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 |
|---|---|---|
| Determination of 19 drugs of abuse and metabolites in whole blood by high-performance liquid chromatography-tandem mass spectrometry. | 2010-04 |
|
| Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children. | 2010-04 |
|
| In vivo investigation of brain and systemic ketobemidone metabolism. | 2010-02 |
|
| Intraabdominal local anaesthetics for postoperative pain relief following abdominal hysterectomy: a randomized, double-blind, dose-finding study. | 2009-05 |
|
| Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs. | 2008-06-15 |
|
| Simultaneous analysis of five antidepressant drugs using direct injection of biofluids in a capillary restricted-access media-liquid chromatography-tandem mass spectrometry system. | 2008-05-02 |
|
| Method development for identification of ketobemidone metabolites in microdialysate samples by coupled-column capillary liquid chromatography-tandem mass spectrometry. | 2008-05-02 |
|
| Preoperative sub-Tenon's capsule injection of ropivacaine in conjunction with general anesthesia in retinal detachment surgery. | 2007-11 |
|
| Gabapentin and postoperative pain: a qualitative and quantitative systematic review, with focus on procedure. | 2007-07-07 |
|
| Laparoscopic occlusion compared with embolization of uterine vessels: a randomized controlled trial. | 2007-01 |
|
| Performance of four mixed-mode solid-phase extraction columns applied to basic drugs in urine. | 2007 |
|
| The effect of gabapentin on post-operative pain following tonsillectomy in adults. | 2006-08 |
|
| Fracture risk associated with the use of morphine and opiates. | 2006-07 |
|
| [The use of analgesics in Denmark, 2000-2004]. | 2006-05-15 |
|
| Postoperative continuous intrathecal pain treatment in children after selective dorsal rhizotomy with bupivacaine and two different morphine doses. | 2006-04 |
|
| Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. | 2005-08 |
|
| Intravenous acetaminophen reduced the use of opioids compared with oral administration after coronary artery bypass grafting. | 2005-06 |
|
| Comparison of the analgesic efficacy of ketobemidone and morphine for management of postoperative pain in children: a randomized, controlled study. | 2004-11 |
|
| Postoperative pain after abdominal hysterectomy: a double-blind comparison between placebo and local anesthetic infused intraperitoneally. | 2004-10 |
|
| Stability of drugs in stored postmortem femoral blood and vitreous humor. | 2004-07 |
|
| Fatal intoxications in a Swedish forensic autopsy material during 1992-2002. | 2004-06-30 |
|
| Ibuprofen vs. acetaminophen vs. ibuprofen and acetaminophen after arthroscopically assisted anterior cruciate ligament reconstruction. | 2004-06 |
|
| Similar pain scores after early and late extubation in heart surgery with cardiopulmonary bypass. | 2004-02 |
|
| Laparoscopic occlusion of uterine vessels for the treatment of symptomatic fibroids: Initial experience and comparison to uterine artery embolization. | 2004-01 |
|
| Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. | 2003-06-15 |
|
| Wound infiltration with ropivacaine and fentanyl: effects on postoperative pain and PONV after breast surgery. | 2003-03 |
|
| N-(trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones. | 2003-01-02 |
|
| The pharmacokinetics of ketobemidone in critically ill patients. | 2002-12 |
|
| Postoperative pain relief using intermittent injections of 0.5% ropivacaine through a catheter after laparoscopic cholecystectomy. | 2002-08 |
|
| Effects of clonidine on postoperative nausea and vomiting in breast cancer surgery. | 2002-05 |
|
| Identification of glucuronide conjugates of ketobemidone and its phase I metabolites in human urine utilizing accurate mass and tandem time-of-flight mass spectrometry. | 2002-04 |
|
| The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype. | 2002-02 |
|
| Identification of phase I and phase II metabolites of ketobemidone in patient urine using liquid chromatography-electrospray tandem mass spectrometry. | 2001-11-05 |
|
| Perioperative hypothermia and postoperative opioid requirements. | 2001-10 |
|
| Determination of ketobemidone and its metabolites in plasma and urine using solid-phase extraction and liquid chromatography-mass spectrometry. | 2001-08 |
|
| Improved recovery after music and therapeutic suggestions during general anaesthesia: a double-blind randomised controlled trial. | 2001-08 |
|
| Disappearance of morphine-induced hyperalgesia after discontinuing or substituting morphine with other opioid agonists. | 1994-11 |
|
| Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man. | 1981-07-01 |
|
| Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration. | 1981-02 |
|
| Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
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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QN02AG02
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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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1274
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C012394
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DB06738
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KETOBEMIDONE
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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 |
