Carmoterol | TA-2005 | CHF-4226 | CAS#147568-66-9 | Adrenoreceptor Agonist

MedKoo Cat#: 524556 | Name: Carmoterol

Description:

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

Carmoterol, also known as TA-2005 and CHF-4226, is an ultra-long-acting β adrenoreceptor agonist. Preliminary studies indicated duration of its effect exceeding 24 hours after inhalation of 3 μg. The pharmacologic profile of this medication included the fact its potency in isolated guinea pig trachea is greater than that of formoterol and salmeterol. It is over 100 times more selective for bronchial muscle than myocardial tissue.

Chemical Structure

Carmoterol

CAS#147568-66-9 (free base)

Theoretical Analysis

MedKoo Cat#: 524556

Name: Carmoterol

CAS#: 147568-66-9 (free base)

Chemical Formula:

Exact Mass:

Molecular Weight:

Elemental Analysis:

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 #

147568-66-9 (free base) 137888-11-0 (HCl)

Synonym

Carmoterol ; CHF 4226; CHF-4226; CHF4226; TA-2005; TA 2005; TA2005.

IUPAC/Chemical Name

2(1H)-Quinolinone, 8-hydroxy-5-(1-hydroxy-2-((2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)-, (R-(R*,R*))-

InChi Key

IHOXNOQMRZISPV-YJYMSZOUSA-N

InChi Code

InChI=1S/C21H24N2O4/c1-13(11-14-3-5-15(27-2)6-4-14)22-12-19(25)16-7-9-18(24)21-17(16)8-10-20(26)23-21/h3-10,13,19,22,24-25H,11-12H2,1-2H3,(H,23,26)/t13-,19+/m1/s1

SMILES Code

O=C1NC2=C(C([C@@H](O)CN[C@H](C)CC3=CC=C(OC)C=C3)=CC=C2O)C=C1

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, not in water

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 0.00 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.

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: Montuschi P, Ciabattoni G. Bronchodilating drugs for chronic obstructive pulmonary disease: current status and future trends. J Med Chem. 2015 May 28;58(10):4131-64. doi: 10.1021/jm5013227. Epub 2015 Feb 9. PubMed PMID: 25587755. 2: Spina D. Current and novel bronchodilators in respiratory disease. Curr Opin Pulm Med. 2014 Jan;20(1):73-86. doi: 10.1097/MCP.0000000000000012. Review. PubMed PMID: 24247039. 3: Ridolo E, Montagni M, Olivieri E, Riario-Sforza GG, Incorvaia C. Role of indacaterol and the newer very long-acting β2-agonists in patients with stable COPD: a review. Int J Chron Obstruct Pulmon Dis. 2013;8:425-32. doi: 10.2147/COPD.S49179. Epub 2013 Sep 18. Review. PubMed PMID: 24082783; PubMed Central PMCID: PMC3785397. 4: Fuso L, Mores N, Valente S, Malerba M, Montuschi P. Long-acting beta-agonists and their association with inhaled corticosteroids in COPD. Curr Med Chem. 2013;20(12):1477-95. Review. PubMed PMID: 23409722. 5: Płusa T. [Novel controllers of airway obstruction in COPD patients]. Pol Merkur Lekarski. 2011 Jan;30(175):5-9. Polish. PubMed PMID: 21542237. 6: Cazzola M, Calzetta L, Matera MG. β(2) -adrenoceptor agonists: current and future direction. Br J Pharmacol. 2011 May;163(1):4-17. doi: 10.1111/j.1476-5381.2011.01216.x. Review. PubMed PMID: 21232045; PubMed Central PMCID: PMC3085864. 7: Warne T, Moukhametzianov R, Baker JG, Nehmé R, Edwards PC, Leslie AG, Schertler GF, Tate CG. The structural basis for agonist and partial agonist action on a β(1)-adrenergic receptor. Nature. 2011 Jan 13;469(7329):241-4. doi: 10.1038/nature09746. PubMed PMID: 21228877; PubMed Central PMCID: PMC3023143. 8: Patel S, Summerhill S, Stanley M, Perros-Huguet C, Trevethick MA. The reassertion profiles of long acting β2-adrenoceptor agonists in the guinea pig isolated trachea and human recombinant β2-adrenoceptor. Pulm Pharmacol Ther. 2011 Apr;24(2):247-55. doi: 10.1016/j.pupt.2010.11.004. Epub 2010 Dec 4. PubMed PMID: 21134482. 9: Tashkin DP, Fabbri LM. Long-acting beta-agonists in the management of chronic obstructive pulmonary disease: current and future agents. Respir Res. 2010 Oct 29;11:149. doi: 10.1186/1465-9921-11-149. Review. PubMed PMID: 21034447; PubMed Central PMCID: PMC2991288. 10: Ohar JA, Donohue JF. Mono- and combination therapy of long-acting bronchodilators and inhaled corticosteroids in advanced COPD. Semin Respir Crit Care Med. 2010 Jun;31(3):321-33. doi: 10.1055/s-0030-1254072. Epub 2010 May 21. Review. PubMed PMID: 20496301. 11: Cazzola M, Segreti A, Matera MG. Novel bronchodilators in asthma. Curr Opin Pulm Med. 2010 Jan;16(1):6-12. doi: 10.1097/MCP.0b013e32833303d2. Review. PubMed PMID: 19816179. 12: Capacchi S, Lipreri M, Rizzi A, Caló C, Peveri T, Catinella S. 1H NMR discrimination of CHF4226.01 diastereoisomers in DMSO-d6. Magn Reson Chem. 2009 Jul;47(7):551-61. doi: 10.1002/mrc.2427. PubMed PMID: 19373771. 13: Katritch V, Reynolds KA, Cherezov V, Hanson MA, Roth CB, Yeager M, Abagyan R. Analysis of full and partial agonists binding to beta2-adrenergic receptor suggests a role of transmembrane helix V in agonist-specific conformational changes. J Mol Recognit. 2009 Jul-Aug;22(4):307-18. doi: 10.1002/jmr.949. PubMed PMID: 19353579; PubMed Central PMCID: PMC2693451. 14: Tomillero A, Moral MA. Gateways to clinical trials. December 2008. Methods Find Exp Clin Pharmacol. 2008 Dec;30(10):761-82. PubMed PMID: 19271026. 15: Summerhill S, Stroud T, Nagendra R, Perros-Huguet C, Trevethick M. A cell-based assay to assess the persistence of action of agonists acting at recombinant human beta(2) adrenoceptors. J Pharmacol Toxicol Methods. 2008 Nov-Dec;58(3):189-97. doi: 10.1016/j.vascn.2008.06.003. Epub 2008 Jul 2. PubMed PMID: 18652905. 16: Cazzola M, Matera MG. Novel long-acting bronchodilators for COPD and asthma. Br J Pharmacol. 2008 Oct;155(3):291-9. doi: 10.1038/bjp.2008.284. Epub 2008 Jul 7. Review. PubMed PMID: 18604231; PubMed Central PMCID: PMC2567883. 17: De Backer JW, Vos WG, Devolder A, Verhulst SL, Germonpré P, Wuyts FL, Parizel PM, De Backer W. Computational fluid dynamics can detect changes in airway resistance in asthmatics after acute bronchodilation. J Biomech. 2008;41(1):106-13. Epub 2007 Aug 14. PubMed PMID: 17698073. 18: Matera MG, Cazzola M. ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD? Drugs. 2007;67(4):503-15. Review. PubMed PMID: 17352511. 19: Rossoni G, Manfredi B, Razzetti R, Civelli M, Berti F. Positive interaction of the novel beta2-agonist carmoterol and tiotropium bromide in the control of airway changes induced by different challenges in guinea-pigs. Pulm Pharmacol Ther. 2007;20(3):250-7. Epub 2006 Mar 14. PubMed PMID: 16533614. 20: Cazzola M, Matera MG, Lötvall J. Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. Review. PubMed PMID: 16022567.