Nirvanol (BioDeep_00000002088)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C11H12N2O2 (204.0899)
中文名称: 5-乙基-5-苯基海因
谱图信息:
最多检出来源 Homo sapiens(blood) 49.35%
分子结构信息
SMILES: CCC1(C(=O)NC(=O)N1)C2=CC=CC=C2
InChI: InChI=1S/C11H12N2O2/c1-2-11(8-6-4-3-5-7-8)9(14)12-10(15)13-11/h3-7H,2H2,1H3,(H2,12,13,14,15)
描述信息
Nirvanol is a metabolite of Mephenytoin. Nirvanol, also known as ethylphenylhydantoin, is a derivative of hydantoin with anticonvulsant properties. Its 5-ethyl-5-phenyl substitution pattern is similar to that of phenobarbital. It is useful in the treatment of chorea. (Wikipedia)
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants
同义名列表
14 个代谢物同义名
2,4-Imidazolidinedione,5-ethyl-5-phenyl-; 5-ethyl-5-phenylimidazolidine-2,4-dione; Ethylphenylhydantoin, 4-(11)C-labeled; Ethylphenylhydantoin, (+-)-isomer; Ethylphenylhydantoin, (R)-isomer; Ethylphenylhydantoin, (S)-isomer; 5-Phenyl-5-ethylhydantoin; 5-Ethyl-5-phenylhydantoin; Desmethylmephenytoin; Ethylphenylhydantoin; Normephenytoin; Nirvanol; Nirvanol; Nirvanol
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:79441
- KEGG: C14916
- PubChem: 91480
- HMDB: HMDB0060533
- Metlin: METLIN70418
- ChEMBL: CHEMBL1438
- Wikipedia: Nirvanol
- chemspider: 82605
- CAS: 2216-93-5
- CAS: 631-07-2
- PMhub: MS000001812
- PubChem: 17395914
- NIKKAJI: J9.448J
- KNApSAcK: 79441
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Tobias Klaassen, Alexander Jetter, Dorota Tomalik-Scharte, Dirk Kasel, Julia Kirchheiner, Ulrich Jaehde, Uwe Fuhr. Assessment of urinary mephenytoin metrics to phenotype for CYP2C19 and CYP2B6 activity.
European journal of clinical pharmacology.
2008 Apr; 64(4):387-98. doi:
10.1007/s00228-007-0416-z. [PMID: 18071681] - Britt Jansson, Doaa Elsherbiny, Ulrika S H Simonsson. Enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4'-hydroxymephenytoin in human plasma and urine by liquid chromatography/tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2006; 20(3):463-72. doi:
10.1002/rcm.2324. [PMID: 16395737] - Tobias Klaassen, Dirk Kasel, Stefanie Harlfinger, Uwe Fuhr. Quantification of mephenytoin and its metabolites 4'-hydroxymephenytoin and nirvanol in human urine using a simple sample processing method.
Rapid communications in mass spectrometry : RCM.
2004; 18(15):1675-80. doi:
10.1002/rcm.1539. [PMID: 15282764] - Britt Jansson, Ulrika S H Simonsson, Michael Ashton. Simultaneous enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4'-hydroxymephenytoin in human plasma by liquid chromatography.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 Jul; 791(1-2):179-91. doi:
10.1016/s1570-0232(03)00221-6. [PMID: 12798178] - R W Nims, J S Sidhu, P E Thomas, D W Mellini, V C Nelson, C J Omiecinski, R A Lubet. Absence of enantioselectivity in the pharmacodynamics of P450 2B induction by 5-ethyl-5-phenylhydantoin in the male rat liver or in cultured rat hepatocytes.
Journal of biochemical toxicology.
1994 Dec; 9(6):279-88. doi:
10.1002/jbt.2570090602. [PMID: 7534352] - R W Nims, R A Lubet, B A Diwan, D W Mellini, W E Utermahlen, P E Thomas. Hepatic cytochrome P450 2B induction by ethyl/phenyl-substituted congeners of phenobarbital in the B6C3F1 mouse.
Journal of biochemical toxicology.
