naloxone   Click here for help

GtoPdb Ligand ID: 1638

Synonyms: (-)-naloxone | Kloxxado® (naloxone hydrochloride nasal spray) | l-naloxone | Narcan® | Nyxoid®
Approved drug PDB Ligand
naloxone is an approved drug (FDA (1971), EMA (2017))
Compound class: Synthetic organic
Comment: The approved drug naloxone INN-assigned preparation is the (-)-enantiomer. For a summary of the (+)-enantiomer, see the ligand page for (+)-naloxone. (-)-naloxone is the active enantiomer. The (+) isomer is inactive at the opioid receptors.
Marketed formulations may contain naloxone hydrochloride (PubChem CID 5464092).
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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: naloxone

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 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 70
Molecular weight 327.15
XLogP 0.31
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 C=CCN1CCC23C4(C1Cc1c3c(OC2C(=O)CC4)c(cc1)O)O
Isomeric SMILES C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O
InChI InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
InChI Key UZHSEJADLWPNLE-GRGSLBFTSA-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 to reverse narcotic depression, including respiratory depression induced by opioids. Also indicated for the diagnosis of acute opioid overdose and as an adjunctive agent to increase blood pressure following septic shock.
Naloxone is sometimes combined in fixed-mixture brands with opioid analgesics as a method of deterring abuse of opioid medications. Naloxone blocks the euphoric effects of the opioid, making it less attractive to drug abusers. Examples of such combinations are Targiniq ER® which contains oxycodone hydrochloride and naloxone hydrochloride and Suboxone® and Zubsolv® which contain naloxone and buprenorphine. Targiniq ER® is used as a pain medication in specific patients, whereas Suboxone® and Zubsolv® are used to treat opiate dependence.
In September 2014 the US FDA approved Contrave® (bupropion and naloxone), a fixed-mixture medication, to be used in conjunction with reduced-calorie intake and physical activity, as a treatment for chronic weight management.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The exact mechanism of action of naloxone is unknown, but its properties are believed to arise from its antagonism of opioid receptors.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)