Details of the Drug

General Information of Drug (ID: DMM3L6Z)

Drug Name

Ketobemidone

Synonyms

Ketobemidone hydrochloride; Cliradon hydrochloride; Ketobimedon hydrochloride; UNII-U9U6LTV80K; 5965-49-1; EINECS 227-749-8; U9U6LTV80K; 1-Methyl-4-(m-hydroxyphenyl)piperidine-4-ethylketone hydrochloride; Ketobemidone HCl; 1-Propanone, 1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-, hydrochloride; Ketogan (TN); AC1L2YOJ; 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one hydrochloride(1:1); AC1Q5G7W; SCHEMBL9706814; 469-79-4 (Parent); DTXSID00208327; LS-123062; D08101

Indication

Disease Entry	ICD 11	Status	REF
Pain	MG30-MG3Z	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

247.33

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 34% []
Clearance: The drug present in the plasma can be removed from the body at the rate of 9.2 mL/min/kg [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.42 +/- 0.41 hours [2]
Metabolism: The drug is metabolized via the conjugation of the phenolic hydroxyl group, and by N-desmethylation []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.4654 micromolar/kg/day [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.48 L/kg [2]

Chemical Identifiers

Formula: C15H21NO2
IUPAC Name: 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
Canonical SMILES: CCC(=O)C1(CCN(CC1)C)C2=CC(=CC=C2)O
InChI: 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
InChIKey: ALFGKMXHOUSVAD-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 10101
ChEBI ID: CHEBI:6125
CAS Number: 469-79-4
DrugBank ID: DB06738
TTD ID: D04BCW
INTEDE ID: DR0905

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Opioid receptor (OPR)	TTN4QDT	NOUNIPROTAC	Modulator	[4]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[5]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[5]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[5]
Cytochrome P450 2B6 (CYP2B6)	DEPKLMQ	CP2B6_HUMAN	Substrate	[5]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[5]
Prostaglandin G/H synthase 1 (COX-1)	DE073H6	PGH1_HUMAN	Substrate	[6]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4	The mu1 and mu2 opioid receptor binding of ketobemidone, norketobemidone and 3-dimethylamino-1,1-diphenylbutene. Pharmacol Toxicol. 1996 Aug;79(2):103-4.
5	Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96.
6	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.