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).
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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

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View more information in the IUPHAR Pharmacology Education Project: phenylephrine

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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 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.

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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
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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.

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/)

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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/)
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of nasal congestion. Phenylephrine was originally approved by the FDA in 1952 as phenylephrine hydrochloride in combination with codeine phosphate and promethazine hydrochloride as active ingredients. Phenylephrine hydrochloride was approved by the FDA in 2012. This drug is most commonly found in brand mixtures used to alleviate cold and flu symptoms. On its own, the drug is found in nasal decongestants.
In 2001, the EMA granted orphan designation for phenylephrine hydrochloride for the treatment of ileal pouch anal anastomosis related faecal incontinence [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Phenylephrine is an agonist of α1-adrenoceptors. Nasal decongestant action is mediated by activation of α1-adrenoceptors in the arterioles of the nasal mucosa. This causes vasoconstriction, which leads to decreased edema and increased drainage of the sinus cavities. For the treatment of anastomosis related faecal incontinence, phenylephrine causes α1-adrenoceptor-mediated constriction of smooth muscle of the internal anal sphincter, which helps lessen incontinence.
External links Click here for help
For extended ADME data see the following:

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