Methylphenobarbital (BioDeep_00000002731)

 

Secondary id: BioDeep_00001868112

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

化学式: C13H14N2O3 (246.1004)
中文名称: 甲基苯巴比妥
谱图信息: 最多检出来源 Mus musculus(urine) 23.68%

分子结构信息

SMILES: CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1
InChI: InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)

描述信息

Methylphenobarbital is only found in individuals that have used or taken this drug. It is a barbiturate that is metabolized to phenobarbital. It has been used for similar purposes, especially in epilepsy, but there is no evidence mephobarbital offers any advantage over phenobarbital. [PubChem]Methylphenobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives
N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics > N03AA - Barbiturates and derivatives
C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate
D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants

同义名列表

27 个代谢物同义名

5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione; 5-Ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trione; Sanofi synthelabo brand OF mephobarbital; 5-Ethyl-1-methyl-5-phenylbarbituric acid; 5-Ethyl-1-methyl-5-phenylbarbitic acid; N-Methylethylphenylbarbituric acid; 5-Ethyl-1-methyl-5-phenylbarbitate; N-Ethylmethylphenylbarbituric acid; Sanofi brand OF mephobarbital; Methylphenylbarbituric acid; N-Methylphenolbarbitol; N-Methylphenobarbital; Methylphenobarbitalum; Methylphenobarbitonum; 1-Methylphenobarbital; Methyl phenobarbitone; Methylphenolbarbital; Methylphenobarbitone; Methylphenobarbital; Metilfenobarbitale; Metilfenobarbital; Mephobarbitone; Mephobarbital; Prominal; Mebaral; Mephobarbital



数据库引用编号

16 个数据库交叉引用编号

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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 CA1, CYP1A1, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4, FABP1, PTP4A2
Peripheral membrane protein 3 CYP1A1, CYP2B6, CYP2E1
Endosome membrane 1 CLCN5
Endoplasmic reticulum membrane 10 CYP1A1, CYP1A2, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Nucleus 3 FABP1, NR1I2, PTP4A2
cytosol 4 CA1, CLCN5, FABP1, PTP4A2
dendrite 1 ADORA3
nuclear body 1 NR1I2
nucleoplasm 2 FABP1, NR1I2
Cell membrane 2 ADORA3, CLCN5
Multi-pass membrane protein 2 ADORA3, CLCN5
Golgi apparatus membrane 1 CLCN5
Synapse 1 ADORA3
Golgi apparatus 1 CLCN5
Golgi membrane 2 CLCN5, INS
lysosomal membrane 1 CLCN5
mitochondrial inner membrane 3 CYP1A1, CYP2E1, OTC
presynaptic membrane 1 ADORA3
synaptic vesicle 1 CLCN5
plasma membrane 8 ADORA3, CLCN5, CYP2C19, CYP2C8, CYP2C9, ICAM3, PRSS27, PTP4A2
Membrane 5 CLCN5, CYP2A6, CYP2D6, CYP3A4, ICAM3
extracellular exosome 3 CA1, FABP1, ICAM3
endoplasmic reticulum 1 CYP2D6
extracellular space 1 INS
Schaffer collateral - CA1 synapse 1 ADORA3
mitochondrion 3 CYP1A1, CYP2D6, OTC
protein-containing complex 1 FABP1
intracellular membrane-bounded organelle 10 CYP1A1, CYP1A2, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Microsome membrane 7 CYP1A1, CYP1A2, CYP2B6, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Single-pass type I membrane protein 1 ICAM3
Secreted 1 INS
extracellular region 2 INS, PRSS27
Single-pass membrane protein 1 CYP2D6
Mitochondrion matrix 1 OTC
mitochondrial matrix 1 OTC
transcription regulator complex 1 NR1I2
Early endosome 2 CLCN5, PTP4A2
apical part of cell 1 CLCN5
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
peroxisomal matrix 1 FABP1
chromatin 1 NR1I2
endosome lumen 1 INS
intermediate filament cytoskeleton 1 NR1I2
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
cytoplasmic microtubule 1 CYP2A6
apical cortex 1 FABP1


