cyclobenzaprine   Click here for help

GtoPdb Ligand ID: 7152

Synonyms: Amrix® | Fexmid | MK-130
Approved drug
cyclobenzaprine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Cyclobenzaprine is a tricyclic antidepressant similar to amitriptyline. It acts as a skeletal muscle relaxant and central nervous system (CNS) depressant.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cyclobenzaprine

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 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 3.24
Molecular weight 275.17
XLogP 5.21
No. Lipinski's rules broken 1

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 CN(CCC=C1c2ccccc2C=Cc2c1cccc2)C
Isomeric SMILES CN(CCC=C1c2ccccc2C=Cc2c1cccc2)C
InChI InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3
InChI Key JURKNVYFZMSNLP-UHFFFAOYSA-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
This drug is used to relieve muscle spasm associated with acute musculoskeletal pain. A sublingually administered formulation of cyclobenzaprine hydrochloride (TNX-102, PubChem CID 22576) is being evaluated in Phase 2I clinical trials as a therepy for fibromyalgia (June 2015), a common, diffucult to treat chronic pain condition. An additional Phase 2I trial is recruiting patients with various muscular, neuromuscular, nervous system and rheumatic diseases (NCT02436096). A Phase 2 trial in military personnel suffering from post-traumatic stress disorder (PTSD) is also underway (see NCT02277704).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cyclobenzaprine antagonises central serotonin 5-HT2A and 5-HT2C receptors. This decreases activity in serotonergic neurones innervating the muscle and results in reduced muscle tone.
External links Click here for help
For extended ADME data see the following:

Drugs.com