Identification
- Summary
Dexmethylphenidate is a norepinephrine-dopamine reuptake inhibitor used in the treatment of ADHD in conjunction with other therapies.
- Brand Names
- Azstarys, Focalin
- Generic Name
- Dexmethylphenidate
- DrugBank Accession Number
- DB06701
- Background
Dexmethylphenidate is the dextrorotary form of methylphenidate introduced in 20022. It is a norepinephrine-dopamine reuptake inhibitor (NDRI) and thus a psychostimulant5. It is used for treatment of Attention Deficit Hyperactivity Disorder (ADHD)Label,2. The d-isomer is thought to have greater effect with fewer side effects than the l-isomer or the racemic mixture2.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Dexmethylphenidate (DB06701)
- Weight
- Average: 233.3062
Monoisotopic: 233.141578857 - Chemical Formula
- C14H19NO2
- Synonyms
- (+)-threo-methylphenidate
- d-threo-methylphenidate
- D-TMP
- Dexmethylphenidate
- Dexméthylphénidate
- Dexmethylphenidatum
- Dexmetilfenidato
- methyl (R)-phenyl[(R)-piperidin-2-yl]acetate
Pharmacology
- Indication
Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment4,Label.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Adhd •••••••••••• ••••••• ••••••• •••••••• ••••••• - Contraindications & Blackbox Warnings
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Dexmethylphenidate is the d-enantiomer of methylphenidateLabel. This enantiomer is more pharmacologically active than the racemic mixture and may block norepinephrine and dopamine reuptake in synapsesLabel.
- Mechanism of action
Methylphenidate inhibits dopamine and norepinephrine reuptake transporters in synapses, especially in the thalamus and striatum5. One study shows no detectable difference in the caudal prefrontal cortex of treated or untreated monkeys, though multiple rat studies show activity on the prefrontal cortex5. Imaging of human brains after administration of methylphenidate shows changes to blood flow of various regions of the brain including the striatum, supplementary motor area, and posterior parietal cortex5.
Target Actions Organism ASodium-dependent dopamine transporter inhibitorHumans ASodium-dependent noradrenaline transporter inhibitorHumans USodium-dependent serotonin transporter inhibitorHumans - Absorption
Taking dexmethylphenidate with or without food does not affect patients in a clinically relevant way4. 90% of an oral dose is absorbedLabel but as a result of hepatic first pass metabolism, oral bioavailability of dexmethylphenidate is 23% compared to l-methylphenidate with an oral bioavailability of 5% 4. Maximum concentration is generally reached in 1-1.5 hoursLabel.
- Volume of distribution
2.65L/kg when administered intravenously4.
- Protein binding
12-15% of dexmethylphenidate is protein boundLabel. However, other studies have observed 15.2±5.2% protein binding in children and 16.2±1.1% in adults4.
- Metabolism
Dexmethylphenidate is metabolised to the inactive metabolite ritalinic acid by carboxylesterase 1A1 in the liverLabel,1. Other minor pathways metabolise dexmethylphenidate to the inactive metabolites 6-oxo-methylphenidate and p-hydroxy-methylphenidate which are de-esterified and conjugated into other unknown metabolites4.
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- Route of elimination
Dexmethylphenidate is mainly eliminated renally4. After 48 hours, 90% of the dose is collected in the urine and 3.3% is collected from feces4.
- Half-life
The mean terminal half life is approximately 2.2 hoursLabel. However other studies have shown 3.8-3.9 hours3, or 5.96 hours after intravenous administration and 5.69 hours following an oral dose4.
- Clearance
0.40L/hr/kg following an intravenous dose and a renal clearance of 0.005L/hr/kg4,Label.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
There is no difference in effect across genders3,Label. The difference in effect across racial groups, patients under 6 years, renal impairment, hepatic impairment, pregnancy, lactation, and geriatric patients has not been well studied. Patients with renal impairment are not expected to need dose adjustment as the drug is not mainly cleared renallyLabel. Animal studies in pregnant and lactating rats showed delayed fetal skeletal ossification, and reduced weight gain in male offspringLabel. Due to these studies, caution must be exercised and the benefits and risks of taking this drug must be weighedLabel. It is unlikely that dexmethylphenidate is carcinogenic but B6C3F1 mice, which are sensitive to the development of hepatic tumours, developed hepatoblastomas at 2 times the maximum recommended human doseLabel. Methylpheidate was not found to be mutagenic but is weakly clastogenic in Chinese Hamster Ovary cellsLabel. Methylphenidate does not impair fertility in animal studiesLabel.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Dexmethylphenidate is combined with 1,2-Benzodiazepine. Acebutolol Dexmethylphenidate may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Dexmethylphenidate is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Dexmethylphenidate is combined with Acemetacin. Acenocoumarol The serum concentration of the active metabolites of Acenocoumarol can be increased when Acenocoumarol is used in combination with Dexmethylphenidate. - Food Interactions
- Avoid alcohol. Alcohol inhibits the metabolism of dexmethylphenidate.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Dexmethylphenidate hydrochloride 1678OK0E08 19262-68-1 JUMYIBMBTDDLNG-OJERSXHUSA-N - Product Images
- International/Other Brands
- Attenade (Celgene)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Focalin Tablet 10 mg/1 Oral Novartis Pharmaceuticals Corporation 2001-11-30 Not applicable US 
Focalin Tablet 5 mg/1 Oral Novartis Pharmaceuticals Corporation 2001-11-30 Not applicable US Focalin Tablet 2.5 mg/1 Oral Novartis Pharmaceuticals Corporation 2001-11-30 Not applicable US Focalin XR Capsule, extended release 20 mg/1 Oral Novartis Pharmaceuticals Corporation 2005-05-31 Not applicable US Focalin XR Capsule, extended release 15 mg/1 Oral Novartis Pharmaceuticals Corporation 2005-05-31 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dexmethylphenidate HCl Capsule 40 mg/1 Oral Adare Pharmaceuticals Inc 2018-11-01 Not applicable US Dexmethylphenidate HCl Capsule 25 mg/1 Oral Adare Pharmaceuticals Inc 2018-11-01 Not applicable US Dexmethylphenidate HCl Capsule 10 mg/1 Oral Adare Pharmaceuticals Inc 2018-11-01 Not applicable US Dexmethylphenidate HCl Capsule 35 mg/1 Oral Adare Pharmaceuticals Inc 2018-11-01 Not applicable US Dexmethylphenidate HCl Capsule 20 mg/1 Oral Adare Pharmaceuticals Inc 2018-11-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Azstarys Dexmethylphenidate hydrochloride (7.8 mg/1) + Serdexmethylphenidate chloride (39.2 mg/1) Capsule Oral Corium, LLC. 2021-07-16 Not applicable US Azstarys Dexmethylphenidate hydrochloride (5.2 mg/1) + Serdexmethylphenidate chloride (26.1 mg/1) Capsule Oral Corium, LLC. 2021-07-16 Not applicable US Azstarys Dexmethylphenidate hydrochloride (10.4 mg/1) + Serdexmethylphenidate chloride (52.3 mg/1) Capsule Oral Corium, LLC. 2021-07-16 Not applicable US
Categories
- ATC Codes
- N06BA11 — Dexmethylphenidate
- N06BA — Centrally acting sympathomimetics
- N06B — PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS
- N06 — PSYCHOANALEPTICS
- N — NERVOUS SYSTEM
- Drug Categories
- Agents that produce hypertension
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Central Nervous System Stimulants
- Central Nervous System Stimulation
- Centrally Acting Sympathomimetics
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Dopamine Agents
- Dopamine Uptake Inhibitors
- Membrane Transport Modulators
- Methylphenidate and isomer
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Phenylacetates
- Piperidines
- Psychoanaleptics
- Psychostimulants, Agents Used for ADHD and Nootropics
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Chemical TaxonomyProvided by Classyfire
- 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
- Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Methyl ester show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- methyl phenyl(piperidin-2-yl)acetate (CHEBI:51860)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- M32RH9MFGP
- CAS number
- 40431-64-9
- 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
- [H][C@@](C(=O)OC)(C1=CC=CC=C1)[C@@]1([H])CCCCN1
References
- Synthesis Reference
Arie Gutman, "Process for the preparation of dexmethylphenidate hydrochloride." U.S. Patent US20040180928, issued September 16, 2004.
US20040180928- General References
- Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, Hurley TD, Bosron WF: Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther. 2004 Aug;310(2):469-76. doi: 10.1124/jpet.104.067116. Epub 2004 Apr 13. [Article]
- Liu F, Minami H, Silva RR: Dexmethylphenidate hydrochloride in the treatment of attention deficit hyperactivity disorder. Neuropsychiatr Dis Treat. 2006 Dec;2(4):467-73. [Article]
- Modi NB, Wang B, Noveck RJ, Gupta SK: Dose-proportional and stereospecific pharmacokinetics of methylphenidate delivered using an osmotic, controlled-release oral delivery system. J Clin Pharmacol. 2000 Oct;40(10):1141-9. [Article]
- Kimko HC, Cross JT, Abernethy DR: Pharmacokinetics and clinical effectiveness of methylphenidate. Clin Pharmacokinet. 1999 Dec;37(6):457-70. doi: 10.2165/00003088-199937060-00002. [Article]
- Tremblay S, Pieper F, Sachs A, Joober R, Martinez-Trujillo J: The Effects of Methylphenidate (Ritalin) on the Neurophysiology of the Monkey Caudal Prefrontal Cortex. eNeuro. 2019 Mar 4;6(1). pii: eN-NWR-0371-18. doi: 10.1523/ENEURO.0371-18.2018. eCollection 2019 Jan-Feb. [Article]
- Focalin (Dexmethylphenidate) FDA Label [File]
- Dexmethylphenidate XR FDA Label [File]
- External Links
- Human Metabolome Database
- HMDB0015647
- PubChem Compound
- 154101
- PubChem Substance
- 99443255
- ChemSpider
- 135807
- BindingDB
- 50062915
- 352372
- ChEBI
- 51860
- ChEMBL
- CHEMBL827
- ZINC
- ZINC000000896711
- PharmGKB
- PA10054
- Wikipedia
- Dexmethylphenidate
- FDA label
- Download (1.11 MB)
- MSDS
- Download (242 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD) 2 4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD) / Deficient Emotional Self-Regulation (DESR) 1 4 Completed Treatment Sarcoidosis 1 4 Recruiting Treatment Adult Attention Deficit Hyperactivity Disorder (ADHD) 1 4 Recruiting Treatment Attention Deficit Hyperactivity Disorder (ADHD) 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 10 mg Tablet Oral 2.5 mg Tablet Oral 5 mg Capsule Oral Capsule Oral 10 mg/1 Capsule Oral 15 mg/1 Capsule Oral 20 mg/1 Capsule Oral 25 mg/1 Capsule Oral 30 mg/1 Capsule Oral 35 mg/1 Capsule Oral 40 mg/1 Capsule Oral 5 mg/1 Capsule, extended release Oral 25 mg/1 Capsule, extended release Oral 30 mg/1 Capsule, extended release Oral 35 mg/1 Tablet Oral 10 mg/1 Tablet Oral 2.5 mg/1 Tablet Oral 5 mg/1 Capsule, extended release Oral 15 mg/1 Capsule, extended release Oral 40 mg/1 Capsule, extended release Oral 10 mg/1 Capsule, extended release Oral 20 mg/1 Capsule, extended release Oral 5 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5908850 No 1999-06-01 2015-12-04 US US6355656 No 2002-03-12 2015-12-04 US US6528530 No 2003-03-04 2015-12-04 US US6228398 No 2001-05-08 2019-11-01 US US6635284 No 2003-10-21 2015-12-04 US US7431944 No 2008-10-07 2015-12-04 US US5837284 No 1998-11-17 2015-12-04 US US6730325 No 2004-05-04 2019-11-01 US US8062667 No 2011-11-22 2029-03-29 US US8465765 No 2013-06-18 2031-02-15 US US8778390 No 2014-07-15 2031-02-15 US US8563033 No 2013-10-22 2031-02-15 US US8956649 No 2015-02-17 2031-02-15 US US9040083 No 2015-05-26 2031-02-15 US US8287903 No 2012-10-16 2031-02-15 US US7438930 Yes 2008-10-21 2020-06-16 US US9066869 Yes 2015-06-30 2020-06-16 US US7247318 Yes 2007-07-24 2020-06-16 US US7083808 Yes 2006-08-01 2020-06-16 US US6419960 Yes 2002-07-16 2020-06-16 US US8580310 Yes 2013-11-12 2020-06-16 US US9801823 Yes 2017-10-31 2020-06-16 US US10039719 Yes 2018-08-07 2020-06-16 US US9498447 No 2016-11-22 2032-03-23 US US9283214 No 2016-03-15 2032-03-23 US US9023389 No 2015-05-05 2032-03-23 US US8927010 No 2015-01-06 2032-03-23 US US9028868 No 2015-05-12 2032-03-23 US US9034902 