Identification

Name
Dexmethylphenidate
Accession Number
DB06701
Type
Small Molecule
Groups
Approved
Description

Dexmethylphenidate is the dextrorotary form of methylphenidate. It is a norepinephrine-dopamine reuptake inhibitor (NDRI) and thus a psychostimulant. It is used for treatment of Attention Deficit Hyperactivity Disorder (ADHD).

Structure
Thumb
Synonyms
  • d-threo-methylphenidate
  • D-TMP
  • Dexmethylphenidate
Product Ingredients
IngredientUNIICASInChI Key
Dexmethylphenidate hydrochloride1678OK0E0819262-68-1JUMYIBMBTDDLNG-OJERSXHUSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dexmethylphenidate HydrochlorideTablet5 mg/1OralSandoz2015-04-27Not applicableUs
Dexmethylphenidate HydrochlorideTablet10 mg/1OralSandoz2015-04-27Not applicableUs
Dexmethylphenidate HydrochlorideTablet2.5 mg/1OralSandoz2015-04-27Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release20 mg/1OralAvera Mc Kennan Hospital2015-12-01Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release30 mg/1OralSandoz2014-01-02Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release5 mg/1OralSandoz2014-11-12Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release20 mg/1OralSandoz2015-06-22Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release10 mg/1OralSandoz2015-02-03Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release25 mg/1OralSandoz2017-01-05Not applicableUs
Dexmethylphenidate Hydrochloride Extended-ReleaseCapsule, extended release40 mg/1OralSandoz2014-03-04Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dexmethylphenidate HydrochlorideTablet5 mg/1OralGavis Pharmaceuticals, LLC.2015-12-04Not applicableUs
Dexmethylphenidate HydrochlorideCapsule, extended release25 mg/1OralPar Pharmaceutical2017-01-05Not applicableUs
Dexmethylphenidate HydrochlorideCapsule, extended release40 mg/1OralTeva2013-11-21Not applicableUs00093 5562 01 nlmimage10 b241d90e
Dexmethylphenidate hydrochlorideCapsule, extended release15 mg/1OralImpax Generics2014-11-11Not applicableUs
Dexmethylphenidate HydrochlorideCapsule, extended release5 mg/1OralPar Pharmaceutical2017-01-05Not applicableUs
Dexmethylphenidate HydrochlorideCapsule, extended release5 mg/1OralActavis Pharma Company2015-08-062017-10-28Us
Dexmethylphenidate HydrochlorideCapsule, extended release10 mg/1OralTeva2015-02-02Not applicableUs00093 5551 01 nlmimage10 ca42e527
Dexmethylphenidate HydrochlorideTablet5 mg/1OralKvk Tech,Inc2015-12-04Not applicableUs
Dexmethylphenidate HydrochlorideCapsule, extended release20 mg/1OralActavis Pharma Company2015-12-212017-09-28Us
Dexmethylphenidate HydrochlorideCapsule, extended release30 mg/1OralTeva2014-05-22Not applicableUs00093 5554 01 nlmimage10 ce42e767
International/Other Brands
Attenade (Celgene)
Categories
UNII
M32RH9MFGP
CAS number
40431-64-9
Weight
Average: 233.3062
Monoisotopic: 233.141578857
Chemical Formula
C14H19NO2
InChI Key
DUGOZIWVEXMGBE-CHWSQXEVSA-N
InChI
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
IUPAC Name
methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate
SMILES
COC(=O)[[email protected]@H]([[email protected]]1CCCCN1)C1=CC=CC=C1

Pharmacology

Indication

Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment.

Structured Indications
Pharmacodynamics

Methylphenidate is a central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy.

Mechanism of action

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.

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Human
ASodium-dependent noradrenaline transporter
inhibitor
Human
USodium-dependent serotonin transporter
inhibitor
Human
Absorption

11-52%

Volume of distribution
Not Available
Protein binding

30%

Metabolism

epatic, methylphenidate is metabolized primarily by de-esterification to ritalinic acid (α-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.

