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MedKoo Cat#: 327000 | Name: Sibenadet HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sibenadet, also known as AR-C-68397AA; FPL-68397; ARC-68397AA, is a D2/beta2-agonist and is potential useful for the treatment of symptoms of chronic obstructive pulmonary disease. (last updated: 10/13/2016)

Chemical Structure

Sibenadet HCl
Sibenadet HCl
CAS#154189-24-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 327000

Name: Sibenadet HCl

CAS#: 154189-24-9 (HCl)

Chemical Formula: C22H29ClN2O5S2

Exact Mass:

Molecular Weight: 501.05

Elemental Analysis: C, 52.74; H, 5.83; Cl, 7.08; N, 5.59; O, 15.97; S, 12.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
154189-40-9 (free base) 154189-24-9 (HCl)
Synonym
Sibenadet Hydrochloride; AR-C-68397AA; FPL-68397; ARC-68397AA; Viozan.
IUPAC/Chemical Name
4-Hydroxy-7-(2-(2-(3-phenylethoxy-propane-1-sulfonyl)-ethylamino)ethyl)-3H-benzothiazol-2-one hydrochloride.
InChi Key
YXOKBHUPEBNZOG-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1SC2=C(CCNCCS(=O)(CCCOCCC3=CC=CC=C3)=O)C=CC(O)=C2N1.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# 154189-40-9 (Sibenadet) 154189-24-9 (Sibenadet Hydrochloride)

