Tramadol
Tramadol, sold under the brand name Ultram among others, is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderately 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).
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| Pronunciation | tra' ma doll |
| Trade names | Ultram, Zytram, Ralivia, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a695011 |
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| Dependence liability | Low–moderate |
| Routes of administration | By mouth, intravenous (IV), intramuscular (IM), rectal |
| Drug class | Opioid analgesic |
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| Pharmacokinetic data | |
| Bioavailability | 70–75% (by mouth), 77% (rectal), 100% (IM) |
| Protein binding | 20% |
| Metabolism | Liver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4 |
| Metabolites | O-desmethyltramadol N-desmethyltramadol |
| Onset of action | Less than 1 hour (by mouth) |
| Elimination half-life | 6.3 ± 1.4 h |
| Duration of action | 6 hours |
| Excretion | Urine (95%) |
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| ECHA InfoCard | 100.043.912 |
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| 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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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 name "Tramal" in 1977 by the West German pharmaceutical company Grünenthal 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 2021, it was the 41st most commonly prescribed medication in the United States, with more than 15 million prescriptions.