Route of elimination

Renal

Half life

2-4 hours

Clearance
Not Available
Toxicity

Insomnia, dizziness, nausea, stomach pain, euphoria, headache, anxiety, anorexia, and weight loss are common side effects. Symptoms of overdose include vomiting, agitation, tremors, hyperreflexia, muscle twitching, convulsions (may be followed by coma), euphoria, confusion, hallucinations, delirium, sweating, flushing, headache, hyperpyrexia, tachycardia, palpitations, cardiac arrhythmias, hypertension, mydriasis, and dryness of mucous membranes. LD50=190mg/kg (orally in mice)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Dexmethylphenidate.Experimental
AbirateroneThe serum concentration of Dexmethylphenidate can be increased when it is combined with Abiraterone.Approved
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Dexmethylphenidate.Approved
AlgeldrateAlgeldrate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Experimental
AlmagateAlmagate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
AlmasilateAlmasilate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Experimental
AloglutamolAloglutamol can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
AluminiumAluminium can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
Aluminium acetoacetateAluminium acetoacetate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
Aluminium glycinateAluminium glycinate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
Aluminum hydroxideAluminum hydroxide can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
AmineptineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Amineptine.Illicit, Withdrawn
AmiodaroneThe metabolism of Dexmethylphenidate can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Amitriptyline.Approved
ArtemetherThe metabolism of Dexmethylphenidate can be decreased when combined with Artemether.Approved
AsenapineAsenapine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
AtomoxetineThe metabolism of Dexmethylphenidate can be decreased when combined with Atomoxetine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
BetaxololThe metabolism of Dexmethylphenidate can be decreased when combined with Betaxolol.Approved
Bismuth SubcitrateBismuth Subcitrate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
Bismuth subnitrateBismuth subnitrate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
BrofaromineBrofaromine may increase the hypertensive activities of Dexmethylphenidate.Experimental
BupropionThe metabolism of Dexmethylphenidate can be decreased when combined with Bupropion.Approved
Calcium CarbonateCalcium Carbonate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
Calcium silicateCalcium silicate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
CaroxazoneCaroxazone may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
CelecoxibThe metabolism of Dexmethylphenidate can be decreased when combined with Celecoxib.Approved, Investigational
ChloroquineThe metabolism of Dexmethylphenidate can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Dexmethylphenidate can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Dexmethylphenidate can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineCimetidine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
CinacalcetThe metabolism of Dexmethylphenidate can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Dexmethylphenidate can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Dexmethylphenidate can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Dexmethylphenidate can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Clomipramine.Approved, Vet Approved
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Dexmethylphenidate.Experimental
ClotrimazoleThe metabolism of Dexmethylphenidate can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Dexmethylphenidate can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Dexmethylphenidate can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Dexmethylphenidate can be decreased when combined with Cocaine.Approved, Illicit
CyclobenzaprineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Cyclobenzaprine.Approved
DarifenacinThe metabolism of Dexmethylphenidate can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Dexmethylphenidate can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Dexmethylphenidate can be decreased when combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Desipramine.Approved
DexlansoprazoleDexlansoprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
DexrabeprazoleDexrabeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
DibenzepinThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Dibenzepin.Experimental
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Dexmethylphenidate.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Dexmethylphenidate.Experimental
DiphenhydramineThe metabolism of Dexmethylphenidate can be decreased when combined with Diphenhydramine.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Dosulepin.Approved
DoxepinThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Doxepin.Approved
DronedaroneThe metabolism of Dexmethylphenidate can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Dexmethylphenidate can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Dexmethylphenidate can be decreased when combined with Eliglustat.Approved
EpinastineEpinastine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
EsmirtazapineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Esmirtazapine.Investigational
EsomeprazoleEsomeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Dexmethylphenidate.Withdrawn
FamotidineFamotidine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Dexmethylphenidate.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Dexmethylphenidate.Investigational
FluoxetineThe metabolism of Dexmethylphenidate can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Dexmethylphenidate can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Dexmethylphenidate.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Dexmethylphenidate.Approved, Investigational, Vet Approved
HaloperidolThe metabolism of Dexmethylphenidate can be decreased when combined with Haloperidol.Approved
HarmalineHarmaline may increase the hypertensive activities of Dexmethylphenidate.Experimental
HydracarbazineHydracarbazine may increase the hypertensive activities of Dexmethylphenidate.Experimental
HydrotalciteHydrotalcite can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental, Investigational
ImipramineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Imipramine.Approved
IndinavirThe metabolism of Dexmethylphenidate can be decreased when combined with Indinavir.Approved
Ioflupane I-123Dexmethylphenidate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IprindoleThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Iprindole.Experimental
IproclozideIproclozide may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Dexmethylphenidate.Approved