Preparing Stock Solutions

The following data is based on the product molecular weight 501.05 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bradley JP, Pickard CJ, Burley JC, Martin DR, Hughes LP, Cosgrove SD, Brown SP. Probing intermolecular hydrogen bonding in sibenadet hydrochloride polymorphs by high-resolution (1) H double-quantum solid-state NMR spectroscopy. J Pharm Sci. 2012 May;101(5):1821-30. doi: 10.1002/jps.23078. Epub 2012 Feb 22. PubMed PMID: 22359321. 2: Alcaraz L, Bailey A, Cadogan E, Connolly S, Jewell R, Jordan S, Kindon N, Lister A, Lawson M, Mullen A, Dainty I, Nicholls D, Paine S, Pairaudeau G, Stocks MJ, Thorne P, Young A. From libraries to candidate: the discovery of new ultra long-acting dibasic β₂-adrenoceptor agonists. Bioorg Med Chem Lett. 2012 Jan 1;22(1):689-95. doi: 10.1016/j.bmcl.2011.10.049. Epub 2011 Oct 20. PubMed PMID: 22079756. 3: Connolly S, Alcaraz L, Bailey A, Cadogan E, Christie J, Cook AR, Fisher AJ, Hill S, Humphries A, Ingall AH, Kane Z, Paine S, Pairaudeau G, Stocks MJ, Young A. Design-driven LO: the discovery of new ultra long acting dibasic β2-adrenoceptor agonists. Bioorg Med Chem Lett. 2011 Aug 1;21(15):4612-6. doi: 10.1016/j.bmcl.2011.05.097. Epub 2011 Jun 13. PubMed PMID: 21723724. 4: Newbold P, Sanders N, Reele SB. Lack of correlation between exercise and sibenadet-induced changes in heart rate corrected measurement of the QT interval. Br J Clin Pharmacol. 2007 Mar;63(3):279-87. Epub 2006 Sep 12. PubMed PMID: 17380588; PubMed Central PMCID: PMC2000729. 5: Cosgrove SD, Steele G, Austin TK, Plumb AP, Stensland B, Ferrari E, Roberts KJ. Understanding the polymorphic behavior of sibenadet hydrochloride through detailed studies integrating structural and dynamical assessment. J Pharm Sci. 2005 Nov;94(11):2403-15. PubMed PMID: 16200581. 6: Hasani A, Toms N, Agnew JE, Lloyd J, Dilworth JP. Mucociliary clearance in COPD can be increased by both a D2/beta2 and a standard beta2 agonists. Respir Med. 2005 Feb;99(2):145-51. PubMed PMID: 15715181. 7: Fozard JR, Buescher H, Farr DC, Mazzoni L. Suppression of histamine-induced tachypnoea in the rhesus monkey by sibenadet: no role for dopamine D2 receptors. Auton Autacoid Pharmacol. 2004 Jan;24(1):9-16. PubMed PMID: 15307823. 8: Källén A. Multivariate estimation of the relative dose potency. Stat Med. 2004 Jul 30;23(14):2187-93. PubMed PMID: 15236424. 9: Calverley P, Keating ET, Goldman M, Casty F. Conclusion. Lessons from the novel D2 dopamine receptor, beta2-adrenoceptor agonist, Viozan: chronic obstructive pulmonary disease and drug development implications. Respir Med. 2003 Jan;97 Suppl A:S71-4. PubMed PMID: 12564613. 10: Leidy NK, Schmier JK, Jones MK, Lloyd J, Rocchiccioli K. Evaluating symptoms in chronic obstructive pulmonary disease: validation of the Breathlessness, Cough and Sputum Scale. Respir Med. 2003 Jan;97 Suppl A:S59-70. PubMed PMID: 12564612. 11: O'Brien JA, Ward AJ, Jones MK, McMillan C, Lordan N. Utilization of health care services by patients with chronic obstructive pulmonary disease. Respir Med. 2003 Jan;97 Suppl A:S53-8. PubMed PMID: 12564611. 12: Hiller FC, Alderfer V, Goldman M. Long-term use of Viozan (sibenadet HCl) in patients with chronic obstructive pulmonary disease: results of a 1-year study. Respir Med. 2003 Jan;97 Suppl A:S45-52. PubMed PMID: 12564610. 13: Celli B, Halpin D, Hepburn R, Byrne N, Keating ET, Goldman M. 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). Respir Med. 2003 Jan;97 Suppl A:S35-43. PubMed PMID: 12564609. 14: Laursen LC, Lindqvist A, Hepburn T, Lloyd J, Perrett J, Sanders N, Rocchiccioli K. 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. Respir Med. 2003 Jan;97 Suppl A:S23-33. PubMed PMID: 12564608. 15: Ind PW, Laitinen L, Laursen L, Wenzel S, Wouters E, Deamer L, Nystrom P. Early clinical investigation of Viozan (sibenadet HCl), a novel D2 dopamine receptor, beta2-adrenoceptor agonist for the treatment of chronic obstructive pulmonary disease symptoms. Respir Med. 2003 Jan;97 Suppl A:S9-21. PubMed PMID: 12564607. 16: Dougall IG, Young A, Ince F, Jackson DM. Dual dopamine D2 receptor and beta2-adrenoceptor agonists for the treatment of chronic obstructive pulmonary disease: the pre-clinical rationale. Respir Med. 2003 Jan;97 Suppl A:S3-7. PubMed PMID: 12564606. 17: Rennard SI. Introduction. The symposium that never occurred: pre-clinical and clinical development of sibenadet. Respir Med. 2003 Jan;97 Suppl A:S1-2. PubMed PMID: 12564605. 18: Lindsey JK, Stevens JW, Jones B, Jackson D. Dynamic modelling of a challenge-escalation cross-over study of treatment of capsaicin-induced coughing. Stat Med. 2002 Oct 30;21(20):3023-33. PubMed PMID: 12369079. 19: Fozard JR, Baur F, Wolber C, Collingwood SP. Inhibition by viozan of extravasation induced in rat trachea by capsaicin is mediated exclusively by beta 2-adrenoceptors. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):570-2. PubMed PMID: 11770013. 20: Willson VJ, Lockley WJ, Mather A, Singh J, Gilbert CM, Bayliss MA, Wilkinson D. A time-resolved fluorescence immunoassay for the determination of a novel respiratory therapeutic agent, AR-C68397XX (Viozan) in human plasma. J Pharm Biomed Anal. 2000 Nov;23(6):947-54. PubMed PMID: 11095295.