1994 Oct; 9(5):269-78. doi:
10.1002/jbt.2570090507. [PMID: 7853362] - R W Nims, P R Sinclair, J F Sinclair, P E Thomas, C R Jones, D W Mellini, J L Syi, R A Lubet. Pharmacodynamics of cytochrome P450 2B induction by phenobarbital, 5-ethyl-5-phenylhydantoin, and 5-ethyl-5-phenyloxazolidinedione in the male rat liver or in cultured rat hepatocytes.
Chemical research in toxicology.
1993 Mar; 6(2):188-96. doi:
10.1021/tx00032a008. [PMID: 8477010] - I H Hall, J H Maguire, O T Wong, P A Day, R S Alpin. A comparison of the S(+) and R(-) enantiomers of 5-ethyl-5-phenylhydantoin as hypolipidemic agents in rodents.
Biomedica biochimica acta.
1987; 46(7):623-34. doi:
. [PMID: 3426573] - W Kalow. The genetic defect of mephenytoin hydroxylation.
Xenobiotica; the fate of foreign compounds in biological systems.
1986 May; 16(5):379-89. doi:
10.3109/00498258609050246. [PMID: 3739364] - T Inaba, M Jurima, W Kalow. Family studies of mephenytoin hydroxylation deficiency.
American journal of human genetics.
1986 May; 38(5):768-72. doi:
NULL. [PMID: 3717162] - H Fujioka, T Tan, M Kishi, H Miyazaki, Y Masuda, Y Yokoyama. Biopharmaceutical studies on hydantoin derivatives. V. Pharmacokinetics and pharmacodynamics of 5,5-diphenylhydantoin and 1-benzenesulfonyl-5,5-diphenylhydantoin.
Journal of pharmacobio-dynamics.
1986 Mar; 9(3):303-14. doi:
10.1248/bpb1978.9.303. [PMID: 3459864] - W H Theodore, M E Newmark, B T Desai, H J Kupferberg, J K Penry, R J Porter, W D Yonekawa. Disposition of mephenytoin and its metabolite, nirvanol, in epileptic patients.
Neurology.
1984 Aug; 34(8):1100-2. doi:
10.1212/wnl.34.8.1100. [PMID: 6431315] - A Küpfer, R Patwardhan, S Ward, S Schenker, R Preisig, R A Branch. Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans.
The Journal of pharmacology and experimental therapeutics.
1984 Jul; 230(1):28-33. doi:
NULL. [PMID: 6747829] - P J Wedlund, B J Sweetman, C B McAllister, R A Branch, G R Wilkinson. Direct enantiomeric resolution of mephenytoin and its N-demethylated metabolite in plasma and blood using chiral capillary gas chromatography.
Journal of chromatography.
1984 Apr; 307(1):121-7. doi:
10.1016/s0378-4347(00)84078-5. [PMID: 6725478] - J H Maguire, T C Butler, K H Dudley. 5-ethyl-5-phenylhydantoin N-glucuronide, the major urinary metabolite of 5-ethyl-5-phenylhydantoin (Nirvanol) in the dog.
Drug metabolism and disposition: the biological fate of chemicals.
1982 Nov; 10(6):595-8. doi:
. [PMID: 6130906] - R James, A Küpfer, J P Villeneuve, R A Branch. Induction of drug-metabolizing enzymes by the enantiomers of normephenytoin in the rat.
Drug metabolism and disposition: the biological fate of chemicals.
1981 May; 9(3):297-302. doi:
NULL. [PMID: 6113944] - G Karlaganis, A Küpfer, J Bircher, U P Schlunegger, H Gfeller, P Bigler. Identification of mephenytoin metabolites in the dog.
Drug metabolism and disposition: the biological fate of chemicals.
1980 May; 8(3):173-7. doi:
NULL. [PMID: 6104582] - V A Raisys, A M Zebelman, S F MacMillan. Gas-chromatographic determination of mephenytoin and desmethylmephenytoin, after off-column alkylation.
Clinical chemistry.
1979 Jan; 25(1):172-5. doi:
. [PMID: 761360] - A Küpfer, J Bircher, R Preisig. Stereoselective metabolism, pharmacokinetics and biliary elimination of phenylethylhydantoin (Nirvanol) in the dog.
The Journal of pharmacology and experimental therapeutics.
1977 Dec; 203(3):493-9. doi:
NULL. [PMID: 925954]
