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
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
DescriptionCurator'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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093870 |
|||
Target ID: CHEMBL340 |
|||
Target ID: CHEMBL3356 |
|||
Target ID: CHEMBL289 |
|||
Target ID: CHEMBL3257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14681337 |
3.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | CYCLOBENZAPRINE HYDROCHLORIDE Approved UseDrug 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 Date5.7300478E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19243711 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
354.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19243711 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19243711 |
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
Dose | Population | Adverse 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 Sources: Page: p.282Slurred speech Sinus tachycardia |
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 Sources: Page: p.283Confusion Drowsiness Agitation Visual hallucinations |
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) Sources: Page: p.1Cardiovascular disorder NOS CNS depression |
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) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6835493
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 | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)