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Topic summary

Tramadol

Tramadol
Clinical dataPronunciation/ˈtræməˌdɒl/ Trade namesTramal, othersAHFS/Drugs.comMonographMedlinePlusa695011License data
Pregnancy
category
  • AU: C
Routes of
administrationBy mouth, intravenous, intramuscular, rectalDrug class
ATC code
Legal statusLegal status
  • AU:S4 (Prescription only)
  • BR:Class A2 (Narcotic drugs)
  • CA: Schedule I
  • NZ: Class C2
  • UK:POM (Prescription only) /Class C
  • US:Schedule IV
  • UN: Unscheduled
  • EU: Rx-only
  • SE: Förteckning III
    In general: Prescription only
Pharmacokinetic dataBioavailability68% (by mouth), 77% (rectal), 100% (IM)Protein binding20%MetabolismLiver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4MetabolitesO-desmethyltramadol
N-desmethyltramadolOnset of action< 1 hour (by mouth)Elimination half-life6.3 ± 1.4 hDuration of action6 hoursExcretionUrine (95%)Identifiers
  • 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.043.912Chemical and physical dataFormulaC16H25NO2Molar mass263.381 g·mol3D model (JSmol)
Melting point180 to 181 °C (356 to 358 °F)
  • CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O
  • InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1
  • Key:TVYLLZQTGLZFBW-ZBFHGGJFSA-N
(verify)

Tramadol, sold under the brand name Tramal among others, is an opioidpain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderate to severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour. It is also available by injection. It is available in combination with paracetamol (acetaminophen).

As is typical of opioids, common side effects include constipation, itchiness, and nausea. Serious side effects may include hallucinations, seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction. A change in dosage may be recommended in those with kidney or liver problems. It is not recommended in those who are at risk of suicide or in those who are pregnant. While not recommended in women who are breastfeeding, those who take a single dose should not generally have to stop breastfeeding. Tramadol is converted in the liver to O-desmethyltramadol (desmetramadol), an opioid with a stronger affinity for the μ-opioid receptor.

Tramadol was patented in 1972 and launched under the brand name Tramal in 1977 by the West German pharmaceutical companyGrünenthal GmbH. In the mid-1990s, it was approved in the United Kingdom and the United States. It is available as a generic medication and marketed under many brand names worldwide. In 2023, it was the 36th most commonly prescribed medication in the United States, with more than 16million prescriptions.

Wikipedia source