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
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Wound infiltration with ropivacaine and fentanyl: effects on postoperative pain and PONV after breast surgery. | 2003 Mar |
|
| Stability of drugs in stored postmortem femoral blood and vitreous humor. | 2004 Jul |
|
| Fatal intoxications in a Swedish forensic autopsy material during 1992-2002. | 2004 Jun 30 |
|
| Comparison of the analgesic efficacy of ketobemidone and morphine for management of postoperative pain in children: a randomized, controlled study. | 2004 Nov |
|
| Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. | 2005 Aug |
|
| The effect of gabapentin on post-operative pain following tonsillectomy in adults. | 2006 Aug |
|
| Performance of four mixed-mode solid-phase extraction columns applied to basic drugs in urine. | 2007 |
|
| Gabapentin and postoperative pain: a qualitative and quantitative systematic review, with focus on procedure. | 2007 Jul 7 |
|
| Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs. | 2008 Jun 15 |
|
| Method development for identification of ketobemidone metabolites in microdialysate samples by coupled-column capillary liquid chromatography-tandem mass spectrometry. | 2008 May 2 |
|
| Intraabdominal local anaesthetics for postoperative pain relief following abdominal hysterectomy: a randomized, double-blind, dose-finding study. | 2009 May |
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).
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WHO-VATC |
QN02AG02
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WHO-VATC |
QN02AB01
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WHO-ATC |
N02AG02
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WHO-ATC |
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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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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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
