Carbamazepine-10,11-epoxide
Carbamazepine is an antiepileptic drug which is metabolized by CYP3A4 into carbamazepine-10,11-epoxide. This metabolite is then detoxified by epoxide hydrolase. As carbamazepine-10,11-epoxide has been associated with neurotoxicity. It has a role as a marine xenobiotic metabolite, a drug metabolite and an allergen. It is an epoxide, a member of ureas and a dibenzoazepine
General
Type : Benzazepin, Epoxide, Carboxamide, Azepane
Chemical_Nomenclature : 3-oxa-11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
Canonical SMILES : C1=CC=C2C(=C1)C3C(O3)C4=CC=CC=C4N2C(=O)N
InChI : InChI=1S\/C15H12N2O2\/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17\/h1-8,13-14H,(H2,16,18)
InChIKey : ZRWWEEVEIOGMMT-UHFFFAOYSA-N
Other name(s) : Carbamazepine epoxide || Carbamazepine 10,11-epoxide || 10,11-Epoxycarbamazepine || CHEBI:3388 || CHEMBL1258 || SCHEMBL156675
MW : 252.27
Formula : C15H12N2O2
CAS_number : 36507-30-9
PubChem : 2555
UniChem : ZRWWEEVEIOGMMT-UHFFFAOYSA-N
Target
Structures : No structure
Families : Epoxide_hydrolase
References (15)
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| Author(s) : Fuhr LM , Marok FZ , Hanke N , Selzer D , Lehr T |
| Ref : Pharmaceutics , 13 :270 , 2021 |
| Abstract : |
| PubMedSearch : Fuhr_2021_Pharmaceutics_13_270 |
| PubMedID: 33671323 |
| Title : Evaluation of clinical and genetic factors in the population pharmacokinetics of carbamazepine - Yip_2021_Br.J.Clin.Pharmacol_87_2572 |
| Author(s) : Yip VLM , Pertinez H , Meng X , Maggs JL , Carr DF , Park BK , Marson AG , Pirmohamed M |
| Ref : British Journal of Clinical Pharmacology , 87 :2572 , 2021 |
| Abstract : |
| PubMedSearch : Yip_2021_Br.J.Clin.Pharmacol_87_2572 |
| PubMedID: 33217013 |
| Title : Different EPHX1 methylation levels in promoter area between carbamazepine-resistant epilepsy group and carbamazepine-sensitive epilepsy group in Chinese population - Lv_2019_BMC.Neurol_19_114 |
| Author(s) : Lv Y , Zheng X , Shi M , Wang Z , Cui L |
| Ref : BMC Neurol , 19 :114 , 2019 |
| Abstract : |
| PubMedSearch : Lv_2019_BMC.Neurol_19_114 |
| PubMedID: 31164100 |
| Title : Association between EPHX1 polymorphisms and carbamazepine metabolism in epilepsy: a meta-analysis - Zhao_2019_Int.J.Clin.Pharm_41_1414 |
| Author(s) : Zhao GX , Shen ML , Zhang Z , Wang P , Xie CX , He GH |
| Ref : Int J Clin Pharm , 41 :1414 , 2019 |
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| PubMedSearch : Zhao_2019_Int.J.Clin.Pharm_41_1414 |
| PubMedID: 31650507 |
| Title : Prediction of drug-drug interactions with carbamazepine-10,11-epoxide using a new in vitro assay for epoxide hydrolase inhibition - Rosa_2016_Xenobiotica_46_1076 |
| Author(s) : Rosa M , Bonnaillie P , Chanteux H |
| Ref : Xenobiotica , 46 :1076 , 2016 |
| Abstract : |
| PubMedSearch : Rosa_2016_Xenobiotica_46_1076 |
| PubMedID: 26936324 |
| Title : Polymorphic Variants of SCN1A and EPHX1 Influence Plasma Carbamazepine Concentration, Metabolism and Pharmacoresistance in a Population of Kosovar Albanian Epileptic Patients - Daci_2015_PLoS.One_10_e0142408 |
| Author(s) : Daci A , Beretta G , Vllasaliu D , Shala A , Govori V , Norata GD , Krasniqi S |
| Ref : PLoS ONE , 10 :e0142408 , 2015 |
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| PubMedID: 26555147 |
