Page last updated: 2024-12-05

ketobemidone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

ketobemidone: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10101
CHEMBL ID47072
CHEBI ID6125
SCHEMBL ID24574
MeSH IDM0059391

Synonyms (69)

Synonym
einecs 207-421-0
cetobemidonum [inn-latin]
cymidon (van)
4-(m-hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketone
nsc 117863
dea no. 9628
cetobemidone [inn-french]
1-propanone, 1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-
ketobemidonum
cetobemidona [inn-spanish]
1-propanone, 1-(4-(3-hydroxyphenyl)-1-methyl-4-piperidinyl)-
ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketone
1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanone
4-(m-hydroxyphenyl)-1-methyl-4-propionylpiperidine
1-(4-(3-hydroxyphenyl)-1-methyl-4-piperidinyl)-1-propanone
brn 0218226
chetobemidone [dcit]
ketogan
469-79-4
k 4710
1-propanone, 1-[4-(3-hydroxyphenyl)-1-methyl-4-piperidinyl]-
cetobemidon
wln: t6ntj a1 bv2 dr cq
cymidon
cliradon
nsc-117863
cetobemidone
ketobemidone
ciba 7115
ethyl [4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl ketone
hoechst 10720
win 1539
1-propanone, 1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-
keytobemidone hydrochloride
nsc117863
cliradone
1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone
a 21 lundbeck
ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidyl
chebi:6125 ,
CHEMBL47072
ketodur
ids-nk-001(sect.3)
ids-nk-001
ketorax
1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
ketobemidone (inn)
D08100
cetobemidonum
pqs1l514cf ,
cetobemidona
chetobemidone
ketobemidone [inn:ban]
unii-pqs1l514cf
4-21-00-06106 (beilstein handbook reference)
DB06738
SCHEMBL24574
ketobemidone [inn]
ketobemidone [mi]
ketobemidone [who-dd]
1-[4-(3-hydroxyphenyl)-1-methyl-4-piperidinyl]-1-propanone #
ALFGKMXHOUSVAD-UHFFFAOYSA-N
DTXSID00196977
HY-B2092
CS-6592
{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}
ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketone
Q2471714
bdbm50231237

Research Excerpts

Effects

ExcerptReferenceRelevance
"Ketobemidone has been used as an analgesic for postoperative pain in children, but to our knowledge the effect and occurrence of adverse effects of ketobemidone compared to morphine is not known. "( Comparison of the analgesic efficacy of ketobemidone and morphine for management of postoperative pain in children: a randomized, controlled study.
Jylli, L; Langius-Eklöf, A; Lundeberg, S; Olsson, GL, 2004
)
2.03

Pharmacokinetics

The pharmacokinetic parameters of ketobemidone in children older than 1 month appear to be similar to those in adults. The median (range) values for ketobamidone clearance, apparent volume of distribution, volume of central compartment, distribution half-life and elimination half- life were 0.

