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Drug-Target Interaction

Drug

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PubChem ID:667477
Structure:
Synonyms:
(3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
(3e)-3-(Dibenzo[b,E]oxepin-11(6h)-Ylidene)-N,N-Dimethylpropan-1-Amine
(3E)-3-dibenzo[b,e]oxepin-11(6H)-ylidene-N,N-dimethylpropan-1-amine
1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-
11-(3-(Dimethylamino)propylidene)-6H-dibenz(b,e)oxepine
11-(3-Dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin
1668-19-5
5EH
AC1LDI63
BPBio1_000118
BRD-K36616567-003-01-5
BRD-K54462405-003-03-3
BSPBio_000106
C19H21NO
CAS-1229-29-4
CCG-204434
CCRIS 9176
CHEBI:36692
CHEMBL1628227
CHEMBL860
Cidoxepin
Cidoxepin [INN]
Cidoxepina
Cidoxepinum
cis-N-(3-(6H-Dibenz(b,e)oxepin-11-yliden)propyl)-N,N-dimethylamin
DB01142
Dibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine, N,N-dimethyl-
Dibenz(b,e)oxepin-delta(sup 11(6H)),gamma-propylamine, N,N-dimethyl-
DOXEPIN
Doxepin Hcl
Doxepin hydrochloride
Doxepin Hydrochloride,
Doxepin [USAN]
Doxepin, Hydrochloride
Doxepina
Doxepina [INN-Spanish]
Doxepine
Doxepinum
Doxepinum [INN-Latin]
E-DOXEPIN
HSDB 3069
L000699
Lopac-D-4526
Lopac0_000339
LS-174582
LS-61638
MF 10
N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine
NCGC00015344-01
NCGC00015344-02
NCGC00015344-03
NCGC00015344-04
NCGC00024623-01
NCGC00162127-01
Prestwick2_000263
Prestwick3_000263
Quitaxon
Sinequan
Tocris-0508
trans-doxepin
Triadapin
UNII-5ASJ6HUZ7D
Zonalon
ATC-Codes:

Target

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Uniprot ID:CP2C9_HUMAN
Synonyms:
(R)-limonene 6-monooxygenase
(S)-limonene 6-monooxygenase
(S)-limonene 7-monooxygenase
CYPIIC9
Cytochrome P450 2C9
P-450MP
P450 MP-4/MP-8
P450 PB-1
S-mephenytoin 4-hydroxylase
EC-Numbers:1.14.13.48
1.14.13.49
1.14.13.80
Organism:Homo sapiens
Human
PDB IDs:1OG2 1OG5 1R9O
Structure:
1R9O

Binding Affinities:

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

References:

12180536
The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19.. Sebastian Härtter; Gunnel Tybring; Thomas Friedberg; Harald Weigmann; Christoph Hiemke (2002) Pharmaceutical research display abstract
PURPOSE: This study was conducted to identify the cytochrome P450s (CYPs) responsible for the metabolism of the cis- and trans-isomers of the tricyclic antidepressant doxepin to its pharmacologically active N-desmethylmetabolite by in vitro techniques. METHODS: The doxepin N-demethylation was studied by means of pooled human liver microsomes and chemical inhibitors, recombinant human (rh)-CYPs, and geno- and phenotyped human liver microsomes. RESULTS: The N-demethylation of both isomers was inhibited most prominently by tranylcypromine (CYP2C19) to more than 50%. Furafylline (CYP1A2) and sulfaphenazole (CYP2C9) inhibited the N-demethylation to a lesser extent while quinidine (CYP2D6) or troleandomycine (CYP3A4) had no effect. Rh-CYP2C19, -CYP1A2, and -CYP2C9 were able to N-demethylate cis- and trans-doxepin. Only traces of trans-desmethyldoxepin were detectable when CYP3A4 was used. The maximum velocity in the cis- and transdoxepin N-demethylation was significantly (P < 0.05) lower in microsomes with low CYP2C19 activity (345 +/- 44 and 508 +/- 75 pmol/min/ mg protein, respectively) compared to those with high CYP2C19 activity (779 +/- 132 and 1,189 +/- 134 pmollmin/mg). CONCLUSION: The present study demonstrates a significant contribution of the polymorphic CYP2C19 to the N-demethylation of doxepin. CYP2C9 and CYP1A2 play a minor role and CYP3A4 does not contribute substantially.
12360109