U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H21N.ClH
Molecular Weight 311.848
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOBENZAPRINE HYDROCHLORIDE

SMILES

Cl.CN(C)CCC=C1C2=C(C=CC=C2)C=CC3=C1C=CC=C3

InChI

InChIKey=VXEAYBOGHINOKW-UHFFFAOYSA-N
InChI=1S/C20H21N.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C20H21N
Molecular Weight 275.3874
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Management of sleep disorders in fibromyalgia.
2002 May
Development and use of a computer program to detect potentially inappropriate prescribing in older adults residing in Canadian long-term care facilities.
2002 Oct 14
A randomized clinical trial comparing chiropractic adjustments to muscle relaxants for subacute low back pain.
2004 Jul-Aug
Usage of pain medications during stroke rehabilitation: the Post-Stroke Rehabilitation Outcomes Project (PSROP).
2005 Fall
Interactions of cyclobenzaprine and tricyclic antidepressants.
2005 Jan
Atypical antipsychotics in the treatment of fibromyalgia: a case series with olanzapine.
2005 Jan
Pulmonary embolism in a woman taking oral contraceptives and valdecoxib.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Persistent low back pain.
2005 Sep 1
Biology and therapy of fibromyalgia. New therapies in fibromyalgia.
2006
Fatality after deliberate ingestion of sustained-release ibuprofen: a case report.
2006
Methemoglobinemia: life-threatening hazard of multiple drug ingestions.
2006 Apr-Jun
Shift work and pathological conditions.
2006 Dec 11
Extended-release cyclobenzaprine (Amrix).
2007 Dec 17
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.
2008
A meta-analysis of the efficacy of fibromyalgia treatment according to level of care.
2008
Treatment options and patient perspectives in the management of fibromyalgia: future trends.
2008 Dec
Anticholinergic esotropia.
2008 Dec
Skeletal muscle relaxants.
2008 Feb
Insights in to the pathogenesis of axial spondyloarthropathy based on gene expression profiles.
2009
Effects of naltrexone on pain sensitivity and mood in fibromyalgia: no evidence for endogenous opioid pathophysiology.
2009
Effect of food on the pharmacokinetics of once-daily cyclobenzaprine extended-release 30 mg: a randomized, open-label, crossover, single-centre study.
2009
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.
2009 Apr 28
Rhabdomyolysis associated with the nutritional supplement Hydroxycut.
2009 Jan 15
Cyclobenzaprine ER for muscle spasm associated with low back and neck pain: two randomized, double-blind, placebo-controlled studies of identical design.
2009 May
Pharmacotherapy of chronic pain: a synthesis of recommendations from systematic reviews.
2009 May-Jun
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
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
Antidepressant drugs in oral fluid using liquid chromatography-tandem mass spectrometry.
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:01:55 UTC 2023
Edited
by admin
on Wed Jul 05 23:01:55 UTC 2023
Record UNII
0VE05JYS2P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOBENZAPRINE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
1-PROPANAMINE, 3-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
CYCLOBENZAPRINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
CYCLOBENZAPRINE HYDROCHLORIDE [VANDF]
Common Name English
NSC-169900
Code English
CYCLOBENZAPRINE HYDROCHLORIDE [USP-RS]
Common Name English
N,N-DIMETHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-(SUP .DELTA.5,.GAMMA.)-PROPYLAMINE HYDROCHLORIDE
Common Name English
CYCLOBENZAPRINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
CYCLOBENZAPRINE HCL
Common Name English
CYCLOBENZAPRINE HYDROCHLORIDE [MART.]
Common Name English
AMRIX
Brand Name English
NSC-173379
Code English
CYCLOBENZAPRINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
CYCLOBENZAPRINE HYDROCHLORIDE [MI]
Common Name English
Cyclobenzaprine hydrochloride [WHO-DD]
Common Name English
CYCLOBENZAPRINE HYDROCHLORIDE [USAN]
Common Name English
NSC-78206
Code English
FLEXERIL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
NCI_THESAURUS C265
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
Code System Code Type Description
PUBCHEM
22576
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
EVMPD
SUB13514MIG
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL669
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
MERCK INDEX
M3976
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1154503
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
SMS_ID
100000079509
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
DAILYMED
0VE05JYS2P
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
FDA UNII
0VE05JYS2P
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
NSC
169900
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
CAS
6202-23-9
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID2045105
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
DRUG BANK
DBSALT000479
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
228-264-4
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
NSC
173379
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
NCI_THESAURUS
C47465
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
NSC
78206
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
CHEBI
3997
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY
RXCUI
52101
Created by admin on Wed Jul 05 23:01:55 UTC 2023 , Edited by admin on Wed Jul 05 23:01:55 UTC 2023
PRIMARY RxNorm
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ACTIVE MOIETY