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Clinical data | |||
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Trade names | Ultram, Zytram, others | ||
AHFS/Drugs.com | Monograph | ||
MedlinePlus | a695011 | ||
License data | |||
Pregnancy category |
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Dependence liability |
Present | ||
Routes of administration |
By mouth, IV, IM, rectal | ||
ATC code | N02AX02 (WHO) | ||
Legal status | |||
Legal status |
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Pharmacokinetic data | |||
Bioavailability | 70–75% (oral), 77% (rectal), 100% (IM) | ||
Protein binding | 20% | ||
Metabolism | Liver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4 | ||
Biological half-life | 6.3 ± 1.4 hr | ||
Excretion | Urine (95%) | ||
Identifiers | |||
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CAS Number | 27203-92-5 | ||
PubChem (CID) | 33741 | ||
DrugBank | DB00193 | ||
ChemSpider | 31105 | ||
UNII | 39J1LGJ30J | ||
KEGG | D08623 | ||
ChEBI | CHEBI:9648 | ||
ChEMBL | CHEMBL1066 | ||
ECHA InfoCard | 100.043.912 | ||
Chemical and physical data | |||
Formula | C16H25NO2 | ||
Molar mass | 263.4 g/mol | ||
3D model (Jmol) | Interactive image | ||
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(what is this?) |
Tramadol, sold under the brandname Ultram among others, is an opioid pain medication used to treat moderate to moderately severe pain. When taken as an immediate-release oral formulation, the onset of pain relief usually occurs within about an hour. It has two different mechanisms. First, it binds to the μ-opioid receptor. Second, it inhibits the reuptake of serotonin and norepinephrine.
Serious side effects may include seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction, although the risk of serotonin syndrome appears to be low. Common side effects include: constipation, itchiness and nausea, among others. 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. While not recommended in women who are breastfeeding, those who take it should not stop breastfeeding.
Tramadol is marketed as a racemic mixture of both R- and S-stereoisomers. This is because the two isomers complement each other's analgesic activity. It is often combined with paracetamol (acetaminophen) as this is known to improve the efficacy of tramadol in relieving pain. Tramadol is metabolized to O-desmethyltramadol, which is a more potent opioid. It is of the benzenoid class.
Tramadol was launched and marketed as "Tramal" by the German pharmaceutical company Grünenthal GmbH in 1977 in West Germany, and 20 years later it was launched in countries such as the UK, US, and Australia. It is marketed under many brand names worldwide.