Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H21NO2 |
| Molecular Weight | 247.3327 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)C1(CCN(C)CC1)C2=CC=CC(O)=C2
InChI
InChIKey=ALFGKMXHOUSVAD-UHFFFAOYSA-N
InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
| Molecular Formula | C15H21NO2 |
| Molecular Weight | 247.3327 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon) is a strong opioid analgesic, structurally related to pethidine, which has been in clinical use for more
than 50 years. In the Scandinavian countries ketobemidone is only available in combination with a spasmolytic
substance N,N-dimethyl-3,3-diphenyl-I-methylallylamine
(A29). Ketobemidone has been shown to be a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist. In spite of a relatively low mu-receptor affinity ketobemidone has a higher analgesic potency than morphine by
systemic administration. It is probably due to its higher
lipophilicity and consequently more easy penetration into
the CNS. Ketobemidone is indicated for the treatment of all types of severe pain, such as postoperative, cancer, kidney stones and fractures.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
|
| Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration. | 1981 Feb |
|
| Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man. | 1981 Jul-Aug |
|
| Disappearance of morphine-induced hyperalgesia after discontinuing or substituting morphine with other opioid agonists. | 1994 Nov |
|
| Improved recovery after music and therapeutic suggestions during general anaesthesia: a double-blind randomised controlled trial. | 2001 Aug |
|
| Identification of phase I and phase II metabolites of ketobemidone in patient urine using liquid chromatography-electrospray tandem mass spectrometry. | 2001 Nov 5 |
|
| Perioperative hypothermia and postoperative opioid requirements. | 2001 Oct |
|
| Identification of glucuronide conjugates of ketobemidone and its phase I metabolites in human urine utilizing accurate mass and tandem time-of-flight mass spectrometry. | 2002 Apr |
|
| Postoperative pain relief using intermittent injections of 0.5% ropivacaine through a catheter after laparoscopic cholecystectomy. | 2002 Aug |
|
| The pharmacokinetics of ketobemidone in critically ill patients. | 2002 Dec |
|
| The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype. | 2002 Feb |
|
| Effects of clonidine on postoperative nausea and vomiting in breast cancer surgery. | 2002 May |
|
| N-(trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones. | 2003 Jan 2 |
|
| Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. | 2003 Jun 15 |
|
| Laparoscopic occlusion of uterine vessels for the treatment of symptomatic fibroids: Initial experience and comparison to uterine artery embolization. | 2004 Jan |
|
| Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. | 2005 Aug |
|
| Intravenous acetaminophen reduced the use of opioids compared with oral administration after coronary artery bypass grafting. | 2005 Jun |
|
| Postoperative continuous intrathecal pain treatment in children after selective dorsal rhizotomy with bupivacaine and two different morphine doses. | 2006 Apr |
|
| Fracture risk associated with the use of morphine and opiates. | 2006 Jul |
|
| [The use of analgesics in Denmark, 2000-2004]. | 2006 May 15 |
|
| In vivo investigation of brain and systemic ketobemidone metabolism. | 2010 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://drugs.tripsit.me/ketobemidone
Curator's Comment: The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection. https://www.drugbank.ca/drugs/DB06738
Oral
Light 5mg
Common 5-10mg
Strong 10-15mg.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Affinities of ketobemidone and morphine for Mu, Delta and Kappa opioid
receptors in bovine caudate nucleus were determined.
The affinity of ketobemidone to the mu-receptor is significantly lower than that of morphine considering Ki values of
5.5 and 2.4 nM respectively. At the delta-binding site the
two opioids have equal affinity (Ki values 143 versus 136
nM), whereas ketobemidone has much lower affinity than
morphine to the kappa-receptor (Ki 599 versus 130 nM).
| Substance Class |
Chemical
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PQS1L514CF
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Validated (UNII)
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WHO-VATC |
QN02AG02
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WHO-VATC |
QN02AB01
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N02AG02
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N02AB01
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DEA NO. |
9628
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NCI_THESAURUS |
C67413
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117863
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1274
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C012394
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PQS1L514CF
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SUB08370MIG
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DTXSID00196977
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DB06738
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KETOBEMIDONE
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1526
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100000083095
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469-79-4
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C80583
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m6618
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10101
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207-421-0
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CHEMBL47072
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APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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ACTIVE MOIETY |
