KETOBEMIDONE HYDROCHLORIDE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB06738 | https://www.ncbi.nlm.nih.gov/pubmed/9553996 | https://www.ncbi.nlm.nih.gov/pubmed/9783723 | https://www.ncbi.nlm.nih.gov/pubmed/12492604

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	6794076
Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration.	1981 Feb	7215421
Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man.	1981 Jul-Aug	6114838
Disappearance of morphine-induced hyperalgesia after discontinuing or substituting morphine with other opioid agonists.	1994 Nov	7892029
Improved recovery after music and therapeutic suggestions during general anaesthesia: a double-blind randomised controlled trial.	2001 Aug	11472279
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	11948848
The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype.	2002 Feb	11936707
Effects of clonidine on postoperative nausea and vomiting in breast cancer surgery.	2002 May	11981150
Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry.	2003 Jun 15	12742125
Similar pain scores after early and late extubation in heart surgery with cardiopulmonary bypass.	2004 Feb	14973802
Laparoscopic occlusion of uterine vessels for the treatment of symptomatic fibroids: Initial experience and comparison to uterine artery embolization.	2004 Jan	14749632
Stability of drugs in stored postmortem femoral blood and vitreous humor.	2004 Jul	15317202
Postoperative pain after abdominal hysterectomy: a double-blind comparison between placebo and local anesthetic infused intraperitoneally.	2004 Oct	15385371
Intravenous acetaminophen reduced the use of opioids compared with oral administration after coronary artery bypass grafting.	2005 Jun	16130055
Fracture risk associated with the use of morphine and opiates.	2006 Jul	16789982
[The use of analgesics in Denmark, 2000-2004].	2006 May 15	16768899
Laparoscopic occlusion compared with embolization of uterine vessels: a randomized controlled trial.	2007 Jan	17197583
Preoperative sub-Tenon's capsule injection of ropivacaine in conjunction with general anesthesia in retinal detachment surgery.	2007 Nov	17445898
Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs.	2008 Jun 15	18499452
Simultaneous analysis of five antidepressant drugs using direct injection of biofluids in a capillary restricted-access media-liquid chromatography-tandem mass spectrometry system.	2008 May 2	18355831
In vivo investigation of brain and systemic ketobemidone metabolism.	2010 Feb	20098777

Patents

Sample Use Guides

In Vivo Use Guide

Oral Light 5mg Common 5-10mg Strong 10-15mg.

Route of Administration: Oral

In Vitro Use Guide

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 HYDROCHLORIDE

Common Name

English

KETOBEMIDONE HYDROCHLORIDE [MART.]

Common Name

English

1-(4-(3-HYDROXYPHENYL)-1-METHYL-4-PIPERIDINYL)-1-PROPANONE HYDROCHLORIDE

Systematic Name

English

HOECHST 10720

Code

English

KETODUR

Common Name

English

WIN-1539

Code

English

Ketobemidone hydrochloride [WHO-DD]

Common Name

English

KETOBEMIDONE HYDROCHLORIDE [MI]

Common Name

English

KETOBEMIDONE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

KETOBEMIDONE HCL

Common Name

English

CYMIDON

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413