salmeterol   Click here for help

GtoPdb Ligand ID: 559

Synonyms: GR 33343X | Serevent®
Approved drug Immunopharmacology Ligand
salmeterol is an approved drug (FDA (1994), EMA (2016))
Compound class: Synthetic organic
Comment: Marketed formulations may contain salmeterol xinafoate (PubChem CID 56801).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 16
Topological polar surface area 81.95
Molecular weight 415.27
XLogP 4.18
No. Lipinski's rules broken 1
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Canonical SMILES OCc1cc(ccc1O)C(CNCCCCCCOCCCCc1ccccc1)O
Isomeric SMILES OCc1cc(ccc1O)C(CNCCCCCCOCCCCc1ccccc1)O
InChI InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2
1. Baker JG. (2010)
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.
Br J Pharmacol, 160 (5): 1048-61. [PMID:20590599]
2. Baker JG, Proudman RG, Hill SJ. (2015)
Salmeterol's extreme β2 selectivity is due to residues in both extracellular loops and transmembrane domains.
Mol Pharmacol, 87 (1): 103-20. [PMID:25324048]
3. Battram C, Charlton SJ, Cuenoud B, Dowling MR, Fairhurst RA, Farr D, Fozard JR, Leighton-Davies JR, Lewis CA, McEvoy L et al.. (2006)
In vitro and in vivo pharmacological characterization of 5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one (indacaterol), a novel inhaled beta(2) adrenoceptor agonist with a 24-h duration of action.
J Pharmacol Exp Ther, 317 (2): 762-70. [PMID:16434564]
4. De Pascali F, Ippolito M, Wolfe E, Komolov KE, Hopfinger N, Lemenze D, Kim N, Armen RS, An SS, Scott CP et al.. (2022)
β2 -Adrenoceptor agonist profiling reveals biased signalling phenotypes for the β2 -adrenoceptor with possible implications for the treatment of asthma.
Br J Pharmacol, 179 (19): 4692-4708. [PMID:35732075]