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Literature summary for 1.14.14.1 extracted from
- The participation of human hepatic P450 isoforms, flavin-containing monooxygenases and aldehyde oxidase in the biotransformation of the insecticide fenthion (2008), Toxicol. Appl. Pharmacol., 233, 343-352.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| baculovirus-infected insect cells expressing single c-DNA-derived CYPs | Homo sapiens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| furafylline | CYP1A2, at 0.005 mM fenthion, causes a 30% decrease in fenthion-sulfoxide formation. At 0.1 mM fenthion, CYP1A2 inhibition is not evident. Influences fenthion-oxon formation with a 25% inhibition at 0.005 mM or 0.1 mM fenthion concentrations | Homo sapiens |  |
| methanol | partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzymes | Homo sapiens | |
| additional information | antiCYP2B6 antibodies inhibition at 0.005 mM fenthion is not statistically significant, whereas at 0.1 mM fenthion it significantly inhibits the reaction (1520%). Fenthion-oxon formation is mainly influenced by antiCYP2B6 antibodies, with 59% and 40% inhibition at 0.005 mM and 0.1 mM fenthion, respectively; at 0.005 mM fenthion, antiCYP1A2 antibodies cause the highest inhibition of fenthion-sulfoxide formation (25%); at 0.005 mM fenthion, antiCYP2C9 antibodies cause the highest inhibition of fenthion-sulfoxide formation (20%). At 0.1 mM fenthion, presence of antiCYP2C9 antibodies cause a 28% decrease of formed sulfoxide. Anti2C19 antibodies inhibitions at 0.005 mM fenthion is not statistically significant, whereas at 0.1 mM fenthion it significantly inhibits the reaction (1520%). The presence of troleandomycin and antiCYP3A4 antibodies do not affect fenthion-sulfoxide formation in any of the experimental conditions used | Homo sapiens | |
| sulfaphenazole | CYP2C9, at 0.005 mM fenthion, causes a 30% decrease in fenthion-sulfoxide formation. At 0.01 mM fenthion, causes a 48% decrease of formed sulfoxide. Fenthion-oxon formation is reduced by 30% at 0.1 mM fenthion | Homo sapiens | |
| ticlopidine | CYP2B6 and CYP2C19, 40% loss of sulfoxide formation. Decrease in fenthion-oxon formation by 71% and 64% at 0.005 mM or 0.1 mM fenthion concentrations, respectively, which is mainly attributable to CYP2B6 | Homo sapiens | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0016 | - |
fenthion | desulfuration by recombinant human CYPs to fenthion-oxon | Homo sapiens | |
| 0.0022 | - |
fenthion | sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.0024 | - |
fenthion | CYP2C19, desulfuration by recombinant human CYPs to fenthion-oxon | Homo sapiens | |
| 0.0024 | - |
fenthion | CYP2C19, at pH 7.4 and 37°C | Homo sapiens | |
| 0.0027 | - |
fenthion | desulfuration by recombinant human CYPs to fenthion-oxon | Homo sapiens | |
| 0.0044 | - |
fenthion | CYP2C19, sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.0044 | - |
fenthion | CYP2C19, at pH 7.4 and 37°C | Homo sapiens | |
| 0.006 | - |
fenthion | CYP2C9, sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.006 | - |
fenthion | CYP2C9, at pH 7.4 and 37°C | Homo sapiens | |
| 0.008 | - |
fenthion | CYP1A1, sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.008 | - |
fenthion | CYP1A1, at pH 7.4 and 37°C | Homo sapiens | |
| 0.01 | - |
fenthion | sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.012 | - |
fenthion | CYP2C9, desulfuration by recombinant human CYPs to fenthion-oxon | Homo sapiens | |
| 0.012 | - |
fenthion | CYP2C9, at pH 7.4 and 37°C | Homo sapiens | |
| 0.018 | - |
fenthion-sulfoxide | CYP2C19 | Homo sapiens | |
| 0.089 | - |
fenthion | CYP3A4, desulfuration by recombinant human CYPs to fenthion-oxon | Homo sapiens | |
| 0.089 | - |
fenthion | CYP3A4, at pH 7.4 and 37°C | Homo sapiens | |
| 0.131 | - |
fenthion | CYP3A4, sulfoxidation to fenthion-sulfoxide | Homo sapiens | |
| 0.131 | - |
fenthion | CYP3A4, at pH 7.4 and 37°C | Homo sapiens | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| microsome | - |
Homo sapiens | - |
- |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
- |
- |
| Homo sapiens | P05177 | - |
- |
| Homo sapiens | P10632 | - |
- |
| Homo sapiens | P10635 | - |
- |
| Homo sapiens | P11509 | - |
- |
| Homo sapiens | P20813 | - |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| liver | - |
Homo sapiens | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| fenthion + NADPH + H+ + O2 | - |
Homo sapiens | fenthion-oxon + sulfur + NADP+ + H2O | - |
r | |
| fenthion + NADPH + H+ + O2 | - |
Homo sapiens | fenthion-sulfoxide + NADP+ + H2O | - |
r | |
| fenthion + [reduced NADPH-hemoprotein reductase] + O2 | fenthion-sulfoxide and fenthion-oxon, are formed by some CYPs although at very different levels, depending on the relative CYP hepatic content. Fenthion-oxon formation is favored and at low fenthion concentrations CYP2B6 and CYP1A2 are mainly involved in its formation. At higher levels, a more widespread CYP involvement is evident, as in the case of fenthion-sulfoxide | Homo sapiens | ? | - |
? | |
| fenthion-sulfoxide + [reduced NADPH-hemoprotein reductase] + O2 | CYP1A1, CYP2C9 and CYP3A4 form only traces or negligible levels of fenthion-sulfone | Homo sapiens | fenthion-sulfone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| fenthion-sulfoxide + [reduced NADPH-hemoprotein reductase] + O2 | CYP1A2 forms only traces or negligible levels of fenthion-sulfone | Homo sapiens | fenthion-sulfone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| fenthion-sulfoxide + [reduced NADPH-hemoprotein reductase] + O2 | CYP2B6 forms only traces or negligible levels of fenthion-sulfone | Homo sapiens | fenthion-sulfone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| additional information | CYP2C19 can not form fenthion-oxon-sulfoxide from fenthion-oxon | Homo sapiens | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| CYP1A1 | - |
Homo sapiens |
| CYP1A2 | - |
Homo sapiens |
| CYP2A6 | - |
Homo sapiens |
| CYP2B6 | - |
Homo sapiens |
| CYP2C19 | - |
Homo sapiens |
| CYP2C8 | - |
Homo sapiens |
| CYP2C9 | - |
Homo sapiens |
| CYP2D6 | - |
Homo sapiens |
| CYP2E1 | - |
Homo sapiens |
| CYP3A4 | - |
Homo sapiens |
| cytochrome P450 monooxygenase | - |
Homo sapiens |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| NADPH | - |
Homo sapiens | |
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