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]
Affected Organisms
Humans and other mammals
ATC Code
N02AB01: Ketobemidone
N02AB: Phenylpiperidine derivatives
N02A: OPIOIDS
N02: ANALGESICS
N: NERVOUS SYSTEM
N02AB01: Ketobemidone
N02AB: Phenylpiperidine derivatives
N02A: OPIOIDS
N02: ANALGESICS
N: NERVOUS SYSTEM
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) 1
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
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
CHEMBL6125
CAS Number
469-79-4
UNII
PQS1L514CF
DrugBank ID
DB06738
TTD ID
D04BCW
INTEDE ID
DR0905
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

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]
Molecular Interaction Atlas (MIA) 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.