ExcerptReferenceRelevance
" The mean plasma half-life of elimination (t1/2 beta) was about the same following oral (2."( Clinical pharmacokinetics and oral bioavailability of ketobemidone.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1980
)
0.51
"The pharmacokinetic constants and rectal bioavailability of the narcotic analgesic ketobemidone were determined in six male patients after surgery."( Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1981
)
0.78
" The pharmacokinetic analysis was performed using WinNonlin trade mark software."( The pharmacokinetics of ketobemidone in critically ill patients.
Al-Shurbaji, A; Tokics, L, 2002
)
0.62
"There was a wide variation in the different pharmacokinetic parameters among patients."( The pharmacokinetics of ketobemidone in critically ill patients.
Al-Shurbaji, A; Tokics, L, 2002
)
0.62
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35
" Pharmacokinetic parameters were determined using compartmental methods."( Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children.
Eksborg, S; Lafolie, P; Lundeberg, S; Olsson, GL; Stephanson, N; Stiller, CO, 2010
)
0.6
"Six children were excluded from pharmacokinetic analysis because of incomplete blood sampling."( Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children.
Eksborg, S; Lafolie, P; Lundeberg, S; Olsson, GL; Stephanson, N; Stiller, CO, 2010
)
0.6
"The pharmacokinetic parameters of ketobemidone in children older than 1 month appear to be similar to those in adults."( Pharmacokinetics after an intravenous single dose of the opioid ketobemidone in children.
Eksborg, S; Lafolie, P; Lundeberg, S; Olsson, GL; Stephanson, N; Stiller, CO, 2010
)
0.88
" In an earlier study, we have examined the pharmacokinetic properties in children in different age groups but have not focused on neonates."( Pharmacokinetics after a single intravenous dose of the opioid ketobemidone in neonates.
Eksborg, S; Lundeberg, S; Stephanson, N; Stiller, CO, 2012
)
0.62
" Pharmacokinetic parameters were calculated with standard compartmental methods."( Pharmacokinetics after a single intravenous dose of the opioid ketobemidone in neonates.
Eksborg, S; Lundeberg, S; Stephanson, N; Stiller, CO, 2012
)
0.62
" Despite a low pharmacokinetic variability of ketobemidone as observed in the present neonatal patient population, we recommend individualizing the dose of ketobemidone based on observations of analgesic efficacy."( Pharmacokinetics after a single intravenous dose of the opioid ketobemidone in neonates.
Eksborg, S; Lundeberg, S; Stephanson, N; Stiller, CO, 2012
)
0.88

Compound-Compound Interactions

ExcerptReferenceRelevance
"Continuous Reaction Time (CRT) was measured in cancer patients receiving peripherally acting analgesics either alone (n = 16) or in combination with opioids (n = 16)."( Reaction time in cancer patients receiving peripherally acting analgesics alone or in combination with opioids.
Banning, A; Kaiser, F; Sjøgren, P, 1992
)
0.28

Bioavailability

The single-dose kinetics and the oral and rectal bioavailability of ketobemidone have been studied in patients after surgery.

ExcerptReferenceRelevance
"90 (SD) and the mean relative bioavailability of the mixture was slightly above 100%."( Analgesic effect and bioavailability of oral ketogan given as tablets or mixture to patients with chronic pain of malignant origin.
Kjaer, M; Nielsen, H, 1988
)
0.27
"The basic pharmacokinetics and oral bioavailability of ketobenmidone have been studied in 6 patients after surgery."( Clinical pharmacokinetics and oral bioavailability of ketobemidone.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1980
)
0.51
"The single-dose kinetics and the oral and rectal bioavailability of ketobemidone have been studied in patients after surgery."( Single-dose kinetics and bioavailability of ketobemidone.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1982
)
0.76
"The pharmacokinetic constants and rectal bioavailability of the narcotic analgesic ketobemidone were determined in six male patients after surgery."( Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1981
)
0.78

Dosage Studied

The low oral bioavailability and rapid elimination of ketobemidone demonstrated in this study suggest that the usual dosage recommendation for oral Ketogin in patients with severe pain is too low. Individual dosing based on the clinical response and therapeutic drug monitoring is recommended.

ExcerptRelevanceReference
" After evaluation during 12 h with Ketogan tablets (3-4 dosing intervals), a loading phase lasting for 36 h with cetobem."( Bioavailability and analgesic effect of sustained release cetobemidone capsules in cancer patients with chronic pain of malignant origin.
Andersen, LS; Kjaer, M; Nielsen, H; Olsen, FE; Philipsen, J; Velander, G, 1992
)
0.28
" The patients were six days in hospital and were dosed two days with tablets, two days with mixture and finally another two days with tablets."( Analgesic effect and bioavailability of oral ketogan given as tablets or mixture to patients with chronic pain of malignant origin.
Kjaer, M; Nielsen, H, 1988
)
0.27
" The low oral bioavailability and rapid elimination of ketobemidone demonstrated in this study suggest that the usual dosage recommendation for oral Ketogin (ketobemidone 5--10 mg every 6--7 h) in patients with severe pain is too low."( Clinical pharmacokinetics and oral bioavailability of ketobemidone.
Anderson, P; Arnér, S; Bondesson, U; Boréus, LO; Hartvig, P, 1980
)
0.76
" However, due to the interindividual variability in plasma levels of ketobemidone, independent of phenotype, individual dosing based on the clinical response and therapeutic drug monitoring is recommended."( The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype.
Al-Shurbaji, A; Säwe, J, 2002
)
0.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
piperidines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Ketobemidone Action Pathway3111

