SIBENADET

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H28N2O5S2
Molecular Weight	464.598
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C2NC(=O)SC2=C(CCNCCS(=O)(=O)CCCOCCC3=CC=CC=C3)C=C1

InChI

InChIKey=DBCKRBGYGMVSTI-UHFFFAOYSA-N

InChI=1S/C22H28N2O5S2/c25-19-8-7-18(21-20(19)24-22(26)30-21)9-11-23-12-16-31(27,28)15-4-13-29-14-10-17-5-2-1-3-6-17/h1-3,5-8,23,25H,4,9-16H2,(H,24,26)

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Description
Sources: https://adisinsight.springer.com/drugs/800009719 | https://www.ncbi.nlm.nih.gov/pubmed/12564607

AstraZeneca R&D Charnwood (formerly Astra Charnwood, a subsidiary of AstraZeneca) was developing sibenadet (Viozan, AR-C68397AA) for the potential treatment of chronic obstructive pulmonary disease and asthma. Sibenadet is a dual D2 dopamine receptor, beta2-adrenoceptor agonist that combines bronchodilator activity with the sensory afferent modulating effects associated with D2-receptor agonism. Development of sibenadet has been discontinued due to disappointing efficacy findings.

Originator

Approval Year

PubMed

Title	Date	PubMed
Conclusion. Lessons from the novel D2 dopamine receptor, beta2-adrenoceptor agonist, Viozan: chronic obstructive pulmonary disease and drug development implications.	2003 Jan	12564613
Understanding the polymorphic behavior of sibenadet hydrochloride through detailed studies integrating structural and dynamical assessment.	2005 Nov	16200581
Lack of correlation between exercise and sibenadet-induced changes in heart rate corrected measurement of the QT interval.	2007 Mar	17380588

Patents

Sample Use Guides

In Vivo Use Guide

701 patients were randomized to one of three sibenadet dose groups (400, 600 or 1000 ug ex valve), salbutamol 200 ug, ipratropium bromide (IB) 40 ug or placebo, all three times daily via pressurized metered dose inhaler (pMDI) for 4 weeks. Once the results of Study 1 had been evaluated, a dose-ranging, study (Study 2) involving 872 patients randomized to receive sibenadet (45, 270, or 495 ug ex actuator), or placebo all three times daily via pMDI, for 6 weeks commenced.

Route of Administration: Respiratory

In Vitro Use Guide

Sibenadet is a weak R1-adrenoceptor agonist (R1(REA): p[A]50 6.08, IA 0.08). It is a dual D2-receptor agonist (D2(REA): p[A]50 8.94, IA 0.90; essentially a full agonist at the D2-receptor) and beta2-adrenoceptor partial agonist (beta2(GPT): p[A]50 7.95

Name

Type

Language

SIBENADET

Official Name

English

4-HYDROXY-7-(2-((2-((3-(2-PHENYLETHOXY)PROPYL)SULFONYL)ETHYL)AMINO)ETHYL)-1,3-BENZOTHIAZOL-2(3H)-ONE

Systematic Name

English

2(3H)-BENZOTHIAZOLONE, 4-HYDROXY-7-(2-((2-((3-(2-PHENYLETHOXY)PROPYL)SULFONYL)ETHYL)AMINO)ETHYL)-

Systematic Name

English

sibenadet [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149