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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21N
Molecular Weight 275.3882
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOBENZAPRINE

SMILES

CN(C)CCC=C1c2ccccc2C=Cc3ccccc31

InChI

InChIKey=JURKNVYFZMSNLP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/slideshow/flexeril-cyclobenzaprine-muscle-relaxants-1266 | http://www.rxlist.com/flexeril-drug.htm | https://www.ncbi.nlm.nih.gov/pubmed/26926618 | https://www.ncbi.nlm.nih.gov/pubmed/26668287

Cyclobenzaprine is a centrally-acting muscle relaxant which boosts levels of norepinephrine and binds to serotonin receptors in the brain to reduce spasm. Cytochromes P-450 3A4, 1A2, and, to a lesser extent, 2D6, mediate N-demethylation, one of the oxidative pathways for cyclobenzaprine. Cyclobenzaprine relieves skeletal muscle spasm of local origin without interfering with muscle function. Drowsiness, fatigue and sedation (up to 40%) is the most common side effect of Cyclobenzaprine. It may have life-threatening interactions with monoamine oxidase (MAO) inhibitors. Postmarketing cases of serotonin syndrome have been reported during combined use of cyclobenzaprine and other drugs such as selective serotonin reuptake inhibitors (SSRIs), serotonin norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), tramadol, bupropion, meperidine, verapamil, or MAO inhibitors.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CYCLOBENZAPRINE HYDROCHLORIDE

Approved Use

Drug is indicated as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions. Improvement is manifested by relief of muscle spasm and its associated signs and symptoms, namely, pain, tenderness, limitation of motion, and restriction in activities of daily living.

Launch Date

5.7300478E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.3 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOBENZAPRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
354.1 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOBENZAPRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
33.4 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOBENZAPRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources: Page: p.282
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.282
Disc. AE: Lethargy, Slurred speech...
AEs leading to
discontinuation/dose reduction:
Lethargy
Slurred speech
Sinus tachycardia
Sources: Page: p.282
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Disc. AE: Sinus tachycardia, Confusion...
AEs leading to
discontinuation/dose reduction:
Sinus tachycardia
Confusion
Drowsiness
Agitation
Visual hallucinations
Sources: Page: p.283
10 mg 3 times / day multiple, oral
Recommended
Dose: 10 mg, 3 times / day
Route: oral
Route: multiple
Dose: 10 mg, 3 times / day
Sources: Page: p.1068
unhealthy, 41.5
n = 249
Health Status: unhealthy
Condition: Muscle spasm
Age Group: 41.5
Sex: M+F
Population Size: 249
Sources: Page: p.1068
Disc. AE: Somnolence...
AEs leading to
discontinuation/dose reduction:
Somnolence (5.2%)
Sources: Page: p.1068
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Muscle spasm
Sources: Page: p.1
Disc. AE: Serotonin syndrome, Cardiovascular disorder NOS...
AEs leading to
discontinuation/dose reduction:
Serotonin syndrome (grade 4)
Cardiovascular disorder NOS
CNS depression
Sources: Page: p.1
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Other AEs: Tachycardia, Dry mouth...
Other AEs:
Tachycardia (below serious, 1 patient)
Dry mouth (below serious, 6 patients)
Toothache (below serious, 1 patient)
Rhinitis (below serious, 1 patient)
Dizziness (below serious, 1 patient)
Dysgeusia (below serious, 1 patient)
Anxiety (below serious, 1 patient)
Disruptive mood dysregulation disorder (below serious, 1 patient)
Sleep disorder (below serious, 1 patient)
Somnolence (below serious, 18 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Lethargy Disc. AE
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources: Page: p.282
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.282
Sinus tachycardia Disc. AE
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources: Page: p.282
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.282
Slurred speech Disc. AE
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources: Page: p.282
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.282
Agitation Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Confusion Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Drowsiness Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Sinus tachycardia Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Visual hallucinations Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources: Page: p.283
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: F
Population Size: 1
Sources: Page: p.283
Somnolence 5.2%
Disc. AE
10 mg 3 times / day multiple, oral
Recommended
Dose: 10 mg, 3 times / day
Route: oral
Route: multiple
Dose: 10 mg, 3 times / day
Sources: Page: p.1068
unhealthy, 41.5
n = 249
Health Status: unhealthy
Condition: Muscle spasm
Age Group: 41.5
Sex: M+F
Population Size: 249
Sources: Page: p.1068
CNS depression Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Muscle spasm
Sources: Page: p.1
Cardiovascular disorder NOS Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Muscle spasm
Sources: Page: p.1
Serotonin syndrome grade 4
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Muscle spasm
Sources: Page: p.1
Anxiety below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Disruptive mood dysregulation disorder below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Dizziness below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Dysgeusia below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Rhinitis below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Sleep disorder below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Tachycardia below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Toothache below serious, 1 patient
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Somnolence below serious, 18 patients
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Dry mouth below serious, 6 patients
15 mg 1 times / day steady, oral
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
unhealthy
n = 90
Health Status: unhealthy
Condition: Cervical and/or Lower Back Pain
Population Size: 90
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim
PubMed

