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Drug-Target Interaction

Drug

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PubChem ID:37175
Structure:
Synonyms:
( or -)-1-(2-(2,4-dichlorophenylethyl)-2-(2-propenyloxy)ethyl)-1h-imidazole
( or -)-1-(beta-allyloxy-2,4-dichlorophenylethyl)imidazole
(+ or
(+ or -)-1-(2-(2,4-dichlorophenylethyl)-2-(2-propenyloxy)ethyl)-1H-imidazole
(+ or -)-1-(beta-allyloxy-2,4-dichlorophenylethyl)imidazole
(+)-1-(beta-(allyloxy)-2,4-dichlorophenethyl)-imidazole
(+-)-1-(beta-(Allyloxy)-2,4-dichlorophenethyl)-imidazole
1-(2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl)- 1H-imidazole
1-(2-(2,4-Dichlorophenyl)-2-(2-propenyloxy)ethyl)-1H-imidazole
1-(2-(2,4-Dichlorphenyl)-2-(2-propenyloxy)aethyl)-1H-imidazol [German]
1-(2-(Allyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
1-[2-(2,4-dichlorophenyl)-2-prop-2-enoxyethyl]imidazole
1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl)-
1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl)- (9CI)
1h-imidazole, 1-(2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl)-, (+)-
1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl)-, (+-)-
1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-
33586-66-2
33586-66-2 (NITRATE)
35554-44-0
5-23-04-00320 (Beilstein Handbook Reference)
58594-72-2
AB00513978
AIDS-108744
AIDS108744
Allyl-1-(2,4-dichlorophenyl)-2-imidazol-1-ylethyl ether
BPBio1_001063
BRN 0545683
BSPBio_000965
C017435
C14H14Cl2N2O
Caswell No. 497AB
CGA 41333
Chloramizol
D03997
Deccozil
Deccozil S 75
EINECS 252-615-0
Enilconazol
Enilconazole
Enilconazole (BPC)
Enilconazole (USAN/INN)
Enilconazole [USAN:BAN:INN]
Eniloconazol (SP)
EPA Pesticide Chemical Code 111901
Fungaflor
HSDB 6672
Imaverol
IMAZALIL
imazalil mononitrate
imazalil phosphate
imazalil sulfate
imazalil sulfate (1:1)
Imazalil [ANSI:BSI:ISO]
LS-78411
MLS002154075
NCGC00163778-01
NCGC00163778-02
NCGC00163778-03
NCGC00163778-04
NSC187790 (NITRATE)
Prestwick0_000963
Prestwick1_000963
Prestwick2_000963
Prestwick3_000963
R 23979
R-23979
SMR000777988
SPBio_002886

Target

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Uniprot ID:CP1A1_HUMAN
Synonyms:
CYPIA1
Cytochrome P450 1A1
P450 form 6
P450-C
P450-P1
EC-Numbers:1.14.14.1
Organism:Homo sapiens
Human
PDB IDs:-

Binding Affinities:

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

References:

19070657
CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides.. Thérèse Sergent; Isabelle Dupont; Coralie Jassogne; Laurence Ribonnet; Edwige van der Heiden; Marie-Louise Scippo; Marc Muller; Dan McAlister; Luc Pussemier; Yvan Larondelle; Yves-Jacques Schneider (2009) Toxicology letters display abstract
Imazalil (IMA) is a widely used imidazole-antifungal pesticide and, therefore, a food contaminant. This compound is also used as a drug (enilconazole). As intestine is the first site of exposure to ingested drugs and pollutants, we have investigated the effects of IMA, at realistic intestinal concentrations, on xenobiotic-metabolizing enzymes and efflux pumps by using Caco-2 cells, as a validated in vitro model of the human intestinal absorptive epithelium. For comparison, other conazole fungicides, i.e. ketoconazole, propiconazole and tebuconazole, were also studied. IMA induced cytochrome P450 (CYP) 1A1 activity to the same extent as benzo(a)pyrene (B(a)P) or 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), in a dose- and time-dependent manner. Cell-free aryl hydrocarbon receptor (AhR) binding assay and reporter gene assay suggested that IMA is not an AhR-ligand, implying that IMA-mediated induction should involve an AhR-independent pathway. Moreover, IMA strongly inhibited the CYP3A4 activity in 1,25-vitamin D(3)-induced Caco-2 cells. The other fungicides had weak or nil effects on CYP activities. Study of the apical efflux pump activities revealed that ketoconazole inhibited both P-glycoprotein (Pgp) and multidrug resistance-associated protein 2 (MRP-2) or breast cancer resistance protein (BCRP), whereas IMA and other fungicides did not. Our results imply that coingestion of IMA-contaminated food and CYP3A4- or CYP1A1-metabolizable drugs or chemicals could lead to drug bioavailability modulation or toxicological interactions, with possible adverse effects for human health.