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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
Cyclobenzaprine and back pain: a meta-analysis.
2001 Jul 9
Cyclobenzaprine hydrochloride is a commonly prescribed centrally acting muscle relaxant, which is structurally similar to tricyclic antidepressants (TCAs) and differs from amitriptyline by only one double bond.
2001 Mar
Clinical inquiries. What is the most effective treatment for acute low back pain?
2002 Feb
Cyclobenzaprine pharmacokinetics, including the effects of age, gender, and hepatic insufficiency.
2002 Jan
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
A randomized clinical trial comparing chiropractic adjustments to muscle relaxants for subacute low back pain.
2004 Jul-Aug
Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone.
2004 Sep
Variability in tablet fragment weights when splitting unscored cyclobenzaprine 10 mg tablets.
2004 Sep-Oct
Interactions of cyclobenzaprine and tricyclic antidepressants.
2005 Jan
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
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs.
2006 Dec
Shift work and pathological conditions.
2006 Dec 11
Anticholinergic esotropia.
2008 Dec
Elderly patient refractory to multiple pain medications successfully treated with integrative East-West medicine.
2008 Nov 30
Insights in to the pathogenesis of axial spondyloarthropathy based on gene expression profiles.
2009
Comparison of the single-dose pharmacokinetics of once-daily cyclobenzaprine extended-release 30 mg and cyclobenzaprine immediate-release 10 mg three times daily in the elderly: a randomized, open-label, crossover study.
2009
Plasmapheresis in a patient with rhabdomyolysis: a case report.
2009 Aug 12
A 19-month-old girl with recurrent illness: over the hills and through the woods.
2009 Dec
Rhabdomyolysis associated with the nutritional supplement Hydroxycut.
2009 Jan 15
Cyclobenzaprine for the treatment of myofascial pain in adults.
2009 Jul 8
Is there sufficient evidence to suggest cyclobenzaprine might be implicated in causing serotonin toxicity?
2009 May
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Comparison of ibuprofen, cyclobenzaprine or both in patients with acute cervical strain: a randomized controlled trial.
2010 Jan
Evidence that tricyclic small molecules may possess toll-like receptor and myeloid differentiation protein 2 activity.
2010 Jun 30
Case files of the California poison control system, San Francisco division: blue thunder ingestion: methanol, nitromethane, and elevated creatinine.
2010 Mar
Antidepressant drugs in oral fluid using liquid chromatography-tandem mass spectrometry.
2010 Mar
Impact of poor-quality medicines in the 'developing' world.
2010 Mar
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