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)IC50 (µMol)7.00000.00010.729810.0000AID145930
Delta-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)7.00000.00030.38877.0000AID145930
Kappa-type opioid receptorMus musculus (house mouse)IC50 (µMol)7.00000.00131.538010.0000AID145930
Mu-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)7.00000.00010.887410.0000AID145930
Kappa-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)7.00000.00050.36987.0000AID145930
Mu-type opioid receptorMus musculus (house mouse)IC50 (µMol)7.00000.00081.699210.0000AID145930
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneKappa-type opioid receptorMus musculus (house mouse)
plasma membraneMu-type opioid receptorMus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID127669Compound was evaluated for the hotplate analgesic activity in mouse1992Journal of medicinal chemistry, Oct-02, Volume: 35, Issue:20
Alfred Burger Award address. A half century in medicinal chemistry with major emphasis on pain-relieving drugs and their antagonists.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1123083Analgesic activity in sc dosed mouse by hot plate assay1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
N-(2-Cyanoethyl) derivatives of meperidine, ketobemidone, and a potent 6,7-benzomorphan.
AID151275Ratio between the ED50 values in presence and absence of sodium; value ranges from 7-101992Journal of medicinal chemistry, Oct-02, Volume: 35, Issue:20
Alfred Burger Award address. A half century in medicinal chemistry with major emphasis on pain-relieving drugs and their antagonists.
AID1123082Displacement of radiolabeled dihydromorphine from opioid receptor in rat brain homogenates1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
N-(2-Cyanoethyl) derivatives of meperidine, ketobemidone, and a potent 6,7-benzomorphan.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID145930Tested for displacement of radioligand [3H]-Naloxone from opiate receptor; value ranges from 7-10 uM1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Structure-affinity relationship studies on 5-HT1A receptor ligands. 1. Heterobicyclic phenylpiperazines with N4-alkyl substituents.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID112332Evaluated for analgesic activity in mice using hot plate method1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Some spiro analogues of the potent analgesic ketobemidone.
AID227718Binding energy by using the equation deltaG obsd = -RT ln KD1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Functional group contributions to drug-receptor interactions.
AID151130Compound was evaluated for the inhibition of [3H]naloxone binding to mouse brain homogenate at 1 nM in the presence of 100 mM sodium1992Journal of medicinal chemistry, Oct-02, Volume: 35, Issue:20
Alfred Burger Award address. A half century in medicinal chemistry with major emphasis on pain-relieving drugs and their antagonists.
AID151129Compound was evaluated for the inhibition of [3H]naloxone binding to mouse brain homogenate at 1 nM in the absence of sodium; ED50 = 7-10 nM1992Journal of medicinal chemistry, Oct-02, Volume: 35, Issue:20
Alfred Burger Award address. A half century in medicinal chemistry with major emphasis on pain-relieving drugs and their antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (100)

TimeframeStudies, This Drug (%)All Drugs %
pre-199033 (33.00)18.7374
1990's32 (32.00)18.2507
2000's27 (27.00)29.6817
2010's8 (8.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.61

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.61 (24.57)
Research Supply Index4.87 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index56.46 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.61)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials27 (26.47%)5.53%
Reviews4 (3.92%)6.00%
Case Studies6 (5.88%)4.05%
Observational0 (0.00%)0.25%
Other65 (63.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]