Vilanterol Trifenatate

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Cat Number

API503070584

CAS Number

503070-58-4

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Product Detail Description Scientific Support Customer Q&A

CAS Number

503070-58-4

EINECS

638-763-2

Storage

Store at room temperature

Synonyms

40AHO2C6DG; GW-642444M; Vilanterol trifenatate [USAN]

Molecular Formula

C44H49Cl2NO7

Molecular Weight

774.8

Smiles

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)O.C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNC[C@@H](C2=CC(=C(C=C2)O)CO)O)Cl

Appearance

White to off-white powder

Melting Point

132-134℃

General Description

Vilanterol trifenatate is an ultra-long-acting beta-2 adrenergic agonist (ultra-LABA) administered by oral inhalation once daily for the management of chronic obstructive pulmonary disease (COPD) and asthma. The trifenatate salt enhances the drug's lipophilicity and facilitates prolonged receptor occupancy. It is available only in fixed-dose combination products, typically with an inhaled corticosteroid such as fluticasone furoate or with an anticholinergic agent.

Mechanism of Action

Vilanterol selectively activates beta-2 adrenergic receptors on airway smooth muscle cells, stimulating intracellular adenylate cyclase to increase cyclic AMP production. Elevated cyclic AMP activates protein kinase A, which phosphorylates multiple targets leading to smooth muscle relaxation and sustained bronchodilation lasting more than 24 hours. The ultra-long duration results from high receptor affinity and slow dissociation kinetics, allowing once-daily administration.

Application

It is indicated for the maintenance treatment of COPD, including chronic bronchitis and emphysema, as well as for the regular treatment of asthma in patients aged 18 years and older. Due to an increased risk of serious asthma-related adverse events when LABAs are used as monotherapy, vilanterol must always be used in combination with an inhaled corticosteroid for asthma. It is not indicated for acute bronchospasm relief, as its onset of action is not sufficiently rapid.

This pooled population pharmacokinetic analysis included 1225 COPD patients and healthy subjects receiving once‑daily fluticasone furoate (FF) and vilanterol (VI). FF data fit a two‑compartment model with first‑order absorption; race was a significant covariate, with East Asians, Japanese, and South‑East Asians having 23–30% higher FF AUC than Caucasians. VI followed a three‑compartment model with zero‑order absorption; age, body weight, sex, and smoking affected VI pharmacokinetics. Despite these statistically significant covariate effects, the magnitude of the differences was not clinically meaningful, and the authors conclude that no dose adjustment is warranted for FF/VI in COPD patients.

Fig. 1 Goodness-of-fit plots for the vilanterol final model in subjects with COPD. (Siederer S, et al., 2016)

References

Siederer S, et al. Population Pharmacokinetics of Inhaled Fluticasone Furoate and Vilanterol in Subjects with Chronic Obstructive Pulmonary Disease. Eur J Drug Metab Pharmacokinet. 2016; 41(6):743-758.

Does Vilanterol Trifenatate require refrigerated storage as a long-acting beta agonist?

No, it is stable at controlled room temperature (15-25°C). Refrigeration is not required, but avoid temperatures above 30°C to prevent degradation of the trifenatate salt.

Is Vilanterol Trifenatate sensitive to moisture, and how is this prevented?

Yes, it is hygroscopic. Storage in tightly sealed, moisture-proof containers with desiccant is essential to prevent hydrolysis and maintain inhalation-grade purity.

What is the stability of Vilanterol Trifenatate in dry powder inhaler blends?

It shows good stability when micronized and blended with lactose. We provide compatibility and stability data for DPI formulations, including protection against moisture.

How is the impurity vilanterol diphenylacetate monitored during stability?

This process-related impurity is quantified using a stability-indicating HPLC method, ensuring it remains below ICH qualification thresholds throughout shelf life.