Methylphenidate and its isomers: their role in the treatment of attention-deficit hyperactivity disorder using a transdermal delivery system

CNS Drugs. 2006;20(9):713-38. doi: 10.2165/00023210-200620090-00002.

Abstract

dl-threo-Methylphenidate is a highly efficacious drug for treating attention-deficit hyperactivity disorder (ADHD) that is currently administered as immediate- or controlled-release and osmotically controlled-released formulations. The drug exists as two enantiomers, d-threo-methylphenidate and l-threo-methylphenidate, with the former having been developed as a medication to treat ADHD in its own right. dl-threo-Methylphenidate undergoes enantioselective metabolism in the liver, which results in marked differences in the plasma concentrations of its isomers, depending on the route of administration and formulation. When dl-threo-methylphenidate is orally administered, the plasma concentrations of d-threo-methylphenidate are higher than those of l-threo-methylphenidate. However, with the recently developed methylphenidate transdermal system (MTS), 'first-pass' metabolism is circumvented and, as a consequence, plasma concentrations of d-threo-methylphenidate are consistent with those produced by oral formulations, but the relative concentrations of l-threo-methylphenidate are much higher, i.e. 50-60% of those of d-threo-methylphenidate. In this article, we review the pharmacokinetics and pharmacology of dl-threo-methylphenidate and its isomers to assess the extent to which their mechanism of action as noradrenaline (norepinephrine) and dopamine reuptake inhibitors is responsible for their efficacy and commonly occurring adverse effects. The major findings are that d-threo-methylphenidate and l-threo-methylphenidate share the same pharmacological profile as the parent racemate, i.e. catecholamine-selective reuptake inhibition with higher potency against dopamine versus noradrenaline reuptake in vivo. However, d-threo-methylphenidate is approximately 10-fold more potent than the l-isomer in this regard. For these drugs, their abilities not only to ameliorate the behavioural and cognitive dysfunctions in ADHD, but also to induce the common adverse effects of reduced appetite, nausea/vomiting and stomach ache, are almost certainly due to their ability to potentiate noradrenergic and/or dopaminergic function in the central and peripheral nervous systems. The sympathomimetic actions of ADHD drugs on cardiovascular function are currently an issue of concern. Since noradrenaline reuptake inhibition is the likely mediator for the effects of dl-threo-methylphenidate on blood pressure and heart rate, the more potent d-isomer will therefore be predominantly responsible. Motor and vocal tics are the other important adverse event to be considered in the treatment of ADHD. It is now accepted that tics are a frequently occurring behavioural manifestation of ADHD itself and the evidence for or against their exacerbation by treatment with dl-threo-methylphenidate or other stimulants remains highly contradictory. Focusing on the enantiomers of dl-threo-methylphenidate, it can be concluded that d-threo-methylphenidate, which is the more potent and abundant of the two isomers, is the major contributor of both efficacy and adverse effects, irrespective of the formulation or route of administration of the racemate. Moreover, for the oral, extended-release formulations of dl-threo-methylphenidate, the d-isomer represents the only pharmacologically active moiety when these medications are used in the clinic. With the MTS, plasma concentrations of l-threo-methylphenidate are higher than are achieved using oral formulations, but even in this case, it is likely that the contribution of this enantiomer to the efficacy and adverse effects of the racemate is no greater than 5-10% of the total.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Administration, Cutaneous
  • Animals
  • Attention Deficit Disorder with Hyperactivity / drug therapy*
  • Central Nervous System Stimulants / administration & dosage*
  • Central Nervous System Stimulants / chemistry
  • Central Nervous System Stimulants / pharmacology
  • Drug Delivery Systems*
  • Humans
  • Isomerism
  • Methylphenidate / administration & dosage*
  • Methylphenidate / chemistry
  • Methylphenidate / pharmacology

Substances

  • Central Nervous System Stimulants
  • Methylphenidate