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Drug-Target Interaction

Drug

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PubChem ID:5511
Structure:
Synonyms:
1-Piperidino-2-methyl-3-(p-tolyl)-3-propanone
1-Propanone, 2-methyl-1-(4-methylphenyl)-3-(1-piperidinyl)-
1-Propanone, 2-methyl-1-(4-methylphenyl)-3-(1-piperidinyl)- (9CI)
2,4'-Dimethyl-3-piperidinopropiophenone
2-methyl-1-(4-methylphenyl)-3-(1-piperidinyl)-1-propanone
2-methyl-1-(4-methylphenyl)-3-piperidin-1-ylpropan-1-one
2-methyl-1-(4-methylphenyl)-3-piperidin-1-ylpropan-1-one hydrochloride
2-Methyl-3-piperidino-1-p-tolylpropan-1-one
5-20-02-00357 (Beilstein Handbook Reference)
728-88-1
AC-12150
AC1L1KI7
AC1Q5DU0
AKOS000281128
AR-1J6940
Atmosgen (free base)
BCBcMAP01_000036
Besnoline (free base)
BRD-A27732521-003-02-6
BRN 1285666
BSPBio_003446
C16H23NO
CHEMBL1076211
D08617
DivK1c_000288
EINECS 211-976-4
FSKFPVLPFLJRQB-UHFFFAOYSA-
IDI1_000288
KBio1_000288
KBio2_002506
KBio2_005074
KBio2_007642
KBio3_002666
KBioGR_000772
KBioSS_002514
LS-125220
Menopatol
Mideton
Midocalm
Musclex (TN)
Mydeton
Mydetone
Mydocalm
NCGC00178060-01
NINDS_000288
NSC 107321
NSC107321
PMP
Propiophenone, 2,4'-dimethyl-3-piperidino-
Roystajin (free base)
SPBio_000861
Spectrum2_000851
Spectrum3_001743
Spectrum4_000276
Spectrum5_001115
Spectrum_001960
ST51039048
Tolperisona
Tolperisona [INN-Spanish]
TOLPERISONE
Tolperisone (INN)
Tolperisone [BAN:INN]
Tolperisone [INN:BAN]
Tolperisonum
Tolperisonum [INN-Latin]
WLN: T6NTJ A1Y1&VR D1
ATC-Codes:

Target

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Uniprot ID:CP2CJ_HUMAN
Synonyms:
(R)-limonene 6-monooxygenase
(S)-limonene 6-monooxygenase
(S)-limonene 7-monooxygenase
CYPIIC17
CYPIIC19
Cytochrome P450 2C19
Mephenytoin 4-hydroxylase
P450-11A
P450-254C
EC-Numbers:1.14.13.48
1.14.13.49
1.14.13.80
Organism:Homo sapiens
Human
PDB IDs:-

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----

References:

12695352
Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes.. Balázs Dalmadi; János Leibinger; Szabolcs Szeberényi; Tímea Borbás; Sándor Farkas; Zsolt Szombathelyi; Károly Tihanyi (2003) Drug metabolism and disposition: the biological fate of chemicals display abstract
The in vitro metabolism of tolperisone, 1-(4-methyl-phenyl)-2-methyl-3-(1-piperidino)-1-propanone-hydrochloride, a centrally acting muscle relaxant, was examined in human liver microsomes (HLM) and recombinant enzymes. Liquid chromatography-mass spectrometry measurements revealed methyl-hydroxylation (metabolite at m/z 261; M1) as the main metabolic route in HLM, however, metabolites of two mass units greater than the parent compound and the hydroxy-metabolite were also detected (m/z 247 and m/z 263, respectively). The latter was identified as carbonyl-reduced M1, the former was assumed to be the carbonyl-reduced parent compound. Isoform-specific cytochrome P450 (P450) inhibitors, inhibitory antibodies, and experiments with recombinant P450s pointed to CYP2D6 as the prominent enzyme in tolperisone metabolism. CYP2C19, CYP2B6, and CYP1A2 are also involved to a smaller extent. Hydroxymethyl-tolperisone formation was mediated by CYP2D6, CYP2C19, CYP1A2, but not by CYP2B6. Tolperisone competitively inhibited dextromethorphan O-demethylation and bufuralol hydroxylation (K(i) = 17 and 30 microM, respectively). Tolperisone inhibited methyl p-tolyl sulfide oxidation (K(i) = 1200 microM) in recombinant flavin-containing monooxygenase 3 (FMO3) and resulted in a 3-fold (p < 0.01) higher turnover number using rFMO3 than that of control microsomes. Experiments using nonspecific P450 inhibitors-SKF-525A, 1-aminobenzotriazole, 1-benzylimidazole, and anti-NADPH-P450-reductase antibodies-resulted in 61, 47, 49, and 43% inhibition of intrinsic clearance in HLM, respectively, whereas hydroxymethyl-metabolite formation was inhibited completely by nonspecific chemical inhibitors and by 80% with antibodies. Therefore, it was concluded that tolperisone undergoes P450-dependent and P450-independent microsomal biotransformations to the same extent. On the basis of metabolites formed and indirect evidences of inhibition studies, a considerable involvement of a microsomal reductase is assumed.