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)

HIDE SMILES / InChI

Molecular Formula	C22H28N2O5S2
Molecular Weight	464.598
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Lack of correlation between exercise and sibenadet-induced changes in heart rate corrected measurement of the QT interval.	2007-03	17380588
Understanding the polymorphic behavior of sibenadet hydrochloride through detailed studies integrating structural and dynamical assessment.	2005-11	16200581
Mucociliary clearance in COPD can be increased by both a D2/beta2 and a standard beta2 agonists.	2005-02	15715181
Multivariate estimation of the relative dose potency.	2004-07-30	15236424
Suppression of histamine-induced tachypnoea in the rhesus monkey by sibenadet: no role for dopamine D2 receptors.	2004-01	15307823
Conclusion. Lessons from the novel D2 dopamine receptor, beta2-adrenoceptor agonist, Viozan: chronic obstructive pulmonary disease and drug development implications.	2003-01	12564613
Evaluating symptoms in chronic obstructive pulmonary disease: validation of the Breathlessness, Cough and Sputum Scale.	2003-01	12564612
Utilization of health care services by patients with chronic obstructive pulmonary disease.	2003-01	12564611
Long-term use of Viozan (sibenadet HCl) in patients with chronic obstructive pulmonary disease: results of a 1-year study.	2003-01	12564610
Symptoms are an important outcome in chronic obstructive pulmonary disease clinical trials: results of a 3-month comparative study using the Breathlessness, Cough and Sputum Scale (BCSS).	2003-01	12564609
The role of the novel D2/beta2-agonist, Viozan (sibenadet HCl), in the treatment of symptoms of chronic obstructive pulmonary disease: results of a large-scale clinical investigation.	2003-01	12564608
Early clinical investigation of Viozan (sibenadet HCl), a novel D2 dopamine receptor, beta2-adrenoceptor agonist for the treatment of chronic obstructive pulmonary disease symptoms.	2003-01	12564607
Dual dopamine D2 receptor and beta2-adrenoceptor agonists for the treatment of chronic obstructive pulmonary disease: the pre-clinical rationale.	2003-01	12564606
Introduction. The symposium that never occurred: pre-clinical and clinical development of sibenadet.	2003-01	12564605
Dynamic modelling of a challenge-escalation cross-over study of treatment of capsaicin-induced coughing.	2002-10-30	12369079
Inhibition by viozan of extravasation induced in rat trachea by capsaicin is mediated exclusively by beta 2-adrenoceptors.	2001-12	11770013

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:06:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:01 GMT 2025`
Record UNII	N32934RHGW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIBENADET

Official Name

English

sibenadet [INN]

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C48149