You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameMethylphenidate
Accession NumberDB00422  (APRD00657)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Its mechanisms appear to be similar to those of dextroamphetamine. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
alpha-Phenyl-2-piperidineacetic acid methyl esterNot AvailableNot Available
DaytranaNot AvailableNot Available
Methyl alpha-phenyl-alpha-(2-piperidyl)acetateNot AvailableNot Available
Methyl alpha-phenyl-alpha-2-piperidinylacetateNot AvailableNot Available
Methyl phenidylacetateNot AvailableNot Available
MethylphenidanNot AvailableNot Available
MethylphenidateNot AvailableNot Available
MethylphenidatumLatinINN
MetilfenidatoItalianINN
MPHNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ritalin LAcapsule, extended release10 mgoralNovartis Pharmaceuticals Corporation2002-06-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ritalintablet5 mgoralNovartis Pharmaceuticals Corporation1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ritalintablet10 mgoralNovartis Pharmaceuticals Corporation1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ritalintablet20 mgoralNovartis Pharmaceuticals Corporation1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet18 mgoralActavis Pharma, Inc.2011-04-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet27 mgoralActavis Pharma, Inc.2011-04-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet36 mgoralActavis Pharma, Inc.2011-04-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet54 mgoralActavis Pharma, Inc.2011-04-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralSandoz Inc1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralSandoz Inc1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralSandoz Inc1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quillivant XRpowder, for suspension300 mg/60mLoralNext Wave Pharmaceuticals, Inc.2012-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quillivant XRpowder, for suspension600 mg/120mLoralNext Wave Pharmaceuticals, Inc.2012-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quillivant XRpowder, for suspension750 mg/150mLoralNext Wave Pharmaceuticals, Inc.2013-01-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quillivant XRpowder, for suspension900 mg/180mLoralNext Wave Pharmaceuticals, Inc.2012-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release18 mgoralJanssen Pharmaceuticals, Inc.2000-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release36 mgoralJanssen Pharmaceuticals, Inc.2000-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release54 mgoralJanssen Pharmaceuticals, Inc.2000-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release27 mgoralJanssen Pharmaceuticals, Inc.2000-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ritalintablet20 mgoralPhysicians Total Care, Inc.2000-03-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release18 mgoralPhysicians Total Care, Inc.2003-03-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release36 mgoralPhysicians Total Care, Inc.2003-03-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release54 mgoralPhysicians Total Care, Inc.2003-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Concertatablet, extended release27 mgoralPhysicians Total Care, Inc.2003-11-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet18 mgoralPhysicians Total Care, Inc.2011-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet27 mgoralPhysicians Total Care, Inc.2011-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylinsolution5 mg/5mLoralShionogi Inc.2010-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylinsolution10 mg/5mLoralShionogi Inc.2010-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet, chewable2.5 mgoralShionogi Inc.2010-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet, chewable5 mgoralShionogi Inc.2010-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet, chewable10 mgoralShionogi Inc.2010-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralbryant ranch prepack1955-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet27 mgoralAmerican Health Packaging2014-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet36 mgoralAmerican Health Packaging2014-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet54 mgoralAmerican Health Packaging2014-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet18 mgoralAmerican Health Packaging2015-01-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Daytranapatch10 mg/9htransdermalNOVEN THERAPEUTICS, LLC2006-04-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Daytranapatch15 mg/9htransdermalNOVEN THERAPEUTICS, LLC2006-04-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Daytranapatch20 mg/9htransdermalNOVEN THERAPEUTICS, LLC2006-04-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Daytranapatch30 mg/9htransdermalNOVEN THERAPEUTICS, LLC2006-04-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methylphenidate Hydrochloridecapsule, extended release20 mgoralTeva Pharmaceuticals USA Inc2012-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release30 mgoralTeva Pharmaceuticals USA Inc2012-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release40 mgoralTeva Pharmaceuticals USA Inc2012-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralMallinckrodt, Inc.2011-03-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralMallinckrodt, Inc.2011-03-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralMallinckrodt, Inc.2011-03-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release10 mgoralMallinckrodt, Inc.2011-03-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release20 mgoralMallinckrodt, Inc.2011-03-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralQualitest Pharmaceuticals2014-09-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralQualitest Pharmaceuticals2014-09-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralQualitest Pharmaceuticals2014-09-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidatetablet5 mgoralSTAT Rx USA LLC1997-08-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release18 mgoralAv Kare, Inc.2014-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release27 mgoralAv Kare, Inc.2014-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release36 mgoralAv Kare, Inc.2014-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release54 mgoralAv Kare, Inc.2014-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralLake Erie Medical DBA Quality Care Products LLC2010-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridesolution5 mg/5mLoralBreckenridge Pharmaceutical, Inc.2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridesolution10 mg/5mLoralBreckenridge Pharmaceutical, Inc.2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralUnither Manufacturing, LLC1977-12-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralUnither Manufacturing, LLC1979-04-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralUnither Manufacturing, LLC1979-04-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidatetablet10 mgoralPhysicians Total Care, Inc.2005-03-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidatetablet5 mgoralPhysicians Total Care, Inc.2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidatetablet20 mgoralPhysicians Total Care, Inc.2007-10-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release20 mgoralPhysicians Total Care, Inc.1994-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralSun Pharmaceutical Industries, Inc.2013-08-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralSun Pharmaceutical Industries, Inc.2013-08-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralSun Pharmaceutical Industries, Inc.2013-08-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridesolution10 mg/5mLoralCaraco Pharmaceutical Laboratories, Ltd.2012-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridesolution5 mg/5mLoralCaraco Pharmaceutical Laboratories, Ltd.2012-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet5 mgoralGolden State Medical Supply2010-05-202015-06-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet10 mgoralGolden State Medical Supply2010-05-202015-06-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylintablet20 mgoralGolden State Medical Supply2010-05-202015-06-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralGolden State Medical Supply, Inc.2010-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralGolden State Medical Supply, Inc.2010-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralGolden State Medical Supply, Inc.2010-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release18 mgoralKremers Urban Pharmaceuticals Inc.2013-07-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release27 mgoralKremers Urban Pharmaceuticals Inc.2013-07-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release36 mgoralKremers Urban Pharmaceuticals Inc.2013-09-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet, extended release54 mgoralKremers Urban Pharmaceuticals Inc.2013-09-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralbryant ranch prepack2010-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralCore Pharma, Llc2014-04-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralCore Pharma, Llc2014-04-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralCore Pharma, Llc2014-04-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralUpstate Pharma, LLC2014-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralUpstate Pharma, LLC2014-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralUpstate Pharma, LLC2014-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release20 mgoralActavis South Atlantic LLC2012-01-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release30 mgoralActavis South Atlantic LLC2012-01-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release40 mgoralActavis South Atlantic LLC2012-01-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet5 mgoralAmerican Health Packaging2014-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet10 mgoralAmerican Health Packaging2014-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridetablet20 mgoralAmerican Health Packaging2014-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Methylphenidate Hydrochloridecapsule, extended release20 mgoralAmerican Health Packaging2014-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
Equasym XLNot Available
Medikinet XLNot Available
MetadateNot Available
QuillivantNot Available
RiphenidateNot Available
Rubifen SRNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methylphenidate Hydrochloride
Thumb
  • InChI Key: JUMYIBMBTDDLNG-UHFFFAOYNA-N
  • Monoisotopic Mass: 269.118256596
  • Average Mass: 269.767
DBSALT000117
Categories
CAS number113-45-1
WeightAverage: 233.3062
Monoisotopic: 233.141578857
Chemical FormulaC14H19NO2
InChI KeyDUGOZIWVEXMGBE-UHFFFAOYSA-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
IUPAC Name
methyl 2-phenyl-2-(piperidin-2-yl)acetate
SMILES
COC(=O)C(C1CCCCN1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Aralkylamine
  • Piperidine
  • Methyl ester
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as an integral part of a total treatment program which typically includes other remedial measures (psychological, educational, social) for a stabilizing effect in children with a behavioral syndrome characterized by the following group of developmentally inappropriate symptoms: moderate-to-severe distractibility, short attention span, hyperactivity, emotional lability, and impulsivity.
PharmacodynamicsMethylphenidate is a central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Methylphenidate also blocks the reuptake of norepinephrine and dopamine. Its mechanisms appear to be similar to those of dextroamphetamine. Furthermore, it is a racemic mixture comprised of the d- and l-threo enantiomers. The d-threo enantiomer is more pharmacologically active than the l-threo enantiomer.
Mechanism of actionMethylphenidate 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. Alteration of serotonergic pathways via changes in dopamine transport may result.
AbsorptionReadily absorbed in a biphasic manner when orally administered (tablets) to children diagnosed with ADHD and to healthy adults. In children and adults males, after administration of a single oral dose of Ritalin LA and Ritalin given in two doses 4 hours apart, peak plasma concentration is reached approximately 2 hours for the first phase and 5-6 hours for the second phase. The absolute oral bioavailability of methylphenidate in children was 22±8% for d-methylphenidate and 5±3% for l-methylphenidate. These low values suggest that methylphenidate is highly metabolized presystemically.
Volume of distribution

