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D6942

Sigma-Aldrich

DK-AH 269

≥98% (HPLC), solid

Synonyme(s) :

cilobradine hydrochloride

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About This Item

Formule empirique (notation de Hill) :
C28H38N2O5 · HCl
Numéro CAS:
186097-54-1
Poids moléculaire :
519.07
Numéro MDL:
MFCD07776908
Code UNSPSC :
12352200
ID de substance PubChem :
24724467
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

solid

Couleur

white

Solubilité

H2O: ~20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

O=C1CC2=CC(OC)=C(OC)C=C2CCN1C[C@@H](CCC3)CN3CCC4=CC(OC)=C(OC)C=C4.[H]Cl

InChI

1S/C28H38N2O5.ClH/c1-32-24-8-7-20(14-25(24)33-2)9-12-29-11-5-6-21(18-29)19-30-13-10-22-15-26(34-3)27(35-4)16-23(22)17-28(30)31;/h7-8,14-16,21H,5-6,9-13,17-19H2,1-4H3;1H/t21-;/m0./s1

Clé InChI

MTAKUIYCCYKGJJ-BOXHHOBZSA-N

Application

DK-AH 269 has been used as a hyperpolarization-activated and cyclic nucleotide-gated channel (HCN) antagonist to study its effects on the inhibition of Ih in HCN-deficient hair cells of mice. It has also been used as an HCN blocker to study its effects on action potential firing in the suprachiasmatic nucleus (SCN) neurons.

Actions biochimiques/physiologiques

DK-AH 269 (Cilobradine) is an HCN Channel blocker; an open channel blocker of neuronal Ih and related cardiac If channels.
DK-AH 269 is a bradycardiac agent.

Caractéristiques et avantages

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 is featured on the Cyclic Nucleotide-Gated (CNG) and Hyperpolarization Activated Cyclic Nucleotide-Gated (HCN) Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
025K4609

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Consulter la Bibliothèque de documents

HCN channels expressed in the inner ear are necessary for normal balance function
Horwitz G C, et al.
The Journal of Neuroscience, 31(46), 16814-16825 (2011)
A Raes et al.
British journal of pharmacology, 125(4), 741-750 (1998-12-01)
1. The sinus node inhibitors UL FS 49 and DK-AH 269 reduce heart rate by slowing diastolic depolarization rate in the sino-atrial (SA) node, which might originate from the use-dependent blockade of a hyperpolarization-activated current If. A hyperpolarization-activated current Ih
Vivien Chevaleyre et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(14), 9538-9543 (2002-07-03)
Hyperpolarization-activated nonselective cation channels (Ih channels) play an important role in the control of membrane excitability and rhythmic neuronal activity. The functional relevance of presynaptic Ih channels in regulating synaptic function, however, is not well established. Recently, it has been
Effects of a bradycardic agent (DK-AH 269) on haemodynamics and oxygen consumption of isolated blood-perfused rabbit hearts
Granetzny A, et al.
Journal of Clinical and Basic Cardiology, 3(3), 191-196 (2000)
H C Pape
Neuroscience, 59(2), 363-373 (1994-03-01)
A class of pharmacologically active substances, known as "specific bradycardic agents", exerts a negative chronotropic influence on cardiac activity, which heavily relies upon a potent blockade of the hyperpolarization-activated cation current in Purkinje fibers. Since the cation conductance activated by
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