Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H21NO2.ClH |
Molecular Weight | 283.794 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCC(=O)C1(CCN(C)CC1)C2=CC=CC(O)=C2
InChI
InChIKey=HYDFAZFVKRXNJX-UHFFFAOYSA-N
InChI=1S/C15H21NO2.ClH/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;1H
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
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Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration. | 1981 Feb |
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Disappearance of morphine-induced hyperalgesia after discontinuing or substituting morphine with other opioid agonists. | 1994 Nov |
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Improved recovery after music and therapeutic suggestions during general anaesthesia: a double-blind randomised controlled trial. | 2001 Aug |
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N-(trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones. | 2003 Jan 2 |
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Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. | 2003 Jun 15 |
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Wound infiltration with ropivacaine and fentanyl: effects on postoperative pain and PONV after breast surgery. | 2003 Mar |
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Laparoscopic occlusion of uterine vessels for the treatment of symptomatic fibroids: Initial experience and comparison to uterine artery embolization. | 2004 Jan |
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Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. | 2005 Aug |
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Postoperative continuous intrathecal pain treatment in children after selective dorsal rhizotomy with bupivacaine and two different morphine doses. | 2006 Apr |
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The effect of gabapentin on post-operative pain following tonsillectomy in adults. | 2006 Aug |
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Fracture risk associated with the use of morphine and opiates. | 2006 Jul |
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[The use of analgesics in Denmark, 2000-2004]. | 2006 May 15 |
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Performance of four mixed-mode solid-phase extraction columns applied to basic drugs in urine. | 2007 |
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Laparoscopic occlusion compared with embolization of uterine vessels: a randomized controlled trial. | 2007 Jan |
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Gabapentin and postoperative pain: a qualitative and quantitative systematic review, with focus on procedure. | 2007 Jul 7 |
|
Preoperative sub-Tenon's capsule injection of ropivacaine in conjunction with general anesthesia in retinal detachment surgery. | 2007 Nov |
|
Intraabdominal local anaesthetics for postoperative pain relief following abdominal hysterectomy: a randomized, double-blind, dose-finding study. | 2009 May |
|
Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children. | 2010 Apr |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8153059
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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C67413
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ACTIVE MOIETY
SUBSTANCE RECORD