IsoniazidThe metabolism of Dexmethylphenidate can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Dexmethylphenidate can be decreased when combined with Ketoconazole.Approved, Investigational
LansoprazoleLansoprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Lofepramine.Experimental
LopinavirThe metabolism of Dexmethylphenidate can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Dexmethylphenidate can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of Dexmethylphenidate can be decreased when combined with Lumefantrine.Approved
MagaldrateMagaldrate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Withdrawn
Magnesium HydroxideMagnesium Hydroxide can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
Magnesium oxideMagnesium oxide can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
Magnesium peroxideMagnesium peroxide can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
Magnesium silicateMagnesium silicate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Experimental
Magnesium TrisilicateMagnesium Trisilicate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
ManidipineThe metabolism of Dexmethylphenidate can be decreased when combined with Manidipine.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
MethadoneThe metabolism of Dexmethylphenidate can be decreased when combined with Methadone.Approved
MethanthelineMethantheline can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
MethotrimeprazineThe metabolism of Dexmethylphenidate can be decreased when combined with Methotrimeprazine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Dexmethylphenidate.Approved, Investigational
MetiamideMetiamide can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Dexmethylphenidate.Approved, Investigational
MidostaurinThe metabolism of Dexmethylphenidate can be decreased when combined with Midostaurin.Approved
MinaprineMinaprine may increase the hypertensive activities of Dexmethylphenidate.Approved
MirabegronThe metabolism of Dexmethylphenidate can be decreased when combined with Mirabegron.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Mirtazapine.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Dexmethylphenidate.Approved
NevirapineThe metabolism of Dexmethylphenidate can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
NicardipineThe metabolism of Dexmethylphenidate can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Dexmethylphenidate can be decreased when combined with Nilotinib.Approved, Investigational
NizatidineNizatidine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
NortriptylineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Nortriptyline.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
OlanzapineOlanzapine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
OmeprazoleOmeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational, Vet Approved
OpipramolThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Opipramol.Investigational
PanobinostatThe serum concentration of Dexmethylphenidate can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazolePantoprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
PargylinePargyline may increase the hypertensive activities of Dexmethylphenidate.Approved
ParoxetineThe metabolism of Dexmethylphenidate can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Dexmethylphenidate can be decreased when it is combined with Peginterferon alfa-2b.Approved
PhenelzinePhenelzine may increase the hypertensive activities of Dexmethylphenidate.Approved
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Dexmethylphenidate.Approved, Investigational
PheniprazinePheniprazine may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Dexmethylphenidate.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Dexmethylphenidate.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Dexmethylphenidate.Approved, Vet Approved
PirlindolePirlindole may increase the hypertensive activities of Dexmethylphenidate.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
PrimidoneThe serum concentration of the active metabolites of Primidone can be increased when Primidone is used in combination with Dexmethylphenidate.Approved, Vet Approved
PromazineThe metabolism of Dexmethylphenidate can be decreased when combined with Promazine.Approved, Vet Approved
PromethazinePromethazine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Protriptyline.Approved
QuinidineThe metabolism of Dexmethylphenidate can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Dexmethylphenidate can be decreased when combined with Quinine.Approved
RabeprazoleRabeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
RanitidineRanitidine can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
RanolazineThe metabolism of Dexmethylphenidate can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypertensive activities of Dexmethylphenidate.Approved
RitonavirThe metabolism of Dexmethylphenidate can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Dexmethylphenidate can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Dexmethylphenidate can be decreased when combined with Ropinirole.Approved, Investigational
Roxatidine acetateRoxatidine acetate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
SafrazineSafrazine may increase the hypertensive activities of Dexmethylphenidate.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Dexmethylphenidate.Approved, Investigational, Vet Approved
SertralineThe metabolism of Dexmethylphenidate can be decreased when combined with Sertraline.Approved
StiripentolThe metabolism of Dexmethylphenidate can be decreased when combined with Stiripentol.Approved
TerbinafineThe metabolism of Dexmethylphenidate can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Dexmethylphenidate.Approved, Withdrawn
TianeptineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Tianeptine.Approved, Investigational
TiclopidineThe metabolism of Dexmethylphenidate can be decreased when combined with Ticlopidine.Approved
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Dexmethylphenidate.Experimental
TipranavirThe metabolism of Dexmethylphenidate can be decreased when combined with Tipranavir.Approved, Investigational
ToloxatoneToloxatone may increase the hypertensive activities of Dexmethylphenidate.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Dexmethylphenidate.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Dexmethylphenidate.Approved
TrimipramineThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Trimipramine.Approved
VenlafaxineThe metabolism of Dexmethylphenidate can be decreased when combined with Venlafaxine.Approved
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Dexmethylphenidate.Approved
ZiprasidoneThe metabolism of Dexmethylphenidate can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol
  • Avoid excessive quantities of coffee or tea (caffeine)
  • Take on empty stomach: 1 hour before or 2 hours after meals

References

Synthesis Reference

Arie Gutman, "Process for the preparation of dexmethylphenidate hydrochloride." U.S. Patent US20040180928, issued September 16, 2004.