PubMed

TitleDatePubMed
Hallucinations in an elderly patient taking recommended doses of cyclobenzaprine.
2000 May 8
Release of cyclobenzaprine hydrochloride from osmotically rupturable tablets.
2002 Jul
The lack of a placebo effect in a trial of fluoxetine in the treatment of fibromyalgia.
2002 Nov
The effectiveness of adding pharmacologic treatment with clonazepam or cyclobenzaprine to patient education and self-care for the treatment of jaw pain upon awakening: a randomized clinical trial.
2002 Winter
Cyclobenzaprine with ibuprofen versus ibuprofen alone in acute myofascial strain: a randomized, double-blind clinical trial.
2003 Jun
Prescription of nonsteroidal anti-inflammatory drugs and muscle relaxants for back pain in the United States.
2004 Dec 1
Human liver aldehyde oxidase: inhibition by 239 drugs.
2004 Jan
Medicinal and injection therapies for mechanical neck disorders.
2005 Apr 18
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Low-dose cyclobenzaprine versus combination therapy with ibuprofen for acute neck or back pain with muscle spasm: a randomized trial.
2005 Sep
Persistent low back pain.
2005 Sep 1
Fatality after deliberate ingestion of sustained-release ibuprofen: a case report.
2006
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs.
2006 Dec
Shift work and pathological conditions.
2006 Dec 11
Rhabdomyolysis: a manifestation of cyclobenzaprine toxicity.
2006 Jul 17
Extended-release cyclobenzaprine (Amrix).
2007 Dec 17
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Do motor control genes contribute to interindividual variability in decreased movement in patients with pain?
2007 Jul 26
Single-dose pharmacokinetics of once-daily cyclobenzaprine extended release 30 mg versus cyclobenzaprine immediate release 10 mg three times daily in healthy young adults : a randomized, open-label, two-period crossover, single-centre study.
2008
A meta-analysis of the efficacy of fibromyalgia treatment according to level of care.
2008
Choosing a skeletal muscle relaxant.
2008 Aug 1
Treatment options and patient perspectives in the management of fibromyalgia: future trends.
2008 Dec
Anticholinergic esotropia.
2008 Dec
Lower facial contouring with botulinum toxin type A.
2008 Nov
Serotonin syndrome in a patient taking Lexapro and Flexeril: a case report.
2008 Nov
Torticollis under cyclobenzaprine.
2009
Plasmapheresis in a patient with rhabdomyolysis: a case report.
2009 Aug 12
Is there sufficient evidence to suggest cyclobenzaprine might be implicated in causing serotonin toxicity?
2009 May
Cyclobenzaprine ER for muscle spasm associated with low back and neck pain: two randomized, double-blind, placebo-controlled studies of identical design.
2009 May
Standardized natural product cannabis in pain management and observations at a Canadian compassion society: a case report.
2009 May 18
Fibromyalgia and myofascial pain syndrome-a dilemma.
2009 Oct
Patients' experiences of living with and receiving treatment for fibromyalgia syndrome: a qualitative study.
2009 Oct 7
Comparison of ibuprofen, cyclobenzaprine or both in patients with acute cervical strain: a randomized controlled trial.
2010 Jan
Efficacy and tolerability of cyclobenzaprine extended release for acute muscle spasm: a pooled analysis.
2010 Jul
Pharmacologic management of chronic pain.
2010 Jun
Impact of poor-quality medicines in the 'developing' world.
2010 Mar
Pharmacokinetic profile of once-daily cyclobenzaprine extended-release.
2010 Nov
Patents

Sample Use Guides

5 mg three times a day. Based on individual patient response, the dose may be increased to either 7.5 mg or 10 mg three times a day.
Route of Administration: Oral
In Vitro Use Guide
The iontaphoretic application of Cyclobenzaprine (CBZ) caused, in all cases, a decrease in discharge rate. This slowing was invariably attended by a marked decrease in action potential amplitude however, and was therefore considered likely to be a local anesthetic effect, even at 5 nA. On the other hand, when CBZ was infused into the chamber to a concentration equivalent to 1 mg/kg for the whole animal, assuming distribution in all extracellular water, all cells responded and no local anesthetic effects were evident. The six cells with initial discharge rates between 2 and 10 Hz decreased firing with CBZ, whereas the four cells with initial rates between 0.5 and 1.5 Hz increased their rates with CBZ.
Name Type Language
CYCLOBENZAPRINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CYCLOBENZAPRINE [MI]
Common Name English
MK-130 (AS THE BASE)
Code English
NORTRIPTYLINE HYDROCHLORIDE IMPURITY E [EP]
Common Name English
MK-130
Systematic Name English
AMITRIPTYLINE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
CYCLOBENZAPRINE [USP]
Common Name English
CYCLOBENZAPRINE [INN]
Common Name English
CYCLOBENZAPRINE [VANDF]
Common Name English
CYCLOBENZAPRINE [WHO-DD]
Common Name English
N,N-DIMETHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-(SUP .DELTA.5,.GAMMA.)-PROPYLAMINE
Common Name English
TNX-102
Code English
1-PROPANAMINE, 3-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-
Systematic Name English
3-(5H-DIBENZO(A,D)(7)ANNULEN-5-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
NDF-RT N0000175737
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
NDF-RT N0000175730
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
WHO-VATC QM03BX08
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
LIVERTOX 247
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
WHO-ATC M03BX08
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
Code System Code Type Description
LACTMED
Cyclobenzaprine
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
EVMPD
SUB06849MIG
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
FDA UNII
69O5WQQ5TI
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
DRUG CENTRAL
751
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
WIKIPEDIA
CYCLOBENZAPRINE
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-145-8
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL669
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
MERCK INDEX
M3976
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY Merck Index
IUPHAR
7152
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
DRUG BANK
DB00924
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
CAS
303-53-7
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
HSDB
8305
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
INN
791
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
MESH
C004704
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
NCI_THESAURUS
C28947
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
RXCUI
21949
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY RxNorm
PUBCHEM
2895
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY
EPA CompTox
303-53-7
Created by admin on Sat Jun 26 10:05:47 UTC 2021 , Edited by admin on Sat Jun 26 10:05:47 UTC 2021
PRIMARY