文献列表

  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Nishikant Wase, Boqiang Tu, James W Allen, Paul N Black, Concetta C DiRusso. Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae. Plant physiology. 2017 Aug; 174(4):2146-2165. doi: 10.1104/pp.17.00433. [PMID: 28652262]
  • Offie P Soldin, Sarah H Chung, Donald R Mattison. Sex differences in drug disposition. Journal of biomedicine & biotechnology. 2011; 2011(?):187103. doi: 10.1155/2011/187103. [PMID: 21403873]
  • Bin Wang, Jun He, Shahab A Shamsi. A high-throughput multivariate optimization for the simultaneous enantioseparation and detection of barbiturates in micellar electrokinetic chromatography-mass spectrometry. Journal of chromatographic science. 2010 Aug; 48(7):572-83. doi: 10.1093/chromsci/48.7.572. [PMID: 20819283]
  • Kaoru Kobayashi, Jun Morita, Kan Chiba, Atsuko Wanibuchi, Miyuki Kimura, Shin Irie, Akinori Urae, Takashi Ishizaki. Pharmacogenetic roles of CYP2C19 and CYP2B6 in the metabolism of R- and S-mephobarbital in humans. Pharmacogenetics. 2004 Aug; 14(8):549-56. doi: 10.1097/01.fpc.0000114764.78957.22. [PMID: 15284537]
  • A Ceccato, B Boulanger, P Chiap, P Hubert, J Crommen. Simultaneous determination of methylphenobarbital enantiomers and phenobarbital in human plasma by on-line coupling of an achiral precolumn to a chiral liquid chromatographic column. Journal of chromatography. A. 1998 Sep; 819(1-2):143-53. doi: 10.1016/s0021-9673(98)00547-0. [PMID: 9781418]
  • S Eto, H Noda, A Noda. Chiral separation of barbiturates and hydantoins by reversed-phase high-performance liquid chromatography using a 25 or 50 mm short ODS cartridge column via beta-cyclodextrin inclusion complexes. Journal of chromatography. 1992 Sep; 579(2):253-8. doi: 10.1016/0378-4347(92)80389-8. [PMID: 1429972]
  • M J Eadie. Formation of active metabolites of anticonvulsant drugs. A review of their pharmacokinetic and therapeutic significance. Clinical pharmacokinetics. 1991 Jul; 21(1):27-41. doi: 10.2165/00003088-199121010-00003. [PMID: 1914340]
  • C M Lander, M J Eadie. Plasma antiepileptic drug concentrations during pregnancy. Epilepsia. 1991 Mar; 32(2):257-66. doi: 10.1111/j.1528-1157.1991.tb05253.x. [PMID: 2004630]
  • W H Soine, P J Soine, S E Mongrain, T M England. Stereochemical characterization of the diastereomers of the phenobarbital N-beta-D-glucose conjugate excreted in human urine. Pharmaceutical research. 1990 Apr; 7(4):402-6. doi: 10.1023/a:1015831725205. [PMID: 2362916]
  • N J O'Shea, W D Hooper. Enantioselective binding of mephobarbital to plasma proteins. Chirality. 1990; 2(4):257-62. doi: 10.1002/chir.530020411. [PMID: 2083148]
  • W H Lim, W D Hooper. Stereoselective metabolism and pharmacokinetics of racemic methylphenobarbital in humans. Drug metabolism and disposition: the biological fate of chemicals. 1989 Mar; 17(2):212-7. doi: NULL. [PMID: 2565213]
  • L Grauel, M Almanza, R Alvarez, D Garcia, I Gonzales, I Grimmer, I Körner. Induction of bilirubin-eliminating processes by methylphenobarbital in mature newborn babies. Journal of perinatal medicine. 1988; 16(5-6):431-5. doi: 10.1515/jpme.1988.16.5-6.431. [PMID: 3241289]