d-methylphenidate = 2.65 L/kg;
l-methylphenidate = 1.80 L/kg;

Protein bindingBinding to plasma proteins is low (10%-33%).
Metabolism

Methylphenidate is hepatically metabolized. More specifically, it is rapidly and extensively metabolized by carboxylesterase CES1A1. Via this enzyme, methylphenidate undergoes de-esterification to ritalinic acid (a-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.

Route of eliminationAfter oral administration of an immediate release formulation of methylphenidate, 78%-97% of the dose is excreted in the urine and 1%-3% in the feces in the form of metabolites within 48-96 hours. Only small quantities (<1%) of unchanged methylphenidate appear in the urine. Most of the dose is excreted in the urine as ritalinic acid (60%-86%), the remainder being accounted for by minor metabolites.
Half lifed-methylphenidate = 3-4 hours; l-methylphenidate = 1-3 hours; Ritalinic acid = 3-4 hours;
Clearance

Systemic clearance for Ritalin LA and Ritalin tablets is as follows:
d-methylphenidate= 0.40±0.12 L/h/kg;
l-methylphenidate = 0.73±0.28 L/h/kg;

ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.897
CYP450 2D6 substrateNon-inhibitor0.5245
CYP450 2C19 substrateNon-inhibitor0.9265
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Shire development inc
  • Ucb inc
  • Novartis pharmaceuticals corp
  • Mallinckrodt inc
  • Tris pharma inc
  • Ortho mcneil janssen pharmaceutical inc
  • Able laboratories inc
  • Actavis elizabeth llc
  • Watson laboratories inc
  • Ortho-McNeil-Janssen Pharmaceuticals, Inc.
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseoral10 mg
Capsule, extended releaseoral20 mg
Capsule, extended releaseoral30 mg
Capsule, extended releaseoral40 mg
Patchtransdermal10 mg/9h
Patchtransdermal15 mg/9h
Patchtransdermal20 mg/9h
Patchtransdermal30 mg/9h
Powder, for suspensionoral300 mg/60mL
Powder, for suspensionoral600 mg/120mL
Powder, for suspensionoral750 mg/150mL
Powder, for suspensionoral900 mg/180mL
Solutionoral10 mg/5mL
Solutionoral5 mg/5mL
Tabletoral10 mg
Tabletoral18 mg
Tabletoral20 mg
Tabletoral27 mg
Tabletoral36 mg
Tabletoral5 mg
Tabletoral54 mg
Tablet, chewableoral10 mg
Tablet, chewableoral2.5 mg
Tablet, chewableoral5 mg
Tablet, extended releaseoral10 mg
Tablet, extended releaseoral18 mg
Tablet, extended releaseoral20 mg
Tablet, extended releaseoral27 mg
Tablet, extended releaseoral36 mg
Tablet, extended releaseoral54 mg
Prices
Unit descriptionCostUnit
Daytrana 30 15 mg/9hr Patches Box175.64USD box
Daytrana 30 30 mg/9hr Patches Box174.73USD box
Daytrana 30 10 mg/9hr Patches Box172.78USD box
Daytrana 30 20 mg/9hr Patches Box168.72USD box
Methylphenidate hcl powder44.62USD g
Concerta er 54 mg tablet25.45USD tablet
Concerta er 36 mg tablet23.38USD tablet
Concerta er 27 mg tablet22.65USD tablet
Concerta er 18 mg tablet22.11USD tablet
Metadate cd 50 mg capsule7.08USD capsule
Metadate cd 60 mg capsule7.02USD capsule
Concerta 54 mg Controlled Release Tabs6.18USD tab
Metadate cd 40 mg capsule5.77USD capsule
Concerta 36 mg Controlled Release Tabs5.72USD tab
Focalin xr 30 mg capsule5.42USD capsule
Focalin XR 20 mg 24 Hour Capsule5.31USD capsule
Daytrana 10 mg/9 hr patch5.16USD patch
Daytrana 15 mg/9 hr patch5.16USD patch
