Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H21N |
| Molecular Weight | 275.3874 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C13
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
| 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 |
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 |
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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 |
|---|---|---|---|---|
| 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 Date1988 |
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 |
healthy, 18 |
Disc. AE: Lethargy, Slurred speech... AEs leading to discontinuation/dose reduction: Lethargy Sources: Slurred speech Sinus tachycardia |
600 mg single, oral Overdose |
healthy, 24 |
Disc. AE: Sinus tachycardia, Confusion... AEs leading to discontinuation/dose reduction: Sinus tachycardia Sources: Confusion 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: |
unhealthy, 41.5 |
Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence (5.2%) Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Serotonin syndrome, Cardiovascular disorder NOS... AEs leading to discontinuation/dose reduction: Serotonin syndrome (grade 4) Sources: Cardiovascular 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 |
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 |
healthy, 18 |
| Sinus tachycardia | Disc. AE | 900 mg single, oral Overdose |
healthy, 18 |
| Slurred speech | Disc. AE | 900 mg single, oral Overdose |
healthy, 18 |
| Agitation | Disc. AE | 600 mg single, oral Overdose |
healthy, 24 |
| Confusion | Disc. AE | 600 mg single, oral Overdose |
healthy, 24 |
| Drowsiness | Disc. AE | 600 mg single, oral Overdose |
healthy, 24 |
| Sinus tachycardia | Disc. AE | 600 mg single, oral Overdose |
healthy, 24 |
| Visual hallucinations | Disc. AE | 600 mg single, oral Overdose |
healthy, 24 |
| 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: |
unhealthy, 41.5 |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetic profile of once-daily cyclobenzaprine extended-release. | 2010-11 |
|
| Efficacy and tolerability of cyclobenzaprine extended release for acute muscle spasm: a pooled analysis. | 2010-07 |
|
| Evidence that tricyclic small molecules may possess toll-like receptor and myeloid differentiation protein 2 activity. | 2010-06-30 |
|
| Pharmacologic management of chronic pain. | 2010-06 |
|
| Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010-04-07 |
|
| Menstrual-related nummular headache. | 2010-04 |
|
| Case files of the California poison control system, San Francisco division: blue thunder ingestion: methanol, nitromethane, and elevated creatinine. | 2010-03 |
|
| Antidepressant drugs in oral fluid using liquid chromatography-tandem mass spectrometry. | 2010-03 |
|
| Impact of poor-quality medicines in the 'developing' world. | 2010-03 |
|
| Comparison of ibuprofen, cyclobenzaprine or both in patients with acute cervical strain: a randomized controlled trial. | 2010-01 |
|
| A 19-month-old girl with recurrent illness: over the hills and through the woods. | 2009-12 |
|
| Patients' experiences of living with and receiving treatment for fibromyalgia syndrome: a qualitative study. | 2009-10-07 |
|
| Electroencephalographic correlates of Chronic Fatigue Syndrome. | 2009-10-06 |
|
| Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009-10-02 |
|
| Fibromyalgia and myofascial pain syndrome-a dilemma. | 2009-10 |
|
| Plasmapheresis in a patient with rhabdomyolysis: a case report. | 2009-08-12 |
|
| Methemoglobinemia: life-threatening hazard of multiple drug ingestions. | 2009-07-18 |
|
| Cyclobenzaprine for the treatment of myofascial pain in adults. | 2009-07-08 |
|
| Standardized natural product cannabis in pain management and observations at a Canadian compassion society: a case report. | 2009-05-18 |
|
| Is there sufficient evidence to suggest cyclobenzaprine might be implicated in causing serotonin toxicity? | 2009-05 |
|
| Cyclobenzaprine ER for muscle spasm associated with low back and neck pain: two randomized, double-blind, placebo-controlled studies of identical design. | 2009-05 |
|
| Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine. | 2009-04-28 |
|
| Bioavailability of a controlled-release cyclobenzaprine tablet and influence of a high fat meal on bioavailability. | 2009-04 |
|
| Rhabdomyolysis associated with the nutritional supplement Hydroxycut. | 2009-01-15 |
|
| A pharmacokinetic comparison of single doses of once-daily cyclobenzaprine extended-release 15 mg and 30 mg: a randomized, double-blind, two-period crossover study in healthy volunteers. | 2009-01 |
|
| Insights in to the pathogenesis of axial spondyloarthropathy based on gene expression profiles. | 2009 |
|
| Torticollis under cyclobenzaprine. | 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 |
|
| 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 |
|
| Treatment options and patient perspectives in the management of fibromyalgia: future trends. | 2008-12 |
|
| Newer treatments for fibromyalgia syndrome. | 2008-12 |
|
| Anticholinergic esotropia. | 2008-12 |
|
| A six-month double-blind, placebo-controlled, randomized clinical trial of duloxetine for the treatment of fibromyalgia. | 2008-11-30 |
|
| Elderly patient refractory to multiple pain medications successfully treated with integrative East-West medicine. | 2008-11-30 |
|
| Bertolotti's syndrome: a case report. | 2008-11-29 |
|
| Leiomyosarcoma of the breast in a patient with a 10-year-history of cyclophosphamide exposure: a case report. | 2008-11-07 |
|
| Lower facial contouring with botulinum toxin type A. | 2008-11 |
|
| Serotonin syndrome in a patient taking Lexapro and Flexeril: a case report. | 2008-11 |
|
| Pharmacotherapy of chronic pain: a synthesis of recommendations from systematic reviews. | 2008-10-25 |
|
| Neuralgic amyotrophy associated with antibiotic therapy. | 2008-09 |
|
| Choosing a skeletal muscle relaxant. | 2008-08-01 |
|
| Rasagiline in treatment of Parkinson's disease. | 2008-02 |
|
| Skeletal muscle relaxants. | 2008-02 |
|
| Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | 2008 |
|
| 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 |
|
| Cost-utility of an 8-month aquatic training for women with fibromyalgia: a randomized controlled trial. | 2008 |
|
| Extended-release cyclobenzaprine (Amrix). | 2007-12-17 |
|
| Antidepressants in the treatment of fibromyalgia. | 2006-12 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 07:35:22 GMT 2025
by
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on
Wed Apr 02 07:35:22 GMT 2025
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| Record UNII |
69O5WQQ5TI
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| Record Status |
Validated (UNII)
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| Record Version |
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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 |
NBK548894
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WHO-ATC |
M03BX08
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Cyclobenzaprine
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SUB06849MIG
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69O5WQQ5TI
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751
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CYCLOBENZAPRINE
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206-145-8
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CHEMBL669
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m3976
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7152
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100000083730
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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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3996
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69O5WQQ5TI
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21949
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2895
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DTXSID0046933
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Route of Elimination | PHARMACOKINETIC |
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EXCRETED UNCHANGED, RENAL PHARMACOKINETIC |
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| PROTEIN BINDING | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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ORAL, EXTENDED-RELEASE PHARMACOKINETIC PHARMACOKINETIC |
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| ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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ORAL, EXTENDED-RELEASE CAPSULE (15 mg DOSE) PHARMACOKINETIC PHARMACOKINETIC |
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