salbutamol   Click here for help

GtoPdb Ligand ID: 558

Synonyms: albuterol | SCH-13949W | Ventolin®
Approved drug Immunopharmacology Ligand
salbutamol is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: The approved drug salbutamol is a racemic mixture of two enantiomers: levosalbutamol ((R)-salbutamol) and (S)-salbutamol. The structure shown here does not specify stereochemistry and represents the mixture. The US FDA approved this drug with the name albuterol.
Marketed formulations may contain salbutamol sulfate (PubChem CID 9884233).
Salbutamol is termed a 'short-acting beta-agonist' (SABA).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: salbutamol

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 72.72
Molecular weight 239.15
XLogP 1.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCc1cc(ccc1O)C(CNC(C)(C)C)O
Isomeric SMILES OCc1cc(ccc1O)C(CNC(C)(C)C)O
InChI InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3
InChI Key NDAUXUAQIAJITI-UHFFFAOYSA-N
References
1. Baker JG. (2005)
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
Br J Pharmacol, 144 (3): 317-22. [PMID:15655528]
2. 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]
3. 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]
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]
5. Isogaya M, Sugimoto Y, Tanimura R, Tanaka R, Kikkawa H, Nagao T, Kurose H. (1999)
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.
Mol Pharmacol, 56 (5): 875-85. [PMID:10531390]
6. Soriano-Ursúa MA, McNaught-Flores DA, Nieto-Alamilla G, Segura-Cabrera A, Correa-Basurto J, Arias-Montaño JA, Trujillo-Ferrara JG. (2012)
Cell-based and in-silico studies on the high intrinsic activity of two boron-containing salbutamol derivatives at the human β₂-adrenoceptor.
Bioorg Med Chem, 20 (2): 933-41. [PMID:22182578]