Abediterol

Chemical compound

None

Pharmacokinetic dataElimination half-life24.3 hours^[1]Identifiers

IUPAC name

5-[(1R)-2-{[6-(2,2-Difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl]-8-hydroxyquinolin-2(1H)-one

CAS Number

915133-65-2

PubChem CID

11962616

IUPHAR/BPS

9326

ChemSpider

10136846^Y

UNII

QXA167CM6F

KEGG

D10219^Y

ChEBI

CHEBI:142077

ChEMBL

ChEMBL3039530^Y

CompTox Dashboard (EPA)

DTXSID60238605

Chemical and physical dataFormulaC₂₅H₃₀F₂N₂O₄Molar mass460.522 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

FC(F)(c1ccccc1)COCCCCCCNC[C@H](O)c3ccc(O)c2c3\C=C/C(=O)N2

InChI

InChI=1S/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1^Y
Key:SFYAXIFVXBKRPK-QFIPXVFZSA-N^Y

Abediterol (INN;^[2] development codes AZD-0548 and LAS 100977) is a once-daily experimental drug candidate for the treatment of asthma and chronic obstructive pulmonary disease (COPD), but it has never been marketed.

History

Abediterol was under development by the Spanish pharmaceutical company Almirall and reached Phase II clinical trials,^[3]^[4] but was discontinued in 2021.^[5] Its coformulation with mometasone furoate also progressed to Phase II clinical trials, but was discontinued in 2019.^[6]

Mechanism of action

Abediterol acts as a dual β₂ adrenergic agonist^[7]^[8] and muscarinic antagonist and is classified as an ultra-long-acting β₂ agonist (ultra-LABA).^[9]

References

^ Timmer W, Massana E, Jimenez E, Seoane B, de Miquel G, Ruiz S (December 2014). "First-in-human study of the safety, tolerability, pharmacokinetics and pharmacodynamics of abediterol (LAS100977), a novel long-acting Β2 -agonist". Journal of Clinical Pharmacology. 54 (12): 1347–53. doi:10.1002/jcph.355. PMID 24989946. S2CID 20959248.
^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed International Nonproprietary Names: List 104" (PDF). WHO Drug Information. 24 (1): 352. 2010. Retrieved 25 March 2016.
^ Product development pipeline, Almirall
^ "AdisInsight: Abediterol". Adis Insight. Springer International Publishing AG. Retrieved 25 March 2016.
^ "Abediterol". Adis Insight. Springer International Publishing AG. Retrieved 6 February 2024.
^ "AdisInsight: Abediterol/mometasone". Adis Insight. Springer International Publishing AG. Retrieved 6 February 2024.
^ "Espacenet - Bibliographic data". worldwide.espacenet.com. Retrieved 2021-05-07.
^ "Espacenet - Bibliographic data". worldwide.espacenet.com. Retrieved 2021-05-07.
^ Beier J, Fuhr R, Massana E, Jiménez E, Seoane B, de Miquel G, Ruiz S (October 2014). "Abediterol (LAS100977), a novel long-acting β2-agonist: efficacy, safety and tolerability in persistent asthma". Respiratory Medicine. 108 (10): 1424–9. doi:10.1016/j.rmed.2014.08.005. PMID 25256258.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast