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QuickView for Cyclobenzaprine (compound)

Name: cyclobenzaprine
PubChem Compound ID: 22576
Molecular formula: C20H22ClN
Molecular weight: 311.848 g/mol
Lisseril; Flexiban; D00772; 3-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)propyl(dimethyl)ammonium chloride; 1-Propanamine, 3-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride; Prestwick_790; 10,11delta-Amitriptyline hydrochloride; Novo-Cycloprine; N,N-Dimethyl-5H-dibenzo(a,d)cycloheptene-delta(sup 5,gamma)-propylamine hydrochloride; Proheptatriene hydrochloride.
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Name: cyclobenzaprine
Name (isomeric): DB00924
Drug Type: small molecule
Cyclobenzaprine HCL
Brand: Proeptatriene, Cyclobenz, Proheptatriene, Flexiban, Flexeril
Category: Tranquilizing Agents, Muscle Relaxants, Central, Muscle Relaxants, Skeletal Muscle Relaxants, Antidepressive Agents, Tricyclic
CAS number: 303-53-7
Indication: For use as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions.
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.
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 se...
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Absorption: Slowly but well absorbed after oral administration
Protein binding: Very high (93%)
Biotransformation: Extensively metabolized (gastrointestinal and hepatic).
Route of elimination: Cyclobenzaprine is extensively metabolized, and is excreted primarily as glucuronides via the kidney.
Half Life: 18 hours (range 8-37 hours)
Clearance: 0.7 L/min
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.
Affected organisms: Humans and other mammals
Food interaction:
Avoid alcohol.
Take with food to reduce irritation.
Drug interaction:
TriprolidineTriprolidine and Cyclobenzaprine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
DonepezilPossible antagonism of action
TrospiumTrospium and Cyclobenzaprine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TranylcypromineIncreased risk of serotonin syndrome. Concomitant use should be avoided. These agents should not be administered within 14 days of each other.
ThiabendazoleThe strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Cyclobenzaprine by decreasing Cyclobenzaprine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Cyclobenzaprine if Thiabendazole is initiated, discontinued or dose changed.
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