  • R S Young, P M Alger, L Bauer, D Lauderbaugh. A randomized, double-blind, crossover study of phenobarbital and mephobarbital. Journal of child neurology. 1986 Oct; 1(4):361-3. doi: 10.1177/088307388600100408. [PMID: 3298402]
  • E Jacqz, S D Hall, R A Branch, G R Wilkinson. Polymorphic metabolism of mephenytoin in man: pharmacokinetic interaction with a co-regulated substrate, mephobarbital. Clinical pharmacology and therapeutics. 1986 Jun; 39(6):646-53. doi: 10.1038/clpt.1986.113. [PMID: 3709029]
  • A Küpfer, R A Branch. Stereoselective mephobarbital hydroxylation cosegregates with mephenytoin hydroxylation. Clinical pharmacology and therapeutics. 1985 Oct; 38(4):414-8. doi: 10.1038/clpt.1985.196. [PMID: 4042524]
  • J Sato, M Nioka, E Owada, K Ito, T Murata. Effect of acetazolamide on the anticonvulsant potency of several antiepileptic drugs in mice. Journal of pharmacobio-dynamics. 1983 May; 6(5):295-300. doi: 10.1248/bpb1978.6.295. [PMID: 6137528]
  • W D Hooper, H E Kunze, M J Eadie. Qualitative and quantitative studies of methylphenobarbital metabolism in man. Drug metabolism and disposition: the biological fate of chemicals. 1981 Jul; 9(4):381-5. doi: NULL. [PMID: 6114839]
  • W D Hooper, H E Kunze, M J Eadie. Simultaneous assay of methylphenobarbital and phenobarbital in plasma using gas chromatography--mass spectrometry with selected ion monitoring. Journal of chromatography. 1981 May; 223(2):426-31. doi: 10.1016/s0378-4347(00)80117-6. [PMID: 7251798]
  • W D Hooper, H E Kunze, M J Eadie. Pharmacokinetics and bioavailability of methylphenobarbital in man. Therapeutic drug monitoring. 1981; 3(1):39-44. doi: 10.1097/00007691-198109000-00004. [PMID: 7233487]
  • H E Kunze, W D Hooper, M J Eadie. High performance liquid chromatographic assay of methylphenobarbital metabolites in urine. Therapeutic drug monitoring. 1981; 3(1):45-9. doi: 10.1097/00007691-198109000-00005. [PMID: 7233488]
  • H J Kupferberg, J Longacre-Shaw. Mephobarbital and phenobarbital plasma concentrations in epileptic patients treated with mephobarbital. Therapeutic drug monitoring. 1979; 1(1):117-22. doi: 10.1097/00007691-197901000-00012. [PMID: 553327]
  • H Kazamatsuri, M Hattori. Serum levels of phenytoin and phenobarbital in epileptic patients treated with mixture antiepileptic tablets, Comital-L or Hydantol-F. Folia psychiatrica et neurologica japonica. 1979; 33(3):319-22. doi: 10.1111/j.1440-1819.1979.tb00763.x. [PMID: 520947]
  • R J Truscott, D G Burke, J Korth, B Halpern, R Summons. Simultaneous determination of diphenylhydantoin, mephobarbital, carbamazepine, phenobarbital and primidone in serum using direct chemical ionization mass spectrometry. Biomedical mass spectrometry. 1978 Aug; 5(8):477-82. doi: 10.1002/bms.1200050803. [PMID: 687779]
  • M J Eadie, F Bochner, W D Hooper, J H Tyrer. Preliminary observations on the pharmacokinetics of methylphenobarbitone. Clinical and experimental neurology. 1978; 15(?):131-44. doi: NULL. [PMID: 756009]
  • M J Eadie, C M Lander, W D Hooper, J H Tyrer. Factors influencing plasma phenobarbitone levels in epileptic patients. British journal of clinical pharmacology. 1977 Oct; 4(5):541-7. doi: 10.1111/j.1365-2125.1977.tb00783.x. [PMID: 911604]
  • L E Mallette. Acetazolamide-accelerated anticonvulsant osteomalacia. Archives of internal medicine. 1977 Aug; 137(8):1013-7. doi: NULL. [PMID: 879939]
