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Tramadol

Tramadol
Tramadol as a racemic mixture.svg
R-tramadol3Dan2.gif S-tramadol3Dan2.gif
Clinical data
Trade names Ultram, Zytram, others
AHFS/Drugs.com Monograph
MedlinePlus a695011
License data
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Dependence
liability
Present
Routes of
administration
By mouth, IV, IM, rectal
ATC code N02AX02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: Class C – Schedule 3 CD
  • US: Schedule IV
  • ℞ (Prescription only)
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
CAS Number 27203-92-5 YesY
PubChem (CID) 33741
DrugBank DB00193 YesY
ChemSpider 31105 YesY
UNII 39J1LGJ30J YesY
KEGG D08623 YesY
ChEBI CHEBI:9648 N
ChEMBL CHEMBL1066 YesY
ECHA InfoCard 100.043.912
Chemical and physical data
Formula C16H25NO2
Molar mass 263.4 g/mol
3D model (Jmol) Interactive image
 NYesY (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.


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