Daytrana 20 mg/9 hour patch5.16USD patch
Daytrana 30 mg/9 hour patch5.16USD patch
Focalin xr 15 mg capsule5.16USD capsule
Focalin xr 20 mg capsule5.16USD capsule
Focalin XR 30 mg 24 Hour Capsule5.15USD capsule
Focalin xr 10 mg capsule5.02USD capsule
Concerta 18 mg Controlled Release Tabs5.0USD tab
Concerta 27 mg Controlled Release Tabs5.0USD tab
Focalin XR 10 mg 24 Hour Capsule4.96USD capsule
Focalin xr 5 mg capsule4.95USD capsule
Concerta 54 mg tablet sa4.91USD tablet
Focalin XR 15 mg 24 Hour Capsule4.89USD capsule
Focalin XR 5 mg 24 Hour Capsule4.83USD capsule
Ritalin la 40 mg capsule4.55USD capsule
Concerta 36 mg tablet sa4.51USD tablet
Ritalin la 30 mg capsule4.43USD capsule
Ritalin LA 10 mg 24 Hour Capsule4.42USD capsule
Ritalin LA 20 mg 24 Hour Capsule4.42USD capsule
Ritalin LA 30 mg 24 Hour Capsule4.42USD capsule
Ritalin LA 40 mg 24 Hour Capsule4.42USD capsule
Concerta 27 mg tablet sa4.37USD tablet
Ritalin la 10 mg capsule4.33USD capsule
Ritalin la 20 mg capsule4.33USD capsule
Concerta 18 mg tablet sa4.27USD tablet
Metadate cd 20 mg capsule4.24USD capsule
Metadate cd 30 mg capsule4.24USD capsule
Metadate cd 10 mg capsule4.2USD capsule
Methylphenidate er 10 mg tablet3.24USD tablet
Ritalin SR 20 mg Controlled Release Tabs3.0USD tab
Ritalin sr 20 mg tablet2.67USD tablet
Ritalin 20 mg tablet1.87USD tablet
Focalin 10 mg tablet1.7USD tablet
Ritalin 5 mg tablet1.42USD tablet
Metadate er 20 mg tablet1.32USD tablet
Methylin ER 20 mg Controlled Release Tabs1.3USD tab
Ritalin 10 mg tablet1.29USD tablet
Metadate er 10 mg tablet sa1.28USD tablet
Focalin 5 mg tablet1.26USD tablet
Methylphenidate HCl CR 20 mg Controlled Release Tabs1.2USD tab
Methylin er 20 mg tablet1.12USD tablet
Methylphenidate HCl 20 mg tablet1.05USD tablet
Methylin ER 10 mg1.0USD tab
Methylphenidate HCl 10 mg tablet0.95USD tablet
Methylphenidate HCl 5 mg tablet0.94USD tablet
Methylin er 10 mg tablet0.84USD tablet
Focalin 2.5 mg tablet0.76USD tablet
Methylin 20 mg tablet0.69USD tablet
Methylphenidate 20 mg tablet0.69USD tablet
Ritalin 20 mg Tablet0.67USD tablet
Ritalin Sr 20 mg Extended-Release Tablet0.67USD tablet
Methylin 10 mg tablet0.48USD tablet
Methylphenidate 10 mg tablet0.48USD tablet
Ritalin 10 mg Tablet0.38USD tablet
Apo-Methylphenidate 20 mg Tablet0.37USD tablet
Apo-Methylphenidate Sr 20 mg Extended-Release Tablet0.37USD tablet
Pms-Methylphenidate 20 mg Tablet0.37USD tablet
Sandoz Methylphenidate 20 mg Extended-Release Tablet0.37USD tablet
Methylin 5 mg tablet0.33USD tablet
Methylphenidate 5 mg tablet0.33USD tablet
Apo-Methylphenidate 10 mg Tablet0.17USD tablet
Pms-Methylphenidate 10 mg Tablet0.17USD tablet
Pms-Methylphenidate 5 mg Tablet0.1USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada22648522005-11-012017-09-16
Canada23556442009-01-202019-12-17
United States59584461992-12-122012-12-12
United States76918802004-10-072024-10-07
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point224-226 °CNot Available
water solubility1255mg/LNot Available
logP0.20HANSCH,C ET AL. (1995), pH 7.2
pKa8.77SANGSTER,J (1994)
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
Polarizability26.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.79 KB)
SpectraMS
References
Synthesis Reference

DrugSyn.org

US2512572
General Reference
  1. Keating GM, McClellan K, Jarvis B: Methylphenidate (OROS formulation). CNS Drugs. 2001;15(6):495-500; discussion 501-3. Pubmed
  2. Markowitz JS, DeVane CL, Pestreich LK, Patrick KS, Muniz R: A comprehensive in vitro screening of d-, l-, and dl-threo-methylphenidate: an exploratory study. J Child Adolesc Psychopharmacol. 2006 Dec;16(6):687-98. Pubmed
  3. Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. Pubmed
  4. Sharma RP, Javaid JI, Pandey GN, Easton M, Davis JM: Pharmacological effects of methylphenidate on plasma homovanillic acid and growth hormone. Psychiatry Res. 1990 Apr;32(1):9-17. Pubmed
  5. Shults T, Kownacki AA, Woods WE, Valentine R, Dougherty J, Tobin T: Pharmacokinetics and behavioral effects of methylphenidate in Thoroughbred horses. Am J Vet Res. 1981 May;42(5):722-6. Pubmed
    #FDA label
External Links
ATC CodesN06BA04
AHFS Codes
  • 28:20.92
PDB EntriesNot Available
FDA labelDownload (178 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AliskirenMonitor therapy due to reduced antihypertensive effect of aliskiren.
CarbamazepineCarbamazepine may decrease the effect of methylphendiate.
CyclosporineMethylphenidate increases the effect and toxicity of cyclosporine
GuanethidineMethylphenidate may decrease the effect of guanethidine.
IsocarboxazidPossible hypertensive crisis with this combination
PhenelzinePossible hypertensive crisis with this combination
RasagilinePossible hypertensive crisis with this combination.
TrandolaprilMethylphenidate may antagonize the antihypertensive effect of Trandolapril. Monitor for changes in blood pressure if Methylphenidate is initiated, discontinued or dose changed.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Methylphenidate. Concomitant therapy is contraindicated.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Take on empty stomach: 1 hour before or 2 hours after meals.

Targets

1. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. 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
  8. 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
  9. 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. Epub 2008 Aug 12. Pubmed

2. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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. Epub 2008 Aug 12. Pubmed

3. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

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
  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
  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

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

2. Carboxylesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Carboxylesterase Q6LAP9 Details

References:

  1. FDA label

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24