  • R M Hill, W M Verniaud, N F Morgan, J Nowlin, L J Glazener, M G Horning. Urinary excretion of phenobarbital in a neonate having withdrawal symptoms. American journal of diseases of children (1960). 1977 May; 131(5):546-50. doi: 10.1001/archpedi.1977.02120180060009. [PMID: 857654]
  • C M Lander, M J Eadie, J H Tyrer. Factors influencing plasma carbamazepine concentrations. Clinical and experimental neurology. 1977; 14(?):184-93. doi: NULL. [PMID: 616596]
  • V Jeremić, R Nikolić. An improved UV-spectrophotometric method for routine barbiturate monitoring. Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie. 1976 Oct; 14(10):479-83. doi: 10.1515/cclm.1976.14.1-12.479. [PMID: 993734]
  • T F Roe, R L Podosin, M E Blaskovics. Drug interaction: diazoxide and diphenylhydantoin. The Journal of pediatrics. 1975 Sep; 87(3):480-4. doi: 10.1016/s0022-3476(75)80665-2. [PMID: 1165531]
  • P Friel, A S Troupin. Flash-heater ethylation of some antiepileptic drugs. Clinical chemistry. 1975 May; 21(6):751-4. doi: . [PMID: 1122620]
  • W Wiegrebe, L Wehrhahn. [Polarographic determination of some phenylsubstituted anticonvulsants]. Arzneimittel-Forschung. 1975 Apr; 25(4):517-24. doi: . [PMID: 1174070]
  • C M Lander, M J Eadie, J H Tyrer. Interactions between anticonvulsants. Proceedings of the Australian Association of Neurologists. 1975; 12(?):111-6. doi: NULL. [PMID: 2912]
  • R M Hill, W M Verniaud, M G Horning, L B McCulley, N F Morgan. Infants exposed in utero to antiepileptic drugs. A prospective study. American journal of diseases of children (1960). 1974 May; 127(5):645-53. doi: 10.1001/archpedi.1974.02110240031002. [PMID: 4825584]
  • J Alvin, M T Bush. The metabolic fate of N,N'-dimethoxymethyl-phenobarbital in the rat. The Journal of pharmacology and experimental therapeutics. 1974 Jan; 188(1):8-14. doi: NULL. [PMID: 4809280]
  • H M Cremers, P E Verheesen. A rapid method for the estimation of anti-epileptic drugs in blood serum by gas-liquid chromatography. Clinica chimica acta; international journal of clinical chemistry. 1973 Nov; 48(4):413-20. doi: 10.1016/0009-8981(73)90420-8. [PMID: 4761589]
  • J W Reynolds, B L Mirkin. Urinary corticosteriod and diphenylhydantoin metabolite patterns in neonates exposed to anticonvulsant drugs in utero. Clinical pharmacology and therapeutics. 1973 Sep; 14(5):891-7. doi: 10.1002/cpt1973145891. [PMID: 4354138]
  • J C Roger, G Rodgers, A Soo. Simultaneous determination of carbamazapine ('Tegretol') and other anticonvulsants in human plasma by gas-liquid chromatography. Clinical chemistry. 1973 Jun; 19(6):590-2. doi: 10.1093/clinchem/19.6.590. [PMID: 4705176]
  • D J Harvey, L Glazener, C Stratton, J Nowlin, R M Hill, M G Horning. Detection of a 5-(3,4-dihydroxy-1,5-cyclohexadien-1-yl)-metabolite of phenobarbital and mephobarbital in rat, guinea pig and human. Research communications in chemical pathology and pharmacology. 1972 May; 3(3):557-65. doi: NULL. [PMID: 5034514]
  • J G MILLICHAP, J D JONES. ACID-BASE, ELECTROLYTE, AND AMINO-ACID METABOLISM IN CHILDREN WITH PETIT MAL. ETIOLOGIC SIGNIFICANCE AND MODIFICATION BY ANTICONVULSANT DRUGS AND THE KETOGENIC DIET. Epilepsia. 1964 Sep; 5(?):239-55. doi: 10.1111/j.1528-1157.1964.tb03331.x. [PMID: 14232248]