methapyrilene (BioDeep_00000002520)
human metabolite blood metabolite natural product
代谢物信息卡片
化学式: C14H19N3S (261.13)
中文名称: 美沙吡林
谱图信息:
最多检出来源 Mus musculus(blood) 80.77%
分子结构信息
SMILES: CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1
InChI: InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3
描述信息
R - Respiratory system > R06 - Antihistamines for systemic use > R06A - Antihistamines for systemic use > R06AC - Substituted ethylene diamines
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist
D018926 - Anti-Allergic Agents
同义名列表
26 个代谢物同义名
N-[2-(dimethylamino)ethyl]-N-[(thiophen-2-yl)methyl]pyridin-2-amine; N,N-Dimethyl-n-pyridin-2-yl-n-(2-thienylmethyl)ethane-1,2-diamine; N,N-Dimethyl-n-2-pyridinyl-n-(2-thienylmethyl)-1,2-ethanediamine; N-(alpha-Pyridyl)-N-(alpha-thenyl)-n,n-dimethylethylenediamine; N-(a-Pyridyl)-N-(a-thenyl)-n,n-dimethylethylenediamine; N-(Α-pyridyl)-N-(α-thenyl)-n,n-dimethylethylenediamine; N,N-Dimethyl-n-pyrid-2-yl-n-2-thenylethylenediamine; 2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine; Thenylpyramine; Methypyrilene; Paradormalene; methapyrilene; Pyrinistol; Pyrinistab; Thionylan; Sleepwell; Thenylene; Histadyl; Lullamin; