Methylphenidate: Difference between revisions
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{{Infobox drug | |||
| Watchedfields = changed | |||
| verifiedrevid = 464371569 | |||
| image = Methylphenidate-2D-skeletal.svg | |||
| image_class = skin-invert-image | |||
| width = 200 | |||
| alt = | |||
| caption = | |||
| image2 = Methylphenidate-enantiomers-3D-balls.png | |||
| width2 = 225 | |||
| alt2 = | |||
<!-- Clinical data --> | |||
| pronounce = {{IPAc-en|ˌ|m|ɛ|θ|əl|ˈ|f|ɛ|n|ɪ|d|eɪ|t|,_|-|ˈ|f|iː|-}} | |||
| tradename = Ritalin, Rubifen, Concerta, others | |||
| Drugs.com = {{drugs.com|monograph|methylphenidate-hydrochloride}} | |||
| MedlinePlus = a682188 | |||
| DailyMedID = Methylphenidate | |||
| pregnancy_AU = D | |||
| pregnancy_category = | |||
| dependency_liability = [[Physical dependence|Physical]]: Medium/Moderate<br />[[Psychological dependence|Psychological]]: Medium/Moderate | |||
| addiction_liability = Moderate | |||
| routes_of_administration = [[Oral administration|By mouth]], [[transdermal]], [[insufflation]], [[sublingual]], [[Rectal administration|rectal]], [[intravenous]] | |||
| class = [[Stimulant]]; [[Norepinephrine–dopamine reuptake inhibitor]] (NDRI) | |||
| ATC_prefix = N06 | |||
| ATC_suffix = BA04 | |||
| ATC_supplemental = | |||
<!-- Legal status --> | |||
| legal_AU = S8 | |||
| legal_BR = A3 | |||
| legal_CA = Schedule III | |||
| legal_DE = Anlage III | |||
| legal_NZ = Class B | |||
| legal_UK = Class B | |||
| legal_US = Schedule II | |||
| legal_EU = | |||
| legal_UN = P II | |||
| legal_status = | |||
<!-- Pharmacokinetic data --> | |||
| bioavailability = Insufflation: ~70% | |||
Oral: ~30% (range: 11–52%) | |||
| protein_bound = 10–33% | |||
| metabolism = [[Liver]] (80%) mostly [[CES1]]-mediated | |||
| metabolites = | |||
| onset = | |||
| elimination_half-life = 2–3 hours | |||
| duration_of_action = {{ubl | |||
| Instant-release: 3–4 hours | |||
| Extended-release: 6–12 hours | |||
}} | |||
| excretion = [[Urine]] (90%) | |||
<!-- Identifiers --> | |||
| CAS_number = 20748-11-2 | |||
| PubChem = 4158 | |||
| IUPHAR_ligand = 7236 | |||
| DrugBank = DB00422 | |||
| ChemSpiderID = 4015 | |||
| UNII = 207ZZ9QZ49 | |||
| KEGG = D04999 | |||
| ChEBI = 6887 | |||
| ChEMBL = 796 | |||
| NIAID_ChemDB = | |||
| PDB_ligand = | |||
| synonyms = MPH | |||
<!-- Chemical and physical data --> | |||
| IUPAC_name = Methyl phenyl(piperidin-2-yl)acetate | |||
| C = 14 | |||
| H = 19 | |||
| N = 1 | |||
| O = 2 | |||
| SMILES = COC(=O)C(c1ccccc1)C1CCCCN1 | |||
| StdInChI = 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 | |||
| StdInChIKey = DUGOZIWVEXMGBE-UHFFFAOYSA-N | |||
| density = | |||
| density_notes = | |||
| melting_point = 74 | |||
| melting_high = | |||
| boiling_point = 136 | |||
| solubility = | |||
| sol_units = | |||
| specific_rotation = | |||
}} | |||
<!--T:1--> | <!--T:1--> | ||
==Introduction== | ==Introduction== | ||
Latest revision as of 15:23, 13 January 2025
| Methylphenidate | |
|---|---|
| |
| INN | |
| Drug class | Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI) |
| Routes of administration | By mouth, transdermal, insufflation, sublingual, rectal, intravenous |
| Pregnancy category | |
| Bioavailability | Insufflation: ~70%
Oral: ~30% (range: 11–52%) |
| Metabolism | Liver (80%) mostly CES1-mediated |
| Elimination half-life | 2–3 hours |
| Excretion | Urine (90%) |
| Legal status | |
| CAS Number | 20748-11-2 |
| PubChem | 4158 |
| DrugBank | DB00422 |
| ChemSpider | 4015 |
| KEGG | D04999 |
Introduction[edit]
Methylphenidate is a central nervous system stimulant used for the therapy of attention deficit disorder and narcolepsy.
Liver safety[edit]
Methylphenidate has been linked to a low rate of serum aminotransferase elevations during therapy and to rare instances of acute, clinically apparent liver injury, generally after its intravenous abuse.
Mechanism of action[edit]
Methylphenidate (meth" il fen' i date) is a piperidine derivative that is structurally related to amphetamine which acts as a central nervous system (CNS) sympathomimetic stimulant, probably by causing release of norepinephrine at CNS nerve terminals promoting neurotransmission. Methylphenidate may also affect dopaminergic neurotransmission. Therapy with methylphenidate has been shown to increase cognitive abilities and improve psychological functioning and performance in children and adults with suspected attention deficit disorders. It has a paradoxical calming action in children with hyperactivity. Methylphenidate is also used in the therapy of narcolepsy.
FDA approval information for Methylphenidate[edit]
Methylphenidate was initially approved for use in the United States in 1955 and its indications have been broadened to include children above the age of 6 and adolescents with attention deficit disorder. Methylphenidate is available in multiple forms for oral administration including capsules, tablets, oral solutions and as extended release and long acting forms in concentrations varying from 2.5 to 54 mg in generic forms and under several brand names including Ritalin, Concerta and Metadate. Transdermal formulations are also available.
Dosage and administration for Methylphenidate[edit]
The usual dose in adults is 10 mg two or three times daily and average maintenance dosage is 40 to 60 mg daily. The dosage in children varies by formulation. Methylphenidate is a controlled substance (Schedule II) and has abuse potential.
Side effects of Methylphenidate[edit]
Common side effects include headache, insomnia, irritability, palpitations, tachycardia, nasal stuffiness, decreased appetite, cough and rash.
The following are CNS stimulants
- Amphetamines (including ecstasy or methylenedioxymetamphetamine)
- Armodafinil
- Atomoxetine
- Cocaine
- Methylphenidate
- Modafinil
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