No 2015-05-19 2032-03-23 US US9603809 No 2017-03-28 2032-03-23 US US8916588 No 2014-12-23 2032-03-23 US US10182995 No 2019-01-22 2032-03-23 US US10111839 No 2018-10-30 2035-10-30 US US9974752 No 2018-05-22 2035-10-30 US US10292939 No 2019-05-21 2035-10-30 US US10292938 No 2019-05-21 2035-10-30 US US10292937 No 2019-05-21 2032-03-23 US US10449159 No 2019-10-22 2035-10-30 US US10463624 No 2019-11-05 2019-12-16 US US10512613 No 2019-12-24 2035-10-30 US US10500162 No 2019-12-10 2035-10-30 US US10507186 No 2019-12-17 2035-10-30 US US10512612 No 2019-12-24 2035-10-30 US US10568841 No 2020-02-25 2035-10-30 US US10617651 No 2020-04-14 2032-03-23 US US10688060 No 2020-06-23 2035-10-30 US US10722473 No 2020-07-28 2038-11-19 US US10881618 No 2021-01-05 2032-03-23 US US10905652 No 2021-02-02 2032-03-23 US US10858341 No 2020-12-08 2037-12-09 US US10954213 No 2021-03-23 2037-12-09 US US10584112 No 2020-03-10 2037-12-09 US US9079928 No 2015-07-14 2032-07-27 US US10584113 No 2020-03-10 2037-12-09 US US10759778 No 2020-09-01 2037-12-09 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >203 [MSDS] - Predicted Properties
Property Value Source logP 2.25 Chemaxon pKa (Strongest Basic) 9.09 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 38.33 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 66.73 m3·mol-1 Chemaxon Polarizability 26.15 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9941 Blood Brain Barrier + 0.9663 Caco-2 permeable + 0.6564 P-glycoprotein substrate Substrate 0.5466 P-glycoprotein inhibitor I Non-inhibitor 0.7964 P-glycoprotein inhibitor II Non-inhibitor 0.9601 Renal organic cation transporter Inhibitor 0.532 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5985 CYP450 1A2 substrate Non-inhibitor 0.592 CYP450 2C9 inhibitor Non-inhibitor 0.897 CYP450 2D6 inhibitor Non-inhibitor 0.5245 CYP450 2C19 inhibitor Non-inhibitor 0.9265 CYP450 3A4 inhibitor Non-inhibitor 0.8539 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9328 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9648 Biodegradation Not ready biodegradable 0.5759 Rat acute toxicity 2.7718 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8466 hERG inhibition (predictor II) Non-inhibitor 0.7491
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0089-9610000000-8e4c1241e36274356032 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-4190000000-fef041a243a714b6bcaf Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001r-9120000000-b5db236b260a5c8e3151 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0089-3790000000-1d766bcf3e602b1e5a3b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014l-4920000000-775709067ea58a06f13b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-9200000000-bc89321ee3ca13496a53 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9100000000-da8a2bb07df6a5f27f1a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 163.9031387 predictedDarkChem Lite v0.1.0 [M-H]- 154.58199 predictedDeepCCS 1.0 (2019) [M+H]+ 164.2831387 predictedDarkChem Lite v0.1.0 [M+H]+ 156.94 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.1948387 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.03313 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Alcaligenes sp.
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q7SIA5
- Uniprot Name
- Carboxylesterase
- Molecular Weight
- 35647.555 Da
References
- Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, Hurley TD, Bosron WF: Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther. 2004 Aug;310(2):469-76. doi: 10.1124/jpet.104.067116. Epub 2004 Apr 13. [Article]
- Dexmethylphenidate XR FDA Label [File]
Drug created at May 06, 2010 16:32 / Updated at February 02, 2024 22:55