ChemFOnt: Showing chemical card for Ketobemidone (CFc000022741)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:11 UTC

Chemfont ID

CFc000022741

Molecule Identification

Common Name

Ketobemidone

Definition

Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted by its metabolite norketobemidone. 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. Ketobemidone is 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. It is usually available as the hydrochloride, which is a white powder. It is synthesized by alkylating (3-methoxyphenyl)acetonitrile with bis(2-chloroethyl)methylamine, followed by reaction with ethylmagnesiumbromide, and finally O-demethylation with hydrobromic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ketodur	HMDB
Cetobemidone	HMDB
Cliradon	HMDB
Ketogan	HMDB
Cymidon	HMDB
Ketorax	HMDB
1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanone	HMDB
1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone	HMDB
4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketone	HMDB
4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidine	HMDB
a 21 Lundbeck	HMDB
Cetobemidon	HMDB
Cliradone	HMDB
Ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketone	HMDB
Ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketone	HMDB
Ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidyl	HMDB
{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}	HMDB
Ketobemidone hydrochloride	HMDB

Chemical Formula

C₁₅H₂₁NO₂

Average Molecular Weight

247.3327

Monoisotopic Molecular Weight

247.157228921

IUPAC Name

1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one

Traditional Name

ketobemidone

CAS Registry Number

469-79-4

SMILES

CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1

InChI Identifier

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

InChI Key

ALFGKMXHOUSVAD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Gamma-aminoketone
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:6125 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041913)

Source

Exogenous

Exogenous (HMDB: HMDB0041913)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ketobemidone Action Pathway (PathBank: SMP0000690)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.01 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.49	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.12 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041913

DrugBank ID

DB06738

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9697

KEGG Compound ID

C11792

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketobemidone

METLIN ID

Not Available

PubChem Compound

10101

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Ketobemidone (CFc000022741)

MOL for CFc000022741 (Ketobemidone)

3D MOL for CFc000022741 (Ketobemidone)

3D SDF for CFc000022741 (Ketobemidone)

3D-SDF for CFc000022741 (Ketobemidone)

PDB for CFc000022741 (Ketobemidone)

3D PDB for CFc000022741 (Ketobemidone)

SMILES for CFc000022741 (Ketobemidone)

INCHI for CFc000022741 (Ketobemidone)

Structure for CFc000022741 (Ketobemidone)

3D Structure for CFc000022741 (Ketobemidone)