Tramadol

Tramadol
Clinical data
Pronunciation/ˈtræməˌdɒl/
Trade namesUltram, Zytram, Ralivia, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa695011
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous, intramuscular, rectal
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability68% (by mouth),[8] 77% (rectal), 100% (IM)[9]
Protein binding20%[10]
MetabolismLiver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4[9][11]
MetabolitesO-desmethyltramadol
N-desmethyltramadol
Onset of action< 1 hour (by mouth)[10]
Elimination half-life6.3 ± 1.4 h[11]
Duration of action6 hours[12]
ExcretionUrine (95%)[13]
Identifiers
  • 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.912 Edit this at Wikidata
Chemical and physical data
FormulaC16H25NO2
Molar mass263.381 g·mol−1
3D 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 checkY
  • Key:TVYLLZQTGLZFBW-ZBFHGGJFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tramadol, sold under the brand name Ultram among others,[1] is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderately severe pain.[10][14] When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour.[10] It is also available by injection.[15] It is available in combination with paracetamol (acetaminophen).

As is typical of opioids, common side effects include constipation, itchiness, and nausea.[10] Serious side effects may include hallucinations, seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction.[10] A change in dosage may be recommended in those with kidney or liver problems.[10] It is not recommended in those who are at risk of suicide or in those who are pregnant.[10][15] While not recommended in women who are breastfeeding, those who take a single dose should not generally have to stop breastfeeding.[16] Tramadol is converted in the liver to O-desmethyltramadol (desmetramadol), an opioid with a stronger affinity for the μ-opioid receptor.[10][17]

Tramadol was patented in 1972 and launched under the name "Tramal" in 1977 by the West German pharmaceutical company Grünenthal GmbH.[14][18] In the mid-1990s, it was approved in the United Kingdom and the United States.[14] It is available as a generic medication and marketed under many brand names worldwide.[1][10] In 2022, it was the 55th most commonly prescribed medication in the United States, with more than 12 million prescriptions.[19][20]

  1. ^ a b c "Tramadol". Drugs.com. Archived from the original on 23 July 2018. Retrieved 22 December 2018.
  2. ^ "Tramadol Use During Pregnancy". Drugs.com. 14 October 2019. Archived from the original on 13 April 2020. Retrieved 7 February 2020.
  3. ^ Cite error: The named reference MedlinePlus was invoked but never defined (see the help page).
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 3 August 2023.
  5. ^ "Ralivia Product information". Health Canada. 25 April 2012. Archived from the original on 8 May 2021. Retrieved 3 July 2022.
  6. ^ "Ultram- tramadol hydrochloride tablet, coated". DailyMed. 7 June 2022. Archived from the original on 1 December 2021. Retrieved 3 July 2022.
  7. ^ "List of nationally authorized medicinal products" (PDF). European Medicines Agency. 28 January 2021. Archived (PDF) from the original on 15 July 2021. Retrieved 10 April 2024.
  8. ^ Polsten GR, Wallace MS (21 June 2016). "Analgesic Agents in Rheumatic Disease". In Firestein GS, Budd R, Gabriel SE, McInnes IB, O'Dell JR (eds.). Kelley and Firestein's Textbook of Rheumatology. Elsevier Health Sciences. pp. 1081–. ISBN 978-0-323-41494-4.
  9. ^ a b Brayfield, A, ed. (13 December 2013). "Tramadol Hydrochloride". Martindale: The Complete Drug Reference. Pharmaceutical Press. Archived from the original on 29 August 2021. Retrieved 5 April 2014.
  10. ^ a b c d e f g h i j "Tramadol Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 12 November 2020. Retrieved 10 April 2024.
  11. ^ a b "Ultram, Ultram ER (tramadol) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 3 December 2013. Retrieved 10 April 2024.
  12. ^ Dayer P, Desmeules J, Collart L (1997). "[Pharmacology of tramadol]". Drugs. 53 (Suppl 2): 18–24. doi:10.2165/00003495-199700532-00006. PMID 9190321. S2CID 46970093.
  13. ^ "Australian Label: Tramadol Sandoz 50 mg capsules" (PDF). TGA eBusiness Services. 4 November 2011. Archived from the original on 1 August 2016. Retrieved 6 April 2014.
  14. ^ a b c Leppert W (November–December 2009). "Tramadol as an analgesic for mild to moderate cancer pain". Pharmacological Reports. 61 (6): 978–992. doi:10.1016/s1734-1140(09)70159-8. PMID 20081232. S2CID 4731268.
  15. ^ a b British national formulary: BNF 74 (74 ed.). British Medical Association. 2017. pp. 447–448. ISBN 978-0857112989.
  16. ^ "Tramadol Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 13 April 2020. Retrieved 5 September 2016.
  17. ^ Raffa RB, Buschmann H, Christoph T, Eichenbaum G, Englberger W, Flores CM, et al. (July 2012). "Mechanistic and functional differentiation of tapentadol and tramadol". Expert Opinion on Pharmacotherapy. 13 (10): 1437–1449. doi:10.1517/14656566.2012.696097. PMID 22698264. S2CID 24226747.
  18. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 528. ISBN 9783527607495. Archived from the original on 29 August 2021. Retrieved 3 September 2020.
  19. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  20. ^ "Tramadol Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.