phenylephrine   Click here for help

GtoPdb Ligand ID: 485

Synonyms: m-oxedrine | metasynephrine
Approved drug
phenylephrine is an approved drug (FDA (1952))
Compound class: Synthetic organic
Comment: Marketed formulations may contain phenylephrine hydrochloride (PubChem CID 5284443).
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: phenylephrine

phenylephrine is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 52.49
Molecular weight 167.09
XLogP 0.52
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CNCC(c1cccc(c1)O)O
Isomeric SMILES CNC[C@@H](c1cccc(c1)O)O
InChI InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChI Key SONNWYBIRXJNDC-VIFPVBQESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. da Silva Junior ED, Sato M, Merlin J, Broxton N, Hutchinson DS, Ventura S, Evans BA, Summers RJ. (2017)
Factors influencing biased agonism in recombinant cells expressing the human α1A -adrenoceptor.
Br J Pharmacol, 174 (14): 2318-2333. [PMID:28444738]
2. EMA. 
EU/3/01/069- orphan designation for phenylephrine hydrochloride.
Accessed on 28/01/2019. Modified on 28/01/2019. www.ema.europa.eu, https://www.ema.europa.eu/en/medicines/human/orphan-designations/eu301069
3. Evans BA, Broxton N, Merlin J, Sato M, Hutchinson DS, Christopoulos A, Summers RJ. (2011)
Quantification of functional selectivity at the human α(1A)-adrenoceptor.
Mol Pharmacol, 79 (2): 298-307. [PMID:20978120]
4. Ford AP, Daniels DV, Chang DJ, Gever JR, Jasper JR, Lesnick JD, Clarke DE. (1997)
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.
Br J Pharmacol, 121 (6): 1127-35. [PMID:9249248]
5. Minneman KP, Theroux TL, Hollinger S, Han C, Esbenshade TA. (1994)
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
Mol Pharmacol, 46 (5): 929-36. [PMID:7969082]
6. Proudman RGW, Baker JG. (2021)
The selectivity of α-adrenoceptor agonists for the human α1A, α1B, and α1D-adrenoceptors.
Pharmacol Res Perspect, 9 (4): e00799. [PMID:34355529]
7. Taniguchi T, Inagaki R, Murata S, Akiba I, Muramatsu I. (1999)
Microphysiometric analysis of human alpha1a-adrenoceptor expressed in Chinese hamster ovary cells.
Br J Pharmacol, 127 (4): 962-8. [PMID:10433504]