Vilanterol Trifenatate | CAS#503070-58-4 | Beta-2 Agonist

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

MedKoo CAT#: 314240

CAS#: 503070-58-4 (trifenatate)

Description: Vilanterol, also known as GW-642444, is a long-acting beta-2 agonist. It selectively induces cAMP accumulation in CHO cells expressing the β2-AR over the β1- and β3-ARs (EC50s = 0.4, 398, and 794 nM for the human receptors, respectively). Vilanterol inhibits contractions induced by electrical stimulation in isolated superfused guinea pig trachea strips. It inhibits bronchospasms induced by histamine. Formulations containing vilanterol, in combination with fluticasone, have been used in the treatment of chronic obstructive pulmonary disease (COPD) and asthma.

Chemical Structure

Vilanterol trifenatate

CAS# 503070-58-4 (trifenatate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 314240
Name: Vilanterol trifenatate
CAS#: 503070-58-4 (trifenatate)
Chemical Formula: C44H49Cl2NO
Exact Mass: 485.17
Molecular Weight: 774.776
Elemental Analysis: C, 68.21; H, 6.38; Cl, 9.15; N, 1.81; O, 14.45

Price and Availability

Size	Price	Availability
10mg	USD 150	Ready to ship
25mg	USD 250	Ready to ship
50mg	USD 450	Ready to ship
100mg	USD 750	Ready to ship
200mg	USD 1350	Ready to ship
500mg	USD 2650	Ready to ship
1g	USD 3650	Ready to ship
2g	USD 6450	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: GW-642444; GW642444; GW-642444; GW 642444X; Vilanterol; Vilanterol trifenatate.

IUPAC/Chemical Name: (R)-4-(2-((6-(2-((2,6-dichlorobenzyl)oxy)ethoxy)hexyl)amino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol, 2,2,2-triphenylacetic acid (1:1)

InChi Key: KLOLZALDXGTNQE-JIDHJSLPSA-N

InChi Code: InChI=1S/C24H33Cl2NO5.C20H16O2/c25-21-6-5-7-22(26)20(21)17-32-13-12-31-11-4-2-1-3-10-27-15-24(30)18-8-9-23(29)19(14-18)16-28;21-19(22)20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h5-9,14,24,27-30H,1-4,10-13,15-17H2;1-15H,(H,21,22)/t24-;/m0./s1

SMILES Code: OC1=CC=C([C@@H](O)CNCCCCCCOCCOCC2=C(Cl)C=CC=C2Cl)C=C1CO.O=C(O)C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5

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# 503070-58-4 ( Vilantero trifenatate); 503068-34-6 ( Vilantero free base)

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#C8R03B06

QC Data:

View QC data: current batch, Lot#C8R03B06

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Vilanterol trifenatate (GW642444 trifenatate) is a long-acting β2-adrenoceptor (β2-AR) agonist with inherent 24-hour activity.
In vitro activity:	N/A
In vivo activity:	N/A

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	129.07
	Ethanol	14.0	18.07

Preparing Stock Solutions

The following data is based on the product molecular weight 774.78 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

Formulation protocol:	N/A
In vitro protocol:	N/A
In vivo protocol:	N/A

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1: Albertson TE, Richards JR, Zeki AA. The combination of fluticasone furoate and vilanterol trifenatate in the management of asthma: clinical trial evidence and experience. Ther Adv Respir Dis. 2016 Feb;10(1):43-56. doi: 10.1177/1753465815619136. Epub 2015 Dec 14. Review. PubMed PMID: 26668137.

2: Wolthers OD. Pharmacokinetics and Systemic Activity of a New Patent of an Inhaled Corticosteroid/Long-Acting β2-Agonist Combination for Use in Asthma Therapy: Fluticasone Furoate/Vilanterol Trifenatate. Recent Pat Inflamm Allergy Drug Discov. 2015;9(2):144-50. PubMed PMID: 26581314.

3: Spyratos D, Sichletidis L. Umeclidinium bromide/vilanterol combination in the treatment of chronic obstructive pulmonary disease: a review. Ther Clin Risk Manag. 2015 Mar 25;11:481-7. doi: 10.2147/TCRM.S67491. eCollection 2015. Review. PubMed PMID: 25848294; PubMed Central PMCID: PMC4378877.

4: Albertson TE, Harper R, Murin S, Sandrock C. Patient considerations in the treatment of COPD: focus on the new combination inhaler umeclidinium/vilanterol. Patient Prefer Adherence. 2015 Feb 2;9:235-42. doi: 10.2147/PPA.S71535. eCollection 2015. Review. PubMed PMID: 25673975; PubMed Central PMCID: PMC4321647.

5: Relvar Ellipta for asthma. Drug Ther Bull. 2014 Aug;52(8):93-6. doi: 10.1136/dtb.2014.8.0273. Review. PubMed PMID: 25125553.

6: Hussar DA, Dharsi N. Umeclidinium bromide/vilanterol trifenatate, perampanel, and eslicarbazepine acetate. J Am Pharm Assoc (2003). 2014 Jul-Aug;54(4):450-2, 454-5. doi: 10.1331/JAPhA.2014.14527. PubMed PMID: 25063267.

7: Malerba M, Morjaria JB, Radaeli A. Differential pharmacology and clinical utility of emerging combination treatments in the management of COPD--role of umeclidinium/vilanterol. Int J Chron Obstruct Pulmon Dis. 2014 Jun 27;9:687-95. doi: 10.2147/COPD.S47792. eCollection 2014. Review. PubMed PMID: 25061288; PubMed Central PMCID: PMC4085305.

8: Cada DJ, Ingram K, Leonard J, Baker DE. Umeclidinium bromide and vilanterol trifenatate inhalation powder. Hosp Pharm. 2014 Jun;49(6):554-62. doi: 10.1310/hpj4906-554. PubMed PMID: 24958974; PubMed Central PMCID: PMC4062736.

9: ▼Relvar Ellipta for COPD. Drug Ther Bull. 2014 Jun;52(6):66-9. doi: 10.1136/dtb.2014.6.0258. Epub 2014 Jun 5. PubMed PMID: 24904005.

10: Hussar DA, Ahmad A. Vilanterol trifenatate/fluticasone furoate, lomitapide mesylate, and mipomersen sodium. J Am Pharm Assoc (2003). 2013 Nov-Dec;53(6):662-70. doi: 10.1331/JAPhA.2013.13538. PubMed PMID: 24185435.

11: Agustí A, de Teresa L, De Backer W, Zvarich MT, Locantore N, Barnes N, Bourbeau J, Crim C. A comparison of the efficacy and safety of once-daily fluticasone furoate/vilanterol with twice-daily fluticasone propionate/salmeterol in moderate to very severe COPD. Eur Respir J. 2014 Mar;43(3):763-72. doi: 10.1183/09031936.00054213. Epub 2013 Oct 10. PubMed PMID: 24114969.

12: Kempsford R, Norris V, Siederer S. Vilanterol trifenatate, a novel inhaled long-acting beta2 adrenoceptor agonist, is well tolerated in healthy subjects and demonstrates prolonged bronchodilation in subjects with asthma and COPD. Pulm Pharmacol Ther. 2013 Apr;26(2):256-64. doi: 10.1016/j.pupt.2012.12.001. Epub 2012 Dec 8. PubMed PMID: 23232038.

13: Slack RJ, Barrett VJ, Morrison VS, Sturton RG, Emmons AJ, Ford AJ, Knowles RG. In vitro pharmacological characterization of vilanterol, a novel long-acting β2-adrenoceptor agonist with 24-hour duration of action. J Pharmacol Exp Ther. 2013 Jan;344(1):218-30. doi: 10.1124/jpet.112.198481. Epub 2012 Nov 6. PubMed PMID: 23131596.

14: Kempsford R, Allen A, Bal J, Rubin D, Tombs L. The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of inhaled fluticasone furoate and vilanterol trifenatate in healthy subjects. Br J Clin Pharmacol. 2013 Jun;75(6):1478-87. doi: 10.1111/bcp.12019. PubMed PMID: 23116485; PubMed Central PMCID: PMC3690106.

15: Lötvall J, Bateman ED, Bleecker ER, Busse WW, Woodcock A, Follows R, Lim J, Stone S, Jacques L, Haumann B. 24-h duration of the novel LABA vilanterol trifenatate in asthma patients treated with inhaled corticosteroids. Eur Respir J. 2012 Sep;40(3):570-9. doi: 10.1183/09031936.00121411. Epub 2012 Feb 23. PubMed PMID: 22362859.

16: Busse WW, Bleecker ER, Bateman ED, Lötvall J, Forth R, Davis AM, Jacques L, Haumann B, Woodcock A. Fluticasone furoate demonstrates efficacy in patients with asthma symptomatic on medium doses of inhaled corticosteroid therapy: an 8-week, randomised, placebo-controlled trial. Thorax. 2012 Jan;67(1):35-41. doi: 10.1136/thoraxjnl-2011-200308. Epub 2011 Aug 9. PubMed PMID: 21828231.

17: 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.

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Vilanterol trifenatate featured