Substance
ID:78
Names and Identifiers
Brand Name
UltramZydolUltram ERTriduralRalivia FlashtabCrispinRalivia ERTramadol HCl BP/EPTramal
IUPAC name
(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
Synonyms
Tramodol HcltramadolTramadolTramadol HClTramadol hydrochlorideTramadolum [INN-Latin]
IUPAC Traditional name
tramadol
Properties
Physical Property
Hydrophobicity(logP)
2.4
Solubility
Soluble in water.
Molecule Details
Drug Groups
approved; investigational
Description
A narcotic analgesic proposed for moderate to severe pain. It may be habituating. [PubChem]
Indication
Indicated in the treatment of moderate to severe pain. Consider for those prone to constipation or respiratory depression. Tramadol is used to treat postoperative, dental, cancer, and acute musculosketetal pain and as an adjuvant to NSAID therapy in patients with osteoarthritis.
Pharmacology
Tramadol, a centrally-acting analgesic, exists as a racemic mixture of the trans isomer, with important differences in binding, activity, and metabolism associated with the two enantiomers. Although Tramadol is a synthetic analog of codeine, it has a significantly lower affinity for opioid receptors than codeine.
Toxicity
LD50=350mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation
The major metabolic pathways appear to be N- and O- demethylation and glucuronidation or sulfation in the liver. One metabolite (O-desmethyltramadol, denoted M1) is pharmacologically active in animal models.
Absorption
Racemic tramadol is rapidly and almost completely absorbed after oral administration. The mean absolute bioavailability of a 100 mg oral dose is approximately 75%.The mean peak plasma concentration of racemic tramadol and M1 occurs at two and three hours, respectively, after administration in healthy adults.
Half Life
23 +/- 10 minutes
Protein Binding
20%
Elimination
Tramadol is eliminated primarily through metabolism by the liver and the metabolites are eliminated primarily by the kidneys. Tramadol and its metabolites are excreted primarily in the urine with observed plasma half-lives of 6.3 and 7.4 hours for tramadol and M1, respectively. Approximately 30% of the dose is excreted in the urine as unchanged drug, whereas 60% of the dose is excreted as metabolites.
Distribution
* 2.6 L/kg [male 100 mg intravenous dose]
* 2.9 L/kg [female 100 mg intravenous dose]
* 2.9 L/kg [female 100 mg intravenous dose]
Clearance
* 5.9 mL/min/Kg [Healthy Adults, 100 mg qid, MD p.o]
* 8.5 mL/min/Kg [Healthy Adults, 100 mg SD p.o]
* 6.89 mL/min/Kg [Geriatric, (<75 yr), 50 mg SD p.o.]
* 4.23 mL/min/Kg [Hepatic Impaired, 50 mg SD p.o.]
* 4.23 mL/min/Kg [Renal Impaired, Clcr10-3mL/min, 100 mg SD i.v.]
* 3.73 mL/min/Kg [Renal Impaired, CLcr<5 mL/min, 100 mg SD i.v.]
* 6.4 mL/min/Kg [Male following a 100 mg IV dose]
* 5.7 mL/min/Kg [Female following a 100 mg IV dose]
* 8.5 mL/min/Kg [Healthy Adults, 100 mg SD p.o]
* 6.89 mL/min/Kg [Geriatric, (<75 yr), 50 mg SD p.o.]
* 4.23 mL/min/Kg [Hepatic Impaired, 50 mg SD p.o.]
* 4.23 mL/min/Kg [Renal Impaired, Clcr10-3mL/min, 100 mg SD i.v.]
* 3.73 mL/min/Kg [Renal Impaired, CLcr<5 mL/min, 100 mg SD i.v.]
* 6.4 mL/min/Kg [Male following a 100 mg IV dose]
* 5.7 mL/min/Kg [Female following a 100 mg IV dose]
References
•
Dayer P, Desmeules J, Collart L: [Pharmacology of tramadol] Drugs. 1997;53 Suppl 2:18-24.
[Pubmed]
•
Harati Y, Gooch C, Swenson M, Edelman S, Greene D, Raskin P, Donofrio P, Cornblath D, Sachdeo R, Siu CO, Kamin M: Double-blind randomized trial of tramadol for the treatment of the pain of diabetic neuropathy. Neurology. 1998 Jun;50(6):1842-6.
[Pubmed]
•
Harati Y, Gooch C, Swenson M, Edelman SV, Greene D, Raskin P, Donofrio P, Cornblath D, Olson WH, Kamin M: Maintenance of the long-term effectiveness of tramadol in treatment of the pain of diabetic neuropathy. J Diabetes Complications. 2000 Mar-Apr;14(2):65-70.
[Pubmed]
•
Gobel H, Stadler T: [Treatment of post-herpes zoster pain with tramadol. Results of an open pilot study versus clomipramine with or without levomepromazine] Drugs. 1997;53 Suppl 2:34-9.
[Pubmed]
•
Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• Harati Y, Gooch C, Swenson M, Edelman SV, Greene D, Raskin P, Donofrio P, Cornblath D, Olson WH, Kamin M: Maintenance of the long-term effectiveness of tramadol in treatment of the pain of diabetic neuropathy. J Diabetes Complications. 2000 Mar-Apr;14(2):65-70. Pubmed
• Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31. Pubmed
• Gobel H, Stadler T: [Treatment of post-herpes zoster pain with tramadol. Results of an open pilot study versus clomipramine with or without levomepromazine] Drugs. 1997;53 Suppl 2:34-9. Pubmed
• Dayer P, Desmeules J, Collart L: [Pharmacology of tramadol] Drugs. 1997;53 Suppl 2:18-24. Pubmed
• Harati Y, Gooch C, Swenson M, Edelman S, Greene D, Raskin P, Donofrio P, Cornblath D, Sachdeo R, Siu CO, Kamin M: Double-blind randomized trial of tramadol for the treatment of the pain of diabetic neuropathy. Neurology. 1998 Jun;50(6):1842-6. Pubmed