Overview
| Generic Names: | Cyclobenzaprine HCL |
|---|---|
| IUPAC Name: | 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine |
| Trade Names: | Cyclobenz; Flexeril; Flexiban; Proeptatriene; Proheptatriene |
| PharmGKB Accession Id: | PA449160 |
Description
Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. Cyclobenzaprine acts on the locus coeruleus where it results in increased norepinephrine release, potentially through the gamma fibers which innervate and inhibit the alpha motor neurons in the ventral horn of the spinal cord. It is structurally similar to Amitriptyline, differing by only one double bond.
Indication
For use as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions.
ATC Therapeutic Category
- M03BX:Other centrally acting agents
Pharmacology and Interactions
Mechanism Of Action
Like other tricyclic antidepressants, cyclobenzaprine exhibits anticholinergic activity, potentiation of norepinephrine, and antagonism of reserpine. Cyclobenzaprine does not directly act on the neuromuscular junction or the muscle but relieves muscle spasms through a central action, possibly at the brain stem level. Cyclobenzaprine binds to the serotonin receptor and is considered a 5-HT2 receptor antagonist that reduces muscle tone by decreasing the activity of descending serotonergic neurons.
Pharmacology
Cyclobenzaprine, closely related to the antidepressant amitriptyline, is used as a skeletal muscle relaxant to reduce pain and tenderness and improve mobility. Unlike dantrolene, cyclobenzaprine cannot be used to treat muscle spasm secondary to cerebral or spinal cord disease.
Food Interactions
Avoid alcohol. Take with food to reduce irritation.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Extensively metabolized (gastrointestinal and hepatic).
Protein Binding
Very high (93%)
Absorption
Slowly but well absorbed after oral administration
Half Life
18 hours (range 8-37 hours)
Toxicity
Oral mouse and rat LD50 are 338 mg/kg and 425 mg/kg respectively. Signs of overdose include agitation, coma, confusion, congestive heart failure, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high or low temperature, increased heartbeats, irregular heart rhythms, muscle stiffness, overactive reflexes, severe low blood pressure, stupor, and vomiting.
Chemical Properties
Chemical Formula:
C20H21N
SMILES Code:
CN(C)CCC=C1c2ccccc2C=Cc3c1cccc3
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
275.3874 / 275.1674
Curated Information
The following genes are in curated knowledge about this drug.
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CYP1A2 |
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CYP2D6 |
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CYP3A |
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CYP3A4 |
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CYP3A5 |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| donepezil | Possible antagonism of action |
| galantamine | Possible antagonism of action |
| rasagiline | Increased risk of toxicity with this association |
| rivastigmine | Possible antagonism of action |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
Search PubMed
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
