User:Mr. Ibrahem/Tramadol
From Wikipedia, the free encyclopedia
Tramadol, sold under the brand name Ultram among others,[1] is an opioid pain medication used to treat moderate to moderately severe pain.[3] It is generally less preferred than other pain medication.[9] 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.[10] It may be sold in combination with paracetamol (acetaminophen) or as longer-acting formulations.[3][10]
Clinical data | |
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Pronunciation | tra' ma dole |
Trade names | Ultram, Zytram, others[1] |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695011 |
License data | |
Pregnancy category |
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Dependence liability | Present[3] |
Routes of administration | By mouth, IV, IM, rectal |
Drug class | Opiate analgesic[4] |
Legal status | |
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Pharmacokinetic data | |
Bioavailability | 70–75% (by mouth), 77% (rectal), 100% (IM)[5] |
Protein binding | 20%[3] |
Metabolism | Liver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4[5][6] |
Metabolites | O-desmethyltramadol, N-desmethyltramadol |
Onset of action | Less than 1 hour (by mouth)[3] |
Elimination half-life | 6.3 ± 1.4 h[6] |
Duration of action | 6 hours[7] |
Excretion | Urine (95%)[8] |
Identifiers | |
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Chemical and physical data | |
Formula | C16H25NO2 |
Molar mass | 263.381 g·mol−1 |
3D model (JSmol) | |
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 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][10] While not recommended in women who are breastfeeding, those who take a single dose should not generally stop breastfeeding.[11] Tramadol is converted in the liver to O-desmethyltramadol (desmetramadol), an opioid with stronger binding to the μ-opioid receptor.[3][12] Tramadol is also a serotonin–norepinephrine reuptake inhibitor (SNRI).[3][13]
Tramadol was patented in 1963 and launched under the name "Tramal" in 1977 by the West German pharmaceutical company Grünenthal GmbH.[13][14] 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.[3][1] In the United States, the wholesale cost is less than US$0.05 per dose as of 2018.[15] In Canada it costs about 1.20 CAD per dose as of 2021.[9] In 2017, it was the 32nd most commonly prescribed medication in the United States, with more than 21 million prescriptions.[16][17]