levorphanol   Click here for help

GtoPdb Ligand ID: 7595

Synonyms: (-) 3-hydroxy-N-methylmorphinan | Levo-Dromoran® | levorphanol hydrochloride | levorphanol tartrate
Approved drug
levorphanol is an approved drug (FDA (1953))
Compound class: Synthetic organic
Comment: Levorphanol is an opioid analgesic. Chemically it is the levorotatory optical isomer of racemorphan (PubChem CID 3918).
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
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 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.

✖
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 23.47
Molecular weight 257.18
XLogP 3.29
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES Oc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
Isomeric SMILES Oc1ccc2c(c1)[C@]13CCCC[C@H]3[C@@H](C2)N(CC1)C
InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
InChI Key JAQUASYNZVUNQP-USXIJHARSA-N
No information available.
Summary of Clinical Use Click here for help
Used to treat moderate to severe pain, including potentially, neuropathic pain [3].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Levorphanol is a μ opioid receptor agonist. Activation of this receptor on central nervous system neurons inhibits intracellular adenylate cyclase. Downstream this leads to reduced calcium influx via membrane calcium channels, and increased potassium permeability by opening membrane potassium channels. This ultimately leads to hyperpolarization of the cell membrane potential and suppression of action potential transmission of ascending pain pathways. Antagonist activity at NMDA receptors may be useful in the treatment of neuropathic pain which is unresponsive to other pain medications [3].
External links Click here for help
For extended ADME data see the following:

Drugs.com