| Title : Haplotype structures of EPHX1 and their effects on the metabolism of carbamazepine-10,11-epoxide in Japanese epileptic patients - Nakajima_2005_Eur.J.Clin.Pharmacol_61_25 |
| Author(s) : Nakajima Y , Saito Y , Shiseki K , Fukushima-Uesaka H , Hasegawa R , Ozawa S , Sugai K , Katoh M , Saitoh O , Ohnuma T , Kawai M , Ohtsuki T , Suzuki C , Minami N , Kimura H , Goto Y , Kamatani N , Kaniwa N , Sawada J |
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| Abstract : |
| PubMedSearch : Nakajima_2005_Eur.J.Clin.Pharmacol_61_25 |
| PubMedID: 15692831 |
| Title : Elevation of carbamazepine-10,11-epoxide by quetiapine - Fitzgerald_2002_Pharmacotherapy_22_1500 |
| Author(s) : Fitzgerald BJ , Okos AJ |
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| PubMedSearch : Fitzgerald_2002_Pharmacotherapy_22_1500 |
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| Title : Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene - Kitteringham_1996_J.Pharmacol.Exp.Ther_278_1018 |
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| PubMedSearch : Kitteringham_1996_J.Pharmacol.Exp.Ther_278_1018 |
| PubMedID: 8819481 |
| Title : Carbamazepine-valnoctamide interaction in epileptic patients: in vitro\/in vivo correlation - Pisani_1993_Epilepsia_34_954 |
| Author(s) : Pisani F , Haj-Yehia A , Fazio A , Artesi C , Oteri G , Perucca E , Kroetz DL , Levy RH , Bialer M |
| Ref : Epilepsia , 34 :954 , 1993 |
| Abstract : |
| PubMedSearch : Pisani_1993_Epilepsia_34_954 |
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| Title : In vivo and in vitro correlation of microsomal epoxide hydrolase inhibition by progabide - Kroetz_1993_Clin.Pharmacol.Ther_54_485 |
| Author(s) : Kroetz DL , Loiseau P , Guyot M , Levy RH |
| Ref : Clinical Pharmacology & Therapeutics , 54 :485 , 1993 |
| Abstract : |
| PubMedSearch : Kroetz_1993_Clin.Pharmacol.Ther_54_485 |
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| Title : Measurement of in vivo microsomal epoxide hydrolase activity in white subjects - Kroetz_1993_Clin.Pharmacol.Ther_53_306 |
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| Ref : Clinical Pharmacology & Therapeutics , 53 :306 , 1993 |
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| Title : Heterologous expression of human microsomal epoxide hydrolase in Saccharomyces cerevisiae. Study of the valpromide-carbamazepine epoxide interaction - Eugster_1991_Biochem.Pharmacol_42_1367 |
| Author(s) : Eugster HP , Sengstag C , Hinnen A , Meyer UA , Wurgler FE |
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| Title : Inhibition of human liver microsomal epoxide hydrolase by valproate and valpromide: in vitro\/in vivo correlation - Kerr_1989_Clin.Pharmacol.Ther_46_82 |
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| Abstract : |
| PubMedSearch : Kerr_1989_Clin.Pharmacol.Ther_46_82 |
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| Title : Altered ratio of carbamazepine-10,11-epoxide\/carbamazepine in plasma of children: evidence of anticonvulsant drug interaction - Schoeman_1984_Dev.Med.Child.Neurol_26_749 |
| Author(s) : Schoeman JF , Elyas AA , Brett EM , Lascelles PT |
| Ref : Dev Med Child Neurol , 26 :749 , 1984 |
| Abstract : |
| PubMedSearch : Schoeman_1984_Dev.Med.Child.Neurol_26_749 |
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