US20040180928
General References
Not Available
External Links
Human Metabolome Database
HMDB15647
PubChem Compound
154101
PubChem Substance
99443255
ChemSpider
135807
BindingDB
50062915
ChEBI
51860
ChEMBL
CHEMBL827
PharmGKB
PA10054
Wikipedia
Dexmethylphenidate
ATC Codes
N06BA11 — Dexmethylphenidate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers / Moods Disorders / Substance-Related Disorders1
1CompletedNot AvailableHealthy Volunteers2
1, 2CompletedBasic ScienceDrug Binding to DAT Receptors1
2Active Not RecruitingTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Deficient Emotional Self-Regulation (DESR)1
2CompletedTreatmentNeoplasms / Tiredness1
3CompletedPreventionAdhd1
3CompletedTreatmentAdhd1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Deficient Emotional Self-Regulation (DESR)1
4CompletedTreatmentAttention-Deficit/Hyperactivity Disorder (ADHD)1
4CompletedTreatmentSarcoidosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral15 mg/1
Capsule, extended releaseOral20 mg/1
Capsule, extended releaseOral25 mg/1
Capsule, extended releaseOral30 mg/1
Capsule, extended releaseOral35 mg/1
Capsule, extended releaseOral40 mg/1
Capsule, extended releaseOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5908850No1995-12-042015-12-04Us
US6355656No1995-12-042015-12-04Us
US6528530No1995-12-042015-12-04Us
US6228398No1999-11-012019-11-01Us
US6635284No1995-12-042015-12-04Us
US7431944No1995-12-042015-12-04Us
US5837284No1995-12-042015-12-04Us
US6730325No1999-11-012019-11-01Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.182 mg/mLALOGPS
logP1.47ALOGPS
logP2.25ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.73 m3·mol-1ChemAxon
Polarizability26.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9663
Caco-2 permeable+0.6564
P-glycoprotein substrateSubstrate0.5466
P-glycoprotein inhibitor INon-inhibitor0.7964
P-glycoprotein inhibitor IINon-inhibitor0.9601
Renal organic cation transporterInhibitor0.532
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5985
CYP450 1A2 substrateNon-inhibitor0.592
CYP450 2C9 inhibitorNon-inhibitor0.897
CYP450 2D6 inhibitorNon-inhibitor0.5245
CYP450 2C19 inhibitorNon-inhibitor0.9265
CYP450 3A4 inhibitorNon-inhibitor0.8539
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9328
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9648
BiodegradationNot ready biodegradable0.5759
Rat acute toxicity2.7718 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8466
hERG inhibition (predictor II)Non-inhibitor0.7491
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Piperidines / Benzene and substituted derivatives / Methyl esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aralkylamine / Monocyclic benzene moiety / Piperidine / Benzenoid / Methyl ester / Amino acid or derivatives / Carboxylic acid ester / Carboxylic acid derivative / Secondary aliphatic amine / Monocarboxylic acid or derivatives
show 10 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
methyl phenyl(piperidin-2-yl)acetate (CHEBI:51860)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Markowitz JS, Patrick KS: Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter? J Clin Psychopharmacol. 2008 Jun;28(3 Suppl 2):S54-61. doi: 10.1097/JCP.0b013e3181733560. [PubMed:18480678]
  2. Ding YS, Fowler JS, Volkow ND, Dewey SL, Wang GJ, Logan J, Gatley SJ, Pappas N: Chiral drugs: comparison of the pharmacokinetics of [11C]d-threo and L-threo-methylphenidate in the human and baboon brain. Psychopharmacology (Berl). 1997 May;131(1):71-8. [PubMed:9181638]
  3. Davids E, Zhang K, Tarazi FI, Baldessarini RJ: Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning. Psychopharmacology (Berl). 2002 Feb;160(1):92-8. Epub 2001 Dec 18. [PubMed:11862378]
