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Methylphenidate

Catalog No. DB00422 Name DrugBank
CAS Number 113-45-1 Website http://www.ualberta.ca/
M. F. C14H19NO2 Telephone (780) 492-3111
M. W. 233.30616 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 305

SYNONYMS

IUPAC name
methyl 2-phenyl-2-(piperidin-2-yl)acetate
IUPAC Traditional name
methylphenidate
Brand Name
Centedrin
Ritalin SR
Metadate CD
PMS-Methylphenidate
Centredin
Methypatch
Metadate
Riphenidate
Ritalin hydrochloride
Ritalin LA
Concerta
Focalin XR
Methylphen
Ritalin-SR
Ritaline
Ritcher Works
Daytrana
Metadate ER
Methylin
Methylin ER
Methylofenidan
Methylphenidan
Plimasine
Ritalin
4311/B Ciba
Calocain
Centedein
Centedrine
Focalin
Meridil
Synonyms
Methylphenidate HCl
Methylphenidatum [INN-Latin]
Methylphenidylacetate hydrochloride
d-methylphenidate HCl
Methyl phenidyl acetate
Methylphenidate hydrochloride
Metilfenidat hydrochloride
Metilfenidato [INN-Spanish]
Metilfenidato [Italian]
Phenidylate
methylphenidate

DATABASE IDS

PubChem SID 46505929
CAS Number 113-45-1
PubChem CID 4158

PROPERTIES

Hydrophobicity(logP) 2.1
Solubility 1255mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved; 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]
Indication For 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.
Pharmacology Methylphenidate is 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.
Toxicity 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
Biotransformation Hepatic, methylphenidate is metabolized primarily by de-esterification to ritalinic acid (α-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.
Absorption Readily absorbed in a biphasic manner. It reaches peak absorption at approximately two hours for the first phase and five hours for the second phase. Bioavailability is low (approximately 30%)
Half Life 2.4 hours in children and 2.1 hours in adults
Protein Binding Low (approximately 15%)
References
Keating GM, McClellan K, Jarvis B: Methylphenidate (OROS formulation). CNS Drugs. 2001;15(6):495-500; discussion 501-3. [Pubmed]
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]
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]
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]
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]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

  • Keating GM, McClellan K, Jarvis B: Methylphenidate (OROS formulation). CNS Drugs. 2001;15(6):495-500; discussion 501-3. Pubmed
  • 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
  • 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
  • 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
  • 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