Basic information
- CAS
469-79-4- Standard SMILES
CCC(=O)C1(c2cccc(O)c2)CCN(C)CC1- InChIKey
ALFGKMXHOUSVAD-UHFFFAOYSA-N- Molecular formula
- C15H21NO2
- Average molar mass
- 247.33 g/mol
- Monoisotopic mass
- 247.15722891
Overview
Ketobemidone is a member of piperidines.
Names & identifiers
- Preferred name
- Ketobemidone
- IUPAC
- 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
- English name
- ketobemidone
- Molecular formula
- C15H21NO2
- Molecular weight
- 247.33
Names & synonyms
KetobemidoneCetobemidoneCliradoneCliradonA 21 LundbeckCetobemidonCiba 7115469-79-4CetobemidonaCetobemidonumChetobemidone1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
Show more names
K 4710K 4710-d3NSC 117863Ciba 7115-d3
4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidinePQS1L514CF1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanoneNSC-117863IDS-NK-001IDS-NK-001(SECT.3)1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone1-(4-(3-Hydroxyphenyl)-1-methyl-4-piperidinyl)-1-propanone
Database identifiers
- CAS
469-79-4- PubChem CID
- 10101
- DTXSID
DTXSID00196977- ChEMBL
CHEMBL47072- ChEBI
CHEBI:6125- UNII
- PQS1L514CF
- EC Number
- 207-421-0
- Nikkaji
- J5.929C
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 295
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule I Controlled Substance -> Opiates
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
LogP1.0
Melting Point156.5 °C
Physical DescriptionSolid
Collision Cross Section159.7 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 156 · 156-157°
- Boiling point
- 390.37 °C · 390.37°C (rough estimate)
- Density
- 1.0267 · 1.0267 (rough estimate)
- refractive index
- 1.513 · 1.5130 (estimate)
- solubility
- Freely soluble in water, soluble in ethanol (96 per cent), very slightly soluble in methylene chloride.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. It also has some NMDA-antagonist properties. This makes it useful for some types of pain that don't respond well to other opioids. 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.
Biological Half-LifePlasma half-life: 2.42 +/- 0.41 h (m +/- SD). Elimination half-life: 3.27 +/- 0.32 h
Metabolism/Metabolites
Ketobemidone is mainly metabolised by conjugation of the phenolic hydroxyl group, and by N-desmethylation. Only about 13-24% is excreted unchanged after iv. administration.
Ketobemidone has known human metabolites that include Ketobemidone O-glucuronide, Norketobemidone, and Ketobemidone sulfate.
MeSH Pharmacological Classification
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.
Absorption, Distribution and Excretion34% (oral), 44% (rectal)
Cellular LocationsMembrane
Metabolite PathwaysKetobemidone Action Pathway
Applications
Usesketobemidone is an opioid analgesic. Used as a substitute to morphine for postoperative pain in children.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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