Batefenterol
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MedKoo CAT#: 319652

CAS#: 743461-65-6 (free base)

Description: Batefenterol, also known as GSK961081 and TD-5959, is a Muscarinic Antagonist and β2-Agonist possessing both muscarinic antagonist (MA) and β2-adrenoceptor agonist (BA) properties (MABA). GSK-961081 displayed high affinity for hM2 (Ki = 1.4 nM), hM3 muscarinic receptors (Ki = 1.3 nM) and hβ2-adrenoceptors (Ki = 3.7 nM). GSK-961081 behaved as a potent hβ2-adrenoceptor agonist (EC50 = 0.29 nM for stimulation of cAMP levels) with 440- and 320-fold functional selectivity over hβ1- and hβ3-adrenoceptors, respectively.


Price and Availability

Size
Price

50mg
USD 650
500mg
USD 2650
5g
USD 8950
Size
Price

100mg
USD 950
1g
USD 3450
Size
Price

200mg
USD 1650
2g
USD 5450

Batefenterol, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 800mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319652
Name: Batefenterol
CAS#: 743461-65-6 (free base)
Chemical Formula: C40H42ClN5O7
Exact Mass: 739.2773
Molecular Weight: 740.254
Elemental Analysis: C, 64.90; H, 5.72; Cl, 4.79; N, 9.46; O, 15.13


Related CAS #: 945905-37-3(succinate)   743461-65-6 (free base)    

Synonym: GSK961081; GSK-961081; GSK 961081; TD-5959; TD 5959; TD5959; Batefenterol

IUPAC/Chemical Name: (R)-1-(3-((2-chloro-4-(((2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-5-methoxyphenyl)amino)-3-oxopropyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

InChi Key: URWYQGVSPQJGGB-DHUJRADRSA-N

InChi Code: InChI=1S/C40H42ClN5O7/c1-52-36-22-33(31(41)21-26(36)23-42-24-35(48)29-11-13-34(47)39-30(29)12-14-37(49)45-39)43-38(50)17-20-46-18-15-27(16-19-46)53-40(51)44-32-10-6-5-9-28(32)25-7-3-2-4-8-25/h2-14,21-22,27,35,42,47-48H,15-20,23-24H2,1H3,(H,43,50)(H,44,51)(H,45,49)/t35-/m0/s1

SMILES Code: O=C(OC1CCN(CCC(NC2=CC(OC)=C(CNC[C@H](O)C3=CC=C(O)C4=C3C=CC(N4)=O)C=C2Cl)=O)CC1)NC5=CC=CC=C5C6=CC=CC=C6


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information


References

1: Ambery CL, Wielders P, Ludwig-Sengpiel A, Chan R, Riley JH. Population Pharmacokinetics and Pharmacodynamics of GSK961081 (Batefenterol), a Muscarinic Antagonist and β2-Agonist, in Moderate-to-Severe COPD Patients: Substudy of a Randomized Trial. Drugs R D. 2015 Sep;15(3):281-91. doi: 10.1007/s40268-015-0104-x. PubMed PMID: 26286203; PubMed Central PMCID: PMC4561049.

2: Hughes AD, Chen Y, Hegde SS, Jasper JR, Jaw-Tsai S, Lee TW, McNamara A, Pulido-Rios MT, Steinfeld T, Mammen M. Discovery of (R)-1-(3-((2-chloro-4-(((2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)et hyl)amino)methyl)-5-methoxyphenyl)amino)-3-oxopropyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate (TD-5959, GSK961081, batefenterol): first-in-class dual pharmacology multivalent muscarinic antagonist and β₂ agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD). J Med Chem. 2015 Mar 26;58(6):2609-22. doi: 10.1021/jm501915g. Epub 2015 Feb 9. PubMed PMID: 25629394.

3: Norris V, Ambery C. Use of propranolol blockade to explore the pharmacology of GSK961081, a bi-functional bronchodilator, in healthy volunteers: results from two randomized trials. Drugs R D. 2014 Dec;14(4):241-51. doi: 10.1007/s40268-014-0060-x. PubMed PMID: 25265895; PubMed Central PMCID: PMC4269816.

4: Hegde SS, Hughes AD, Chen Y, Steinfeld T, Jasper JR, Lee TW, McNamara A, Martin WJ, Pulido-Rios MT, Mammen M. Pharmacologic characterization of GSK-961081 (TD-5959), a first-in-class inhaled bifunctional bronchodilator possessing muscarinic receptor antagonist and β2-adrenoceptor agonist properties. J Pharmacol Exp Ther. 2014 Oct;351(1):190-9. doi: 10.1124/jpet.114.216861. Epub 2014 Aug 6. PubMed PMID: 25100753.

5: Cazzola M, Lopez-Campos JL, Puente-Maestu L. The MABA approach: a new option to improve bronchodilator therapy. Eur Respir J. 2013 Oct;42(4):885-7. doi: 10.1183/09031936.00067013. PubMed PMID: 24081753.

6: Bateman ED, Kornmann O, Ambery C, Norris V. Pharmacodynamics of GSK961081, a bi-functional molecule, in patients with COPD. Pulm Pharmacol Ther. 2013 Oct;26(5):581-7. doi: 10.1016/j.pupt.2013.03.015. Epub 2013 Mar 26. PubMed PMID: 23538170.

7: Norris V, Ambery C. Bronchodilation and safety of supratherapeutic doses of salbutamol or ipratropium bromide added to single dose GSK961081 in patients with moderate to severe COPD. Pulm Pharmacol Ther. 2013 Oct;26(5):574-80. doi: 10.1016/j.pupt.2013.03.009. Epub 2013 Mar 21. PubMed PMID: 23524017.

8: Wielders PL, Ludwig-Sengpiel A, Locantore N, Baggen S, Chan R, Riley JH. A new class of bronchodilator improves lung function in COPD: a trial with GSK961081. Eur Respir J. 2013 Oct;42(4):972-81. doi: 10.1183/09031936.00165712. Epub 2013 Feb 21. PubMed PMID: 23429913; PubMed Central PMCID: PMC3787816.

9: Cazzola M, Page C, Matera MG. Long-acting muscarinic receptor antagonists for the treatment of respiratory disease. Pulm Pharmacol Ther. 2013 Jun;26(3):307-17. doi: 10.1016/j.pupt.2012.12.006. Epub 2012 Dec 27. Review. PubMed PMID: 23274274.