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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
Structure of KETOBEMIDONE

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

HIDE SMILES / InChI

Description

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
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
Identification of phase I and phase II metabolites of ketobemidone in patient urine using liquid chromatography-electrospray tandem mass spectrometry.
2001 Nov 5
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 are not affected by CYP2D6 or CYP2C19 phenotype.
2002 Feb
Effects of clonidine on postoperative nausea and vomiting in breast cancer surgery.
2002 May
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
Postoperative pain after abdominal hysterectomy: a double-blind comparison between placebo and local anesthetic infused intraperitoneally.
2004 Oct
Postoperative continuous intrathecal pain treatment in children after selective dorsal rhizotomy with bupivacaine and two different morphine doses.
2006 Apr
Performance of four mixed-mode solid-phase extraction columns applied to basic drugs in urine.
2007
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
Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children.
2010 Apr
Patents

Patents

JP2002517462A
7

Sample Use Guides

In Vivo Use Guide
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).
Name Type Language
KETOBEMIDONE
INN   MI   WHO-DD  
INN  
Official Name English
IDS-NK-001(SECT.3)
Code English
1-(4-(M-HYDROXYPHENYL)-1-METHYL-4-PIPERIDYL)-1-PROPANONE
Systematic Name English
CETOBEMIDONE
Common Name English
KETOBEMIDONE [MI]
Common Name English
Ketobemidone [WHO-DD]
Common Name English
A 21 LUNDBECK
Common Name English
4-(M-HYDROXYPHENYL)-1-METHYL-4-PROPIONYLPIPERIDINE
Systematic Name English
IDS-NK-001
Code English
NSC-117863
Code English
ketobemidone [INN]
Common Name English
CLIRADONE
Common Name English
CIBA 7115
Common Name English
Classification Tree Code System Code
WHO-VATC QN02AG02
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WHO-VATC QN02AB01
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WHO-ATC N02AG02
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WHO-ATC N02AB01
Created by admin on Fri Dec 15 16:04:50 GMT 2023 , Edited by admin on Fri Dec 15 16:04:50 GMT 2023
DEA NO. 9628
Created by admin on Fri Dec 15 16:04:50 GMT 2023 , Edited by admin on Fri Dec 15 16:04:50 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
Code System Code Type Description
NSC
117863
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PRIMARY
INN
1274
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PRIMARY
MESH
C012394
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PRIMARY
FDA UNII
PQS1L514CF
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PRIMARY
EVMPD
SUB08370MIG
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PRIMARY
EPA CompTox
DTXSID00196977
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PRIMARY
DRUG BANK
DB06738
Created by admin on Fri Dec 15 16:04:50 GMT 2023 , Edited by admin on Fri Dec 15 16:04:50 GMT 2023
PRIMARY
WIKIPEDIA
KETOBEMIDONE
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
DRUG CENTRAL
1526
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PRIMARY
SMS_ID
100000083095
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PRIMARY
CAS
469-79-4
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PRIMARY
NCI_THESAURUS
C80583
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PRIMARY
MERCK INDEX
m6618
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PRIMARY Merck Index
PUBCHEM
10101
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-421-0
Created by admin on Fri Dec 15 16:04:50 GMT 2023 , Edited by admin on Fri Dec 15 16:04:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL47072
Created by admin on Fri Dec 15 16:04:50 GMT 2023 , Edited by admin on Fri Dec 15 16:04:50 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of KETOBEMIDONE
SALT/SOLVATE (PARENT)
Structure of KETOBEMIDONE HYDROCHLORIDE
NIH
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