| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | sulfoxide |
|---|---|
| CAS | 5-[2-(octylsulfinyl)propyl]-1,3-benzodioxole |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 18845175 | Leoni C, Buratti FM, Testai E: The participation of human hepatic P450 isoforms, flavin-containing monooxygenases and aldehyde oxidase in the biotransformation of the insecticide fenthion. Toxicol Appl Pharmacol. 2008 Dec 1;233(2):343-52. Epub 2008 Sep 19. In this study the in vitro human hepatic FEN biotransformation was characterized, identifying the relative contributions of cytochrome P450 (CYPs) and/or flavin-containing monooxygenase (FMOs) by using single c-DNA expressed human enzymes, human liver microsomes and cytosol and CYP/FMO-specific inhibitors. Two major metabolites, FEN-sulfoxide and FEN-oxon (FOX), are formed by some CYPs although at very different levels, depending on the relative CYP hepatic content. |
1(0,0,0,1) | Details |
| 17344101 | Mortensen AS, Arukwe A: Modulation of xenobiotic biotransformation system and hormonal responses in Atlantic salmon (Salmo salar) after exposure to tributyltin (TBT). Comp Biochem Physiol C Toxicol Pharmacol. 2007 Apr;145(3):431-41. Epub 2007 Feb 2. Immunochemical and several cytochrome P450 (CYP)-mediated enzyme activity (ethoxyresorufin: EROD, benzyloxyresorufin: BROD, methoxyresorufin: MROD and pentoxyresorufin: PROD) assays were analyzed. |
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| 19905875 | Nishiya Y, Nakamura K, Okudaira N, Abe K, Kobayashi N, Okazaki O: Effects of organic solvents on the time-dependent inhibition of CYP3A4 by diazepam. Xenobiotica. 2010 Jan;40(1):1-8. The effects of organic solvents, acetonitrile, (DMSO), and which are used to dissolve lipophilic test compounds and cytochrome P450 (P450) substrates, and carried into pre-incubation at 1% (v/v), on time-dependent inhibition of CYP3A4 by diazepam, were evaluated using human liver microsomes (HLM) and recombinant human P450 expressed microsomes (rCYPs). |
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| 18238852 | Hay DC, Zhao D, Fletcher J, Hewitt ZA, McLean D, Urruticoechea-Uriguen A, Black JR, Elcombe C, Ross JA, Wolf R, Cui W: Efficient differentiation of hepatocytes from human embryonic stem cells exhibiting markers recapitulating liver development in vivo. Stem Cells. 2008 Apr;26(4):894-902. Epub 2008 Jan 31. More importantly, the hESC-derived hepatocytes express several members of cytochrome P450 isozymes, and these P450 isozymes are capable of converting the substrates to metabolites and respond to the chemical stimulation. |
1(0,0,0,1) | Details |
| 20043645 | Lu D, Peterson LA: Identification of furan metabolites derived from -cis-2-butene-1,4-dial- cross-links. Chem Res Toxicol. 2010 Jan;23(1):142-51. Previous studies indicate that furan is oxidized to a reactive alpha,beta-unsaturated dialdehyde, cis-2-butene-1,4-dial (BDA), in a reaction catalyzed by cytochrome P450. They include the monoglutathione reaction product, N-[4-carboxy-4-(3-mercapto-1H-pyrrol-1-yl)-1-oxobutyl]- cyclic sulfide, and its downstream metabolite, S-[1-(1,3-dicarboxypropyl)-1H-pyrrol-3-yl] methylthiol, as well as (R)-2-acetylamino-6-(2,5-dihydro-2-oxo-1H-pyrrol-1-yl)-1-hexanoic acid and N-acetyl-S-[1-(5-acetylamino-5-carboxypentyl)-1H-pyrrol-3-yl]- and its sulfoxide. |
1(0,0,0,1) | Details |
| 17344341 | Kammerer B, Scheible H, Albrecht W, Gleiter CH, Laufer S: Pharmacokinetics of ML3403 ({4-[5-(4-fluorophenyl)-2-methylsulfanyl-3H--4-yl]-pyridin-2-yl}-( 1-phenylethyl)-amine), a 4-Pyridinylimidazole-type p38 mitogen-activated protein kinase inhibitor. Drug Metab Dispos. 2007 Jun;35(6):875-83. Epub 2007 Mar 7. In addition, pharmacokinetics of ML3403 were evaluated in male and female Wistar rats after oral gavage, showing a fast and high conversion to its active sulfoxide metabolite ML3603. Incubations were carried out with hepatic microsomes from various species and with recombinant human cytochrome P450 isoenzymes, showing that CYP1A2, CYP2C19, CYP2D6, and CYP3A4 are the prominent enzymes in the metabolism of ML3403. |
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| 18203687 | Bohonowych JE, Zhao B, Timme-Laragy A, Jung D, Di Giulio RT, Denison MS: Newspapers and newspaper ink contain agonists for the ah receptor. . Toxicol Sci. 2008 Apr;102(2):278-90. Epub 2008 Jan 17. In addition, DMSO extracts of printed newspaper induced cytochrome P450 1A associated 7-ethoxyresorufin-O-deethylase activity in zebrafish embryos in vivo. |
1(0,0,0,1) | Details |
| 18385292 | Kanebratt KP, Andersson TB: Evaluation of HepaRG cells as an in vitro model for human drug metabolism studies. Drug Metab Dispos. 2008 Jul;36(7):1444-52. Epub 2008 Apr 2. The expression of cytochrome P450 (P450) enzymes, transporter proteins, and transcription factors was stable in differentiated HepaRG cells over a period of 6 weeks when cultured with DMSO. |
1(0,0,0,1) | Details |
| 19111563 | Lavado R, Rimoldi JM, Schlenk D: Mechanisms of fenthion activation in rainbow trout (Oncorhynchus mykiss) acclimated to hypersaline environments. Toxicol Appl Pharmacol. 2009 Mar 1;235(2):143-52. Epub 2008 Dec 9. Stereochemical evaluation of sulfoxide formation, cytochrome P450 inhibition studies with ketoconazole and immunoblots indicated that CYP3A27 was primarily involved in the enhancement of fenthion activation in hypersaline-acclimated fish with limited contribution of FMO to initial sulfoxidation. |
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| 19460561 | Baldini E, Cursio R, Desousa G, Margara A, Honiger J, Saint-Paul MC, Bayer P, Raimondi V, Rahmani R, Mouiel J, Gugenheim J: Cryopreserved porcine hepatocytes: expression and induction of cytochrome P450, isoform CYP2E1. Transplant Proc. 2009 May;41(4):1367-9. |
2(0,0,0,2) | Details |
| 20090406 | Neis MM, Wendel A, Wiederholt T, Marquardt Y, Joussen S, Baron JM, Merk HF: Expression and induction of cytochrome p450 isoenzymes in human skin equivalents. Skin Pharmacol Physiol. 2010;23(1):29-39. Epub 2010 Jan 14. |
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| 19451401 | Li AP: Evaluation of luciferin-isopropyl acetal as a CYP3A4 substrate for human hepatocytes: effects of organic solvents, cytochrome P450 (P450) inhibitors, and P450 inducers. Drug Metab Dispos. 2009 Aug;37(8):1598-603. Epub 2009 May 18. |
2(0,0,0,2) | Details |
| 18629480 | Lupp A, Glockner R, Etzrodt J, Muller D: Precision-cut liver slices from rats of different ages: basal cytochrome P450-dependent monooxygenase activities and inducibility. Anal Bioanal Chem. 2008 Nov;392(6):1173-84. Epub 2008 Jul 16. |
2(0,0,0,2) | Details |
| 19534515 | Porro CS, Sutcliffe MJ, de Visser SP: Quantum mechanics/molecular mechanics studies on the sulfoxidation of dimethyl sulfide by compound I and compound 0 of cytochrome P450: which is the better oxidant?. J Phys Chem A. 2009 Oct 29;113(43):11635-42. |
2(0,0,0,2) | Details |
| 18617602 | Grondin M, Hamel F, Sarhan F, Averill-Bates DA: Metabolic activity of cytochrome p450 isoforms in hepatocytes cryopreserved with wheat protein extract. Drug Metab Dispos. 2008 Oct;36(10):2121-9. Epub 2008 Jul 10. |
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| 18672911 | Medower C, Wen L, Johnson WW: Cytochrome P450 oxidation of the thiophene-containing anticancer drug 3-[(quinolin-4-ylmethyl)-amino]-thiophene-2-carboxylic acid (4-trifluoromethoxy-phenyl)-amide to an electrophilic intermediate. Chem Res Toxicol. 2008 Aug;21(8):1570-7. Epub 2008 Aug 2. The investigational anticancer agent 3-[(quinolin-4-ylmethyl)-amino]-thiophene-2-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (OSI-930) contains a thiophene moiety that can be oxidized by P450s to an apparent sulfoxide, which can react via Michael-addition to the 5-position of the thiophene ring, as demonstrated by mass spectral characterization of several thioether conjugates of the presumed thiophene S-oxide. |
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| 19124257 | Capece BP, Virkel GL, Lanusse CE: Enantiomeric behaviour of albendazole and fenbendazole sulfoxides in domestic animals: pharmacological implications. Vet J. 2009 Sep;181(3):241-50. Epub 2009 Jan 4. These parent compounds are metabolised to albendazole sulfoxide and fenbendazole sulfoxide (oxfendazole), respectively. Both the flavin-monooxygenase and cytochrome P450 systems are involved in the enantioselective biotransformation of these anthelmintic compounds in ruminant species. |
1(0,0,0,1) | Details |
| 17365614 | Lyssimachou A, Arukwe A: Alteration of brain and interrenal StAR protein, P450scc, and Cyp11beta mRNA levels in atlantic salmon after nominal waterborne exposure to the synthetic pharmaceutical J Toxicol Environ Health A. 2007 Apr 1;70(7):606-13. Recently, it was shown that the documented xenoestrogen nonylphenol produced variations in brain steroidogenic acute regulatory (StAR) protein, cytochrome P-450-mediated side-chain cleavage (P450scc), and cytochrome P-45011beta hydroxylase (CYP11beta) gene transcripts of exposed juvenile salmon (Arukwe, 2005). |
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| 19497421 | Vondracek J, Krcmar P, Prochazkova J, Trilecova L, Gavelova M, Skalova L, Szotakova B, Buncek M, Radilova H, Kozubik A, Machala M: The role of aryl hydrocarbon receptor in regulation of enzymes involved in metabolic activation of polycyclic aromatic hydrocarbons in a model of rat liver progenitor cells. Chem Biol Interact. 2009 Jul 15;180(2):226-37. Epub 2009 Mar 27. The present study aimed to characterize expression/activities of enzymes of two major pathways involved in the metabolism of benzo [a] pyrene (BaP): cytochrome P450 (CYP) family 1 enzymes and cytosolic aldo-keto reductases (AKRs). |
1(0,0,0,1) | Details |
| 19441776 | Lu D, Sullivan MM, Phillips MB, Peterson LA: Degraded protein adducts of cis-2-butene-1,4-dial are urinary and hepatocyte metabolites of furan. Chem Res Toxicol. 2009 Jun;22(6):997-1007. Three additional urinary metabolites of furan were also characterized as follows: R-2-acetylamino-6-(2,5-dihydro-2-oxo-1H-pyrrol-1-yl)-1-hexanoic acid, N-acetyl-S-[1-(5-acetylamino-5-carboxypentyl)-1H-pyrrol-3-yl]- and its sulfoxide. However, the toxicity requires cytochrome P450-catalyzed oxidation of furan. |
1(0,0,0,1) | Details |
| 19219915 | Grondin M, Hamel F, Averill-Bates DA, Sarhan F: Wheat proteins improve cryopreservation of rat hepatocytes. . Biotechnol Bioeng. 2009 Jun 15;103(3):582-91. These improved procedures enhance long-term storage (2-12 months) and recovery of large quantities of healthy cells after cryopreservation, and maintain the differentiated functions of rat hepatocytes, compared to freshly isolated cells, as judged by viability (77-93%), adherence (77%) and metabolic functions of major cytochrome P450 isoforms CYP1A1/2, CYP2C6, CYP2D2, and CYP3A1/2. |
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