cyclobenzaprine   

GtoPdb Ligand ID: 7152

Synonyms: Amrix® | Fexmid | MK-130
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.
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2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
No information available.
Summary of Clinical Use
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 III clinical trials as a therepy for fibromyalgia (June 2015), a common, diffucult to treat chronic pain condition. An additional Phase III trial is recruiting patients with various muscular, neuromuscular, nervous system and rheumatic diseases (NCT02436096). A Phase II trial in military personnel suffering from post-traumatic stress disorder (PTSD) is also underway (see NCT02277704).
Mechanism Of Action and Pharmacodynamic Effects
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.
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