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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
The pharmacokinetics of ketobemidone in critically ill patients. | 2002 Dec |
|
Laparoscopic occlusion of uterine vessels for the treatment of symptomatic fibroids: Initial experience and comparison to uterine artery embolization. | 2004 Jan |
|
Stability of drugs in stored postmortem femoral blood and vitreous humor. | 2004 Jul |
|
Fatal intoxications in a Swedish forensic autopsy material during 1992-2002. | 2004 Jun 30 |
|
Intravenous acetaminophen reduced the use of opioids compared with oral administration after coronary artery bypass grafting. | 2005 Jun |
|
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 |
|
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 |
|
In vivo investigation of brain and systemic ketobemidone metabolism. | 2010 Feb |
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:04:50 UTC 2023
by
admin
on
Fri Dec 15 16:04:50 UTC 2023
|
Record UNII |
PQS1L514CF
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |