CILOBRADINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H38N2O5
Molecular Weight	482.6117
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CCN2CCC[C@H](CN3CCC4=CC(OC)=C(OC)C=C4CC3=O)C2)C=C1OC

InChI

InChIKey=OBUFMJDDZTXJPY-NRFANRHFSA-N

InChI=1S/C28H38N2O5/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/t21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H38N2O5
Molecular Weight	482.6117
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17692005 | https://www.ncbi.nlm.nih.gov/pubmed/23229858 | https://www.ncbi.nlm.nih.gov/pubmed/17587152

Cilobradine is an Hyperpolarization-activated cyclic nucleotide-gated (HCN) channel blocker patented by a pharmaceutical company Boehringer Ingelheim G.m.b.H. for sinus tachycardia treatment. In clinical trials Cilobradine decrease Heart rate. Chronically increased heart rate (HR) is a risk factor for mortality and morbidity with adverse consequences on vascular function, atherogenesis, myocardial ischemia, myocardial energetics and left the ventricular function. Heart rate response was found to be concentration-dependent and appeared with a significant delay with respect to the time course of cilobradine in plasma.

Originator

Approval Year

PubMed

Title	Date	PubMed
Bradycardic and proarrhythmic properties of sinus node inhibitors.	2006 Apr	16387796

Patents

Sample Use Guides

In Vivo Use Guide

orally once daily over 2 weeks at 0.25–5 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:51:48 GMT 2023` Edited by `admin` on `Sat Dec 16 17:51:48 GMT 2023`
Record UNII	5O1LL04GJ3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CILOBRADINE

Official Name

English

(+)-(S)-3-((1-(3,4-DIMETHOXYPHENETHYL)-3-PIPERIDYL)METHYL)-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE

Systematic Name

English

2H-3-BENZAZEPIN-2-ONE, 3-(((3S)-1-(2-(3,4-DIMETHOXYPHENYL)ETHYL)-3-PIPERIDINYL)METHYL)-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-

Systematic Name

English

2H-3-BENZAZEPIN-2-ONE, 3-((1-(2-(3,4-DIMETHOXYPHENYL)ETHYL)-3-PIPERIDINYL)METHYL)-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-, (S)-

Common Name

English

cilobradine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793