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 |
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Target ID: CHEMBL2093870 |
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Target ID: CHEMBL340 |
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Target ID: CHEMBL3356 |
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Target ID: CHEMBL289 |
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Target ID: CHEMBL3257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14681337 |
3.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Hallucinations in an elderly patient taking recommended doses of cyclobenzaprine. | 2000 May 8 |
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Release of cyclobenzaprine hydrochloride from osmotically rupturable tablets. | 2002 Jul |
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The lack of a placebo effect in a trial of fluoxetine in the treatment of fibromyalgia. | 2002 Nov |
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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 |
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Cyclobenzaprine with ibuprofen versus ibuprofen alone in acute myofascial strain: a randomized, double-blind clinical trial. | 2003 Jun |
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Prescription of nonsteroidal anti-inflammatory drugs and muscle relaxants for back pain in the United States. | 2004 Dec 1 |
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Human liver aldehyde oxidase: inhibition by 239 drugs. | 2004 Jan |
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Medicinal and injection therapies for mechanical neck disorders. | 2005 Apr 18 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Low-dose cyclobenzaprine versus combination therapy with ibuprofen for acute neck or back pain with muscle spasm: a randomized trial. | 2005 Sep |
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Persistent low back pain. | 2005 Sep 1 |
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Fatality after deliberate ingestion of sustained-release ibuprofen: a case report. | 2006 |
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Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs. | 2006 Dec |
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Shift work and pathological conditions. | 2006 Dec 11 |
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Rhabdomyolysis: a manifestation of cyclobenzaprine toxicity. | 2006 Jul 17 |
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Extended-release cyclobenzaprine (Amrix). | 2007 Dec 17 |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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Do motor control genes contribute to interindividual variability in decreased movement in patients with pain? | 2007 Jul 26 |
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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 |
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A meta-analysis of the efficacy of fibromyalgia treatment according to level of care. | 2008 |
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Choosing a skeletal muscle relaxant. | 2008 Aug 1 |
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Treatment options and patient perspectives in the management of fibromyalgia: future trends. | 2008 Dec |
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Anticholinergic esotropia. | 2008 Dec |
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Lower facial contouring with botulinum toxin type A. | 2008 Nov |
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Serotonin syndrome in a patient taking Lexapro and Flexeril: a case report. | 2008 Nov |
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Torticollis under cyclobenzaprine. | 2009 |
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Plasmapheresis in a patient with rhabdomyolysis: a case report. | 2009 Aug 12 |
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Is there sufficient evidence to suggest cyclobenzaprine might be implicated in causing serotonin toxicity? | 2009 May |
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Cyclobenzaprine ER for muscle spasm associated with low back and neck pain: two randomized, double-blind, placebo-controlled studies of identical design. | 2009 May |
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Standardized natural product cannabis in pain management and observations at a Canadian compassion society: a case report. | 2009 May 18 |
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Fibromyalgia and myofascial pain syndrome-a dilemma. | 2009 Oct |
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Patients' experiences of living with and receiving treatment for fibromyalgia syndrome: a qualitative study. | 2009 Oct 7 |
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Comparison of ibuprofen, cyclobenzaprine or both in patients with acute cervical strain: a randomized controlled trial. | 2010 Jan |
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Efficacy and tolerability of cyclobenzaprine extended release for acute muscle spasm: a pooled analysis. | 2010 Jul |
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Pharmacologic management of chronic pain. | 2010 Jun |
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Impact of poor-quality medicines in the 'developing' world. | 2010 Mar |
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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
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29696
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NDF-RT |
N0000175737
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NDF-RT |
N0000175730
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WHO-VATC |
QM03BX08
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LIVERTOX |
247
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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
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Code System | Code | Type | Description | ||
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Cyclobenzaprine
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PRIMARY | |||
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SUB06849MIG
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PRIMARY | |||
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69O5WQQ5TI
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PRIMARY | |||
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751
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PRIMARY | |||
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CYCLOBENZAPRINE
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PRIMARY | |||
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206-145-8
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CHEMBL669
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M3976
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PRIMARY | Merck Index | ||
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7152
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DB00924
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303-53-7
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8305
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791
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C004704
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C28947
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21949
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PRIMARY | RxNorm | ||
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2895
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303-53-7
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)