Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H28N2O5S2.ClH |
Molecular Weight | 501.059 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.OC1=C2NC(=O)SC2=C(CCNCCS(=O)(=O)CCCOCCC3=CC=CC=C3)C=C1
InChI
InChIKey=YXOKBHUPEBNZOG-UHFFFAOYSA-N
InChI=1S/C22H28N2O5S2.ClH/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);1H
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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
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 |
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Long-term use of Viozan (sibenadet HCl) in patients with chronic obstructive pulmonary disease: results of a 1-year study. | 2003 Jan |
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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 Jan |
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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 Jan |
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Introduction. The symposium that never occurred: pre-clinical and clinical development of sibenadet. | 2003 Jan |
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Suppression of histamine-induced tachypnoea in the rhesus monkey by sibenadet: no role for dopamine D2 receptors. | 2004 Jan |
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Multivariate estimation of the relative dose potency. | 2004 Jul 30 |
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Mucociliary clearance in COPD can be increased by both a D2/beta2 and a standard beta2 agonists. | 2005 Feb |
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Understanding the polymorphic behavior of sibenadet hydrochloride through detailed studies integrating structural and dynamical assessment. | 2005 Nov |
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Lack of correlation between exercise and sibenadet-induced changes in heart rate corrected measurement of the QT interval. | 2007 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12564607
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9836607
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
Edited
Fri Dec 15 15:51:55 GMT 2023
by
admin
on
Fri Dec 15 15:51:55 GMT 2023
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Record UNII |
659OIV373Y
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Record Status |
Validated (UNII)
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Record Version |
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C66884
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NCI_THESAURUS |
C48149
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183811
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C76551
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DTXSID90165551
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659OIV373Y
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CHEMBL82663
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154189-24-9
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100000175528
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NN-46
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