FRCA Notes


Tramadol and Tapentadol


  • Tramadol is a cyclohexanol derivative
  • Tapentadol is an acyclic (open-chain) phenylpropan-3-amine
  • Both are centrally acting bifunctional ligands, providing analgesia by acting at both opioid and non-opiod receptor sites:
    • Classical opioud receptor agonism
    • Catecholamine reuptake inhibition
Tramadol chemical structure

Presentation

  • Tramadol presents as a racemic mixture of R-tramadol and S-tramadol
    • R-tramadol has MOP receptor affinity 20x that of S-tramadol

  • For oral use: tablets, capsules or sachets (50-400mg SR)
  • For IV/IM use: a solution of 100mg in 2ml

Mechanism of action

  • Tramadol has agonist properties at MOP, KOP and DOP, particularly MOP
  • Potency is 10-20% that of morphine's

  • Its main analgesic activity is through its inhibition of serotonin and noradrenaline re-uptake
  • This promotes activity in descending pathways which inhibit pain transmission

  • Acts at other sites via:
    • NMDA antagonism
    • Nicotinic/muscarinic acetylcholine receptor antagonism
    • Stimulation of pre-synaptic serotonin release

Pharmacodynamics

  • Overall similar effect to morphine
  • Produces less respiratory depression and constipation than morphine at equi-analgesic doses
  • Interacts with TCAs and SSRIs as they will also inhibit central noradrenaline and 5-HT re-uptake
  • Central neurotrasnmitter re-uptake inhibition can cause seizures and therefore shouldn't be used in those with epilepsy

Pharmacokinetics

  • Oral bioavailability 70% (and this may increase to 90% with repeated doses)

  • Distribution
    • Volume of distribution 4L/kg
    • Elimination half life 5-6hrs

  • Metabolism in the liver by CYP2B6, CYP2D6 and CYP3A4 enzymes
  • Subsequent glucuronidation to a number of metabolites
  • Metabolites excreted in the urine

  • Enantiopure preparation which has higher MOP affinity than tramadol and does not require metabolism
  • Effective for acute and possibly also chronic pain symptoms
  • Dose 50mg 4-6hrly

Mechanism of action

  1. MOP receptor agonism
  2. Noradrenaline re-uptake inhibition

Pharmacokinetics

  • Bioavailability 30%
  • Plasma protein binding 20%
  • Elimination half life 4hrs
  • Conjugated in the liver
  • Predominantly renal excretion