  4. Volkow ND, Fowler JS, Gatley SJ, Dewey SL, Wang GJ, Logan J, Ding YS, Franceschi D, Gifford A, Morgan A, Pappas N, King P: Comparable changes in synaptic dopamine induced by methylphenidate and by cocaine in the baboon brain. Synapse. 1999 Jan;31(1):59-66. [PubMed:10025684]
  5. Wayment HK, Deutsch H, Schweri MM, Schenk JO: Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists? J Neurochem. 1999 Mar;72(3):1266-74. [PubMed:10037500]
  6. Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. [PubMed:10199939]
  7. Volkow ND, Wang GJ, Fowler JS, Fischman M, Foltin R, Abumrad NN, Gatley SJ, Logan J, Wong C, Gifford A, Ding YS, Hitzemann R, Pappas N: Methylphenidate and cocaine have a similar in vivo potency to block dopamine transporters in the human brain. Life Sci. 1999;65(1):PL7-12. [PubMed:10403500]
  8. Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. [PubMed:10414438]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  10. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  11. Viggiano D, Vallone D, Sadile A: Dysfunctions in dopamine systems and ADHD: evidence from animals and modeling. Neural Plast. 2004;11(1-2):97-114. [PubMed:15303308]
  12. Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. doi: 10.1124/jpet.108.141713. Epub 2008 Aug 12. [PubMed:18698001]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Markowitz JS, Patrick KS: Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter? J Clin Psychopharmacol. 2008 Jun;28(3 Suppl 2):S54-61. doi: 10.1097/JCP.0b013e3181733560. [PubMed:18480678]
  2. Ding YS, Fowler JS, Volkow ND, Dewey SL, Wang GJ, Logan J, Gatley SJ, Pappas N: Chiral drugs: comparison of the pharmacokinetics of [11C]d-threo and L-threo-methylphenidate in the human and baboon brain. Psychopharmacology (Berl). 1997 May;131(1):71-8. [PubMed:9181638]
  3. Davids E, Zhang K, Tarazi FI, Baldessarini RJ: Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning. Psychopharmacology (Berl). 2002 Feb;160(1):92-8. Epub 2001 Dec 18. [PubMed:11862378]
  4. Yang L, Wang YF, Li J, Faraone SV: Association of norepinephrine transporter gene with methylphenidate response. J Am Acad Child Adolesc Psychiatry. 2004 Sep;43(9):1154-8. [PubMed:15322419]
  5. Williard RL, Middaugh LD, Zhu HJ, Patrick KS: Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity. Behav Pharmacol. 2007 Feb;18(1):39-51. [PubMed:17218796]
  6. Chuhan YS, Taukulis HK: Impairment of single-trial memory formation by oral methylphenidate in the rat. Neurobiol Learn Mem. 2006 Mar;85(2):125-31. Epub 2005 Oct 24. [PubMed:16246598]
  7. Gray JD, Punsoni M, Tabori NE, Melton JT, Fanslow V, Ward MJ, Zupan B, Menzer D, Rice J, Drake CT, Romeo RD, Brake WG, Torres-Reveron A, Milner TA: Methylphenidate administration to juvenile rats alters brain areas involved in cognition, motivated behaviors, appetite, and stress. J Neurosci. 2007 Jul 4;27(27):7196-207. [PubMed:17611273]
  8. Sandoval V, Riddle EL, Ugarte YV, Hanson GR, Fleckenstein AE: Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model. J Neurosci. 2001 Feb 15;21(4):1413-9. [PubMed:11160413]
  9. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  10. Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. doi: 10.1124/jpet.108.141713. Epub 2008 Aug 12. [PubMed:18698001]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. [PubMed:10199939]
  2. Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. [PubMed:10414438]
  3. Stehouwer JS, Jarkas N, Zeng F, Voll RJ, Williams L, Owens MJ, Votaw JR, Goodman MM: Synthesis, radiosynthesis, and biological evaluation of carbon-11 labeled 2beta-carbomethoxy-3beta-(3'-((Z)-2-haloethenyl)phenyl)nortropanes: candidate radioligands for in vivo imaging of the serotonin transporter with positron emission tomography. J Med Chem. 2006 Nov 16;49(23):6760-7. [PubMed:17154506]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on May 06, 2010 10:32 / Updated on November 09, 2017 03:54