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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
Determination of ketobemidone and its metabolites in plasma and urine using solid-phase extraction and liquid chromatography-mass spectrometry.
2001 Aug
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
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
Ibuprofen vs. acetaminophen vs. ibuprofen and acetaminophen after arthroscopically assisted anterior cruciate ligament reconstruction.
2004 Jun
Comparison of the analgesic efficacy of ketobemidone and morphine for management of postoperative pain in children: a randomized, controlled study.
2004 Nov
Fracture risk associated with the use of morphine and opiates.
2006 Jul
[The use of analgesics in Denmark, 2000-2004].
2006 May 15
Laparoscopic occlusion compared with embolization of uterine vessels: a randomized controlled trial.
2007 Jan
Determination of 19 drugs of abuse and metabolites in whole blood by high-performance liquid chromatography-tandem mass spectrometry.
2010 Apr
In vivo investigation of brain and systemic ketobemidone metabolism.
2010 Feb
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
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
WHO-VATC QN02AB01
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
WHO-ATC N02AG02
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
WHO-ATC N02AB01
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
DEA NO. 9628
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
Code System Code Type Description
NSC
117863
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
PRIMARY
INN
1274
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
MESH
C012394
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
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FDA UNII
PQS1L514CF
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
EVMPD
SUB08370MIG
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID00196977
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
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DRUG BANK
DB06738
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
WIKIPEDIA
KETOBEMIDONE
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
PRIMARY
DRUG CENTRAL
1526
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
SMS_ID
100000083095
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
PRIMARY
CAS
469-79-4
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
NCI_THESAURUS
C80583
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
PRIMARY
MERCK INDEX
m6618
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY Merck Index
PUBCHEM
10101
Created by admin on Fri Dec 15 16:04:51 UTC 2023 , Edited by admin on Fri Dec 15 16:04:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-421-0
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL47072
Created by admin on Fri Dec 15 16:04:50 UTC 2023 , Edited by admin on Fri Dec 15 16:04:50 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of KETOBEMIDONE
SALT/SOLVATE (PARENT)
Structure of KETOBEMIDONE HYDROCHLORIDE
NIH
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