Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H19NO2 |
Molecular Weight | 233.3062 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2
InChI
InChIKey=DUGOZIWVEXMGBE-CHWSQXEVSA-N
InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1
Molecular Formula | C14H19NO2 |
Molecular Weight | 233.3062 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Dexmethylphenidate is the dextrorotary form of methylphenidate. Dexmethylphenidate is marketed under the trade name Focalin. Focalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic
methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threoenantiomers. Focalin is a central nervous system (CNS) stimulant, available in three tablet strengths. Each tablet contains dexmethylphenidate hydrochloride 2.5, 5, or 10 mg for oral administration. Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment. Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
161.0 nM [Ki] | |||
206.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FOCALIN Approved UseFocalin XR is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) in patients aged 6 years and older. The effectiveness of Focalin XR in the treatment of ADHD in patients aged 6 years and older was established in two placebo-controlled studies in patients meeting DSM-IV criteria for ADHD. Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.13 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
23.72 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
131.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
120.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
79.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXMETHYLPHENIDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Vomiting, Agitation... Other AEs: Vomiting Sources: Agitation Tremor Hyperreflexia Muscle twitching Convulsions Euphoria Confusion Hallucinations Delirium Sweating Flushing Headache Hyperpyrexia Tachycardia Palpitations Cardiac arrhythmias Hypertension Mydriasis Mucosal dryness Rhabdomyolysis |
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: Twitching, Anorexia... AEs leading to discontinuation/dose reduction: Twitching (1%) Sources: Anorexia (1%) Insomnia (1%) Tachycardia (1%) Insomnia (1.8%) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Cardiac disorders, Stroke... Other AEs: Increased blood pressure, Heart rate increased... AEs leading to discontinuation/dose reduction: Cardiac disorders (grade 3-5) Other AEs:Stroke (grade 3-5) Myocardial infarction (grade 3-5) Seizures Raynaud's phenomenon Increased blood pressure Sources: Heart rate increased Psychotic symptom (grade 3-5) Psychotic symptom Manic symptom Aggression Growth suppression Priapism Erection prolonged Vascular disorders Visual disturbance |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Feeling jittery, Anorexia... AEs leading to discontinuation/dose reduction: Feeling jittery (1.8%) Sources: Anorexia (1.2%) Anxiety (1.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Agitation | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Cardiac arrhythmias | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Confusion | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Convulsions | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Delirium | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Euphoria | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Flushing | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hallucinations | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Headache | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hyperpyrexia | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hyperreflexia | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hypertension | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Mucosal dryness | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Muscle twitching | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Mydriasis | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Palpitations | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Rhabdomyolysis | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Sweating | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Tachycardia | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Tremor | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Vomiting | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Anorexia | 1% 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: |
Insomnia | 1% 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: |
Tachycardia | 1% 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: |
Twitching | 1% 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: |
Insomnia | 1.8% 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: |
Aggression | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Erection prolonged | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Growth suppression | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Heart rate increased | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Increased blood pressure | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Manic symptom | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Priapism | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Psychotic symptom | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Vascular disorders | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Visual disturbance | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Raynaud's phenomenon | Disc. AE | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Seizures | Disc. AE | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Psychotic symptom | grade 3-5 | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Cardiac disorders | grade 3-5 Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Myocardial infarction | grade 3-5 Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Stroke | grade 3-5 Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Anorexia | 1.2% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Anxiety | 1.2% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Feeling jittery | 1.8% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | no (co-administration study) Comment: Clinically, methylphenidate coadministration did not increase plasma concentrations of the CYP2D6 substrate desipramine. Page: 11.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15082749/ Page: - |
no | |||
Sources: https://www.pharmgkb.org/pmid/16621932 Page: - |
weak | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12215063/ Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Prescribing ritalin in combined modality management of hyperactivity with attention deficit]. | 2001 Sep-Oct |
|
A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects. | 2004 Feb |
|
Efficacy of two once-daily methylphenidate formulations compared across dose levels at different times of the day: preliminary indications from a secondary analysis of the COMACS study data. | 2004 Sep 30 |
|
Evolution of the treatment of attention-deficit/hyperactivity disorder in children: a review. | 2008 May |
|
Psychopharmacology of ADHD in pediatrics: current advances and issues. | 2009 |
|
Once-daily medications for the pharmacological management of ADHD in adults. | 2009 Apr |
|
Long-term effectiveness and safety of dexmethylphenidate extended-release capsules in adult ADHD. | 2009 Mar |
|
Efficacy of dexmethylphenidate for the treatment of fatigue after cancer chemotherapy: a randomized clinical trial. | 2009 Nov |
Patents
Sample Use Guides
Focalin (Dexmethylphenidate) is administered twice daily, at least 4 hours apart. Focalin may be administered with or without food. The recommended starting dose of Focalin for patients who are not currently taking racemic
methylphenidate, or for patients who are on stimulants other than methylphenidate, is 5
mg/day (2.5 mg twice daily).
Dosage may be adjusted in 2.5 to 5 mg increments to a maximum of 20 mg/day (10 mg twice daily). In general, dosage adjustments may proceed at approximately weekly intervals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21129986
Dexmethylphenidate inhibition [3H]dopamine uptake at human DAT expressed in mouse N2A cells with IC50 156 nM.
Substance Class |
Chemical
Created
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admin
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Record UNII |
M32RH9MFGP
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Record Status |
Validated (UNII)
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WHO-VATC |
QN06BA11
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NDF-RT |
N0000175729
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NCI_THESAURUS |
C47795
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WHO-ATC |
N06BA11
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LIVERTOX |
291
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NDF-RT |
N0000175739
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CHEMBL827
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DEXMETHYLPHENIDATE
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m7453
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7554
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BINDER->LIGAND |
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SALT/SOLVATE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Tmax | PHARMACOKINETIC |
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following oral administration of serdexmethylphenidate single moiety alone PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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IN HEALTHY ADULT SUBJECTS PHARMACOKINETIC |
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