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The metabolism of dibenz[b,f]-1,4-oxazepine (CR): in vivo hydroxylation of 10,11-dihydrodibenz[b,f]-1,4-oxazepin-11-(1OH)-one and the NIH shift.

作者信息

Harrison J M, Clarke R J, Inch T D, Upshall D G

出版信息

Experientia. 1978 Jun 15;34(6):698-9. doi: 10.1007/BF01947265.

DOI:10.1007/BF01947265
PMID:658275
Abstract

Studies of the in vivo metabolism of 10,11-dihydrodibenz[b,f]-1,4-oxazepin-11-(1OH)-one (2) specifically deuteriated at C7 implicate an arene oxide intermediate during the conversion to 7-hydroxy-2 (4) as evidenced by the observation of the NIH shift.

摘要

相似文献

1
The metabolism of dibenz[b,f]-1,4-oxazepine (CR): in vivo hydroxylation of 10,11-dihydrodibenz[b,f]-1,4-oxazepin-11-(1OH)-one and the NIH shift.
Experientia. 1978 Jun 15;34(6):698-9. doi: 10.1007/BF01947265.
2
The fate of dibenz[b,f]-1,4-oxazepine (CR) in the rat, rhesus monkey and guinea-pig. Part I. Metabolism in vivo.二苯并[b,f]-1,4-恶唑嗪(CR)在大鼠、恒河猴和豚鼠体内的命运。第一部分。体内代谢
Xenobiotica. 1983 Jun;13(6):345-59. doi: 10.3109/00498258309052273.
3
The fate of dibenz[b,f]-1,4-oxazepine (CR) in the rat. Part III. The intermediary metabolites.二苯并[b,f]-1,4-恶唑嗪(CR)在大鼠体内的代谢情况。第三部分。中间代谢产物。
Xenobiotica. 1983 Jun;13(6):373-81. doi: 10.3109/00498258309052275.
4
Studies on the uptake and metabolism of dibenz(b,f)-1,4-oxazepine (CR) by guinea-pig cornea.豚鼠角膜对二苯并(b,f)-1,4-恶唑嗪(CR)的摄取与代谢研究。
Toxicology. 1978 Feb;9(1-2):11-20. doi: 10.1016/0300-483x(78)90027-6.
5
The fate of dibenz[b,f]-1,4-oxazepine (CR) in the rat. Part II. Metabolism in vitro.二苯并[b,f]-1,4-恶唑嗪(CR)在大鼠体内的命运。第二部分。体外代谢
Xenobiotica. 1983 Jun;13(6):361-72. doi: 10.3109/00498258309052274.
6
GLC determination of 7-chloro-5,11-dihydrodibenz[b,e][1,4]-oxazepine-5-carboxamide in serum or plasma.血清或血浆中7-氯-5,11-二氢二苯并[b,e][1,4] - 恶唑并氮杂卓-5-甲酰胺的葡萄糖测定法。
J Pharm Sci. 1975 Sep;64(9):1531-4. doi: 10.1002/jps.2600640924.
7
Synthetic utilization of polynitroaromatic compounds. 3. Preparation of substituted dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-trinitrobenzoic acid via nucleophilic displacement of nitro groups.
J Org Chem. 2005 Nov 11;70(23):9371-6. doi: 10.1021/jo051425c.
8
2-Chloro-11-(1-piperazinyl)dibenz[b, f] [1, 4]oxazepine (amoxapine), an antidepressant with antipsychotic properties--a possible role for 7-hydroxyamoxapine.2-氯-11-(1-哌嗪基)二苯并[b,f][1,4]恶唑平(阿莫沙平),一种具有抗精神病特性的抗抑郁药——7-羟基阿莫沙平的可能作用。
Biochem Pharmacol. 1979 Aug 15;28(16):2514-5. doi: 10.1016/0006-2952(79)90017-0.
9
[On the stability of the irritant dibenz-[b,f]-[1,4]-oxazepine (substance CR)].
Sud Med Ekspert. 2012 May-Jun;55(3):15-8.
10
Physical characterization and activity in vivo of polymorphic forms of 7-chloro-5, 11-dihydrodibenz[b, e][1, 4]oxazepine-5-carboxamide, a potential tricyclic antidepressant.7-氯-5,11-二氢二苯并[b,e][1,4]恶唑并-5-甲酰胺的多晶型物的物理特性及体内活性,一种潜在的三环类抗抑郁药。
J Pharm Sci. 1976 Sep;65(9):1380-5. doi: 10.1002/jps.2600650929.

本文引用的文献

1
The migration of deuterium during aryl hydroxylation. II. Effect of induction of microsomal hydroxylases with phenobarbital or polycyclic aromatic hydrocarbons.
Arch Biochem Biophys. 1969 Apr;131(1):238-44. doi: 10.1016/0003-9861(69)90127-1.
2
Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes. I. Influence of ring substitutents.
Arch Biochem Biophys. 1968 Nov;128(2):517-27. doi: 10.1016/0003-9861(68)90059-3.
3
Biological formation and disposition of arene oxides.芳烃氧化物的生物形成与代谢
Lloydia. 1974 Jun;37(2):212-8.
4
Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds.芳烃氧化物与NIH迁移:芳香族化合物的代谢、毒性及致癌性
Experientia. 1972 Oct 15;28(10):1129-49. doi: 10.1007/BF01946135.
5
Deuterium isotope effects during formation of phenols by hepatic monoxygenases. Evidence for an alternative to arene oxide pathway.肝脏单加氧酶形成酚类过程中的氘同位素效应。芳烃氧化物途径替代途径的证据。
Biochemistry. 1975 May 6;14(9):2024-31. doi: 10.1021/bi00680a033.