Tramadol
Medication of the opioid type, patented 1972 / From Wikipedia, the free encyclopedia
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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).
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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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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 | ||
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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.[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]