Protein Information

Name epoxide hydrolase
Synonyms EPHX; EPHX 1; EPHX1; EPHX1 protein; EPOX; Epoxide hydratase; Epoxide hydrolase; Epoxide hydrolase 1…

Compound Information

Name ethylene oxide
CAS oxirane

Reference List

PubMed Abstract RScore(About this table)
17416773 Haufroid V, Merz B, Hofmann A, Tschopp A, Lison D, Hotz P: Exposure to ethylene oxide in hospitals: biological monitoring and influence of glutathione S-transferase and epoxide hydrolase polymorphisms. Cancer Epidemiol Biomarkers Prev. 2007 Apr;16(4):796-802.

This cross-sectional study aimed at examining (a) whether the urinary excretion of a metabolite of ethylene oxide, 2-hydroxyethyl mercapturic acid (HEMA), could be used for monitoring occupational exposure and (b) whether glutathione S-transferase (GST) and epoxide hydrolase genotypes influenced biological monitoring.
38(0,1,2,3) Details
12767152 Funar-Timofei S, Suzuki T, Paier JA, Steinreiber A, Faber K, Fabian WM: Quantitative structure-activity relationships for the enantioselectivity of oxirane ring-opening catalyzed by epoxide hydrolases. J Chem Inf Comput Sci. 2003 May-Jun;43(3):934-40.

3(0,0,0,3) Details
12926852 Paier J, Stockner T, Steinreiber A, Faber K, Fabian WM: Enantioselectivity of epoxide hydrolase catalysed oxirane ring opening: a 3D QSAR study. J Comput Aided Mol Des. 2003 Jan;17(1):1-11.

3(0,0,0,3) Details
16386346 Godderis L, Aka P, Mateuca R, Kirsch-Volders M, Lison D, Veulemans H: Dose-dependent influence of genetic polymorphisms on DNA damage induced by styrene oxide, ethylene oxide and gamma-radiation. Toxicology. 2006 Feb 15;219(1-3):220-9. Epub 2005 Dec 28.

EPHX1 and GSTs play an important role in the detoxification of electrophiles and oxidative stress.
2(0,0,0,2) Details
15668107 Paulsson B, Rannug A, Henderson AP, Golding BT, Tornqvist M, Warholm M: In vitro studies of the influence of glutathione transferases and epoxide hydrolase on the detoxification of acrylamide and glycidamide in blood. Mutat Res. 2005 Feb 7;580(1-2):53-9.

In a parallel experiment, incubation with ethylene oxide was used as positive control.
2(0,0,0,2) Details
14976339 Himmelstein MW, Carpenter SC, Hinderliter PM: Kinetic modeling of beta-chloroprene metabolism: I. Toxicol Sci. 2004 May;79(1):18-27. Epub 2004 Feb 19.


This study investigated the species-dependent in vitro kinetics of CD oxidation and subsequent 1-CEO metabolism by microsomal epoxide hydrolase and cytosolic glutathione S-transferases in liver and lung, tissues that are prone to tumor induction.
2(0,0,0,2) Details
16288948 Eick JD, Smith RE, Pinzino CS, Kostoryz EL: Stability of silorane dental monomers in aqueous systems. J Dent. 2006 Jul;34(6):405-10. Epub 2005 Nov 9.


Siloranes were mixed in aqueous solutions with and without 1% tetrahydrofuran (THF) containing either liver esterase or epoxide hydrolase at pH 7.4, or dilute HCl at pH 1.4.
2(0,0,0,2) Details
16870169 Munter T, Cottrell L, Ghai R, Golding BT, Watson WP: The metabolism and molecular toxicology of chloroprene. Chem Biol Interact. 2007 Mar 20;166(1-3):323-31. Epub 2006 Jun 3.


Epoxide (2a/2b) was a substrate for mammalian microsomal epoxide hydrolases, which showed preferential hydrolysis of the (S)-enantiomer (2b).
2(0,0,0,2) Details
17193739 Hurst HE: Toxicology of 1,3-butadiene, chloroprene, and isoprene. Rev Environ Contam Toxicol. 2007;189:131-79.

These metabolites are detoxified through hydrolysis by epoxide hydrolase enzymes and through conjugation with glutathione with the aid of glutathione S-transferase.
Melnick and Sills (2001) compared the carcinogenic potentials of these three dienes, along with that of ethylene oxide, which also acts through an epoxide intermediate.
1(0,0,0,1) Details
18175006 Kona J: Theoretical study on the mechanism of a ring-opening reaction of oxirane by the active-site aspartic dyad of HIV-1 protease. Org Biomol Chem. 2008 Jan 21;6(2):359-65. Epub 2007 Dec 6.


Here we also briefly discuss differences between the epoxide ring-opening reaction in HIV-1 protease and epoxide hydrolase, and the accuracy of the DFT method used.
1(0,0,0,1) Details