Structure via PubChem · Public domain (PubChem)
cyclobenzaprine
Sign in to saveAlso known as Amrix®, Fexmid, MK-130, N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-Delta(5,gamma)-propylamine, Ciclobenzaprina, N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-delta(5,gamma)-propylamine, N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-Δ5,γ-propylamine
Cyclobenzaprine, sold under several brand names including, historically, Flexeril, is a muscle relaxer used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth.
Key facts
- Drug.verifiedrevid
- 460109805
- Drug.image
- Cyclobenzaprine.svg
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Flexeril, Amrix, others
- Drug.MedlinePlus
- a682514
- Drug.DailyMedID
- Cyclobenzaprine
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- M03
- Drug.ATC_suffix
- BX08
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- 33–55%
- Drug.protein_bound
- 93%
- Drug.metabolism
- major: CYP3A4, CYP1A2; minor: CYP2D6, N-demethylation
- Drug.metabolites
- Norcyclobenzaprine
- Drug.elimination_half life
- 32 hours (extended-release, range 8–37 hours), 18 hours (immediate release, range 8–37 hours)
- Drug.excretion
- Kidney
- Drug.CAS_number
- 303-53-7
via Wikipedia infobox
Chemical data
- Formula
- C20H21N
- Molecular weight
- 275.4 g/mol
- IUPAC name
- N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)propan-1-amine
- SMILES
- CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C31
- InChIKey
- JURKNVYFZMSNLP-UHFFFAOYSA-N
- XLogP
- 5.2
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
403 papers- Cyclobenzaprine.2012
- Cyclobenzaprine.2006
- Efficacy and Safety of Sublingual Cyclobenzaprine for the Treatment of Fibromyalgia: Results From a Randomized, Double-Blind, Placebo-Controlled Trial.Arthritis care & research · 2023
- Cyclobenzaprine.2026
- Sublingual Cyclobenzaprine: First Approval.Clinical drug investigation · 2026
via PubMed
~10 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Comparison to other medications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Society and culture
- Formulations
- Research
- Fibromyalgia
- References
- External links
Cyclobenzaprine, sold under several brand names including, historically, Flexeril, is a muscle relaxer used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth.
Common side effects include headache, tiredness, dizziness, and dry mouth. Serious side effects may include an irregular heartbeat. There is no evidence of harm in pregnancy, but it has not been well studied in this population. It should not be used together with MAOIs. How it works is unclear. In any case, it is known to inhibit serotonin and norepinephrine reuptake and to block serotonin, adrenergic, histamine, and muscarinic acetylcholine receptors. Chemically, it is very similar to tricyclic antidepressants like amitriptyline.
Excerpted from Wikipedia’s “cyclobenzaprine” article, available under the CC BY-SA 4.0 licence.