Eptatretus stoutii. Zatebradine, a hyperpolarization-activated cyclic nucleotide-gated (HCN) channel blocker, vastly reduced atrial and ventricular contraction rates in a similar concentration-dependent manner, indicating a major role
Effects of zatebradine and propranolol on canine ischemia and reperfusion-induced arrhythmias
Naito H, et al.
European Journal of Pharmacology, 388(2), 171-176 (2000)
Hiroko Izumi-Nakaseko et al.
Journal of pharmacological sciences, 135(1), 44-50 (2017-09-21)
Human induced pluripotent stem cell-derived cardiomyocytes (hiPSC-CMs) have been used in many studies to assess proarrhythmic risks of chemical compounds. In those studies, field potential durations (FPD) of hiPSC-CMs have been corrected by clinically used Fridericia's and/or Bazett's formulae, however
Cardiomyocyte clusters derived from human embryonic stem cells share similarities with human heart tissue
Asp J, et al.
Journal of Molecular Cell Biology, 2(5), 276-283 (2010)
William Joyce et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 188(3), 481-490 (2017-10-27)
The amount of blood pumped by the heart (cardiac output) must be matched to the amount of blood returning to the heart (venous return), but the factors determining cardiac filling are sparsely understood in ectothermic vertebrates. Stroke volume is affected

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service