Global InformationTramadol information
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| Pronunciation | tra' ma doll |
| Trade names | Ultram, Zytram, Ralivia, others[1] |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a695011 |
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| Dependence liability | Low–moderate[3] |
| Routes of administration | By mouth, intravenous (IV), intramuscular (IM), rectal |
| Drug class | Opioid analgesic[4] |
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| Pharmacokinetic data | |
| Bioavailability | 70–75% (by mouth), 77% (rectal), 100% (IM)[9] |
| Protein binding | 20%[3] |
| Metabolism | Liver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4[9][10] |
| Metabolites | O-desmethyltramadol N-desmethyltramadol |
| Onset of action | Less than 1 hour (by mouth)[3] |
| Elimination half-life | 6.3 ± 1.4 h[10] |
| Duration of action | 6 hours[11] |
| Excretion | Urine (95%)[12] |
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| ECHA InfoCard | 100.043.912 |
| Chemical and physical data | |
| Formula | C16H25NO2 |
| Molar mass | 263.381 g·mol−1 |
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| Melting point | 180 to 181 °C (356 to 358 °F) |
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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.[3][13] When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour.[3] It is also available by injection.[14] It is available in combination with paracetamol (acetaminophen).
As is typical of opioids, common side effects include constipation, itchiness, and nausea.[3] Serious side effects may include hallucinations, seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction.[3] A change in dosage may be recommended in those with kidney or liver problems.[3] It is not recommended in those who are at risk of suicide or in those who are pregnant.[3][14] While not recommended in women who are breastfeeding, those who take a single dose should not generally have to stop breastfeeding.[15] Tramadol is converted in the liver to O-desmethyltramadol (desmetramadol), an opioid with a stronger affinity for the μ-opioid receptor.[3][16]
Tramadol was patented in 1972 and launched under the name "Tramal" in 1977 by the West German pharmaceutical company Grünenthal GmbH.[13][17] In the mid-1990s, it was approved in the United Kingdom and the United States.[13] It is available as a generic medication and marketed under many brand names worldwide.[1][3] In 2021, it was the 41st most commonly prescribed medication in the United States, with more than 15 million prescriptions.[18][19]
- ^ a b c "Tramadol". Drugs.com. Archived from the original on 23 July 2018. Retrieved 22 December 2018.
- ^ "Tramadol Use During Pregnancy". Drugs.com. 14 October 2019. Archived from the original on 13 April 2020. Retrieved 7 February 2020.
- ^ a b c d e f g h i j k "Tramadol Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 12 November 2020. Retrieved 10 April 2024.
- ^ Cite error: The named reference
MedlinePluswas invoked but never defined (see the help page). - ^ 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.
- ^ "Ralivia Product information". Health Canada. 25 April 2012. Archived from the original on 8 May 2021. Retrieved 3 July 2022.
- ^ "Ultram- tramadol hydrochloride tablet, coated". DailyMed. 7 June 2022. Archived from the original on 1 December 2021. Retrieved 3 July 2022.
- ^ "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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "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.
- ^ 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.
- ^ a b British national formulary: BNF 74 (74 ed.). British Medical Association. 2017. pp. 447–448. ISBN 978-0857112989.
- ^ "Tramadol Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 13 April 2020. Retrieved 5 September 2016.
- ^ 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.
- ^ 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.
- ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
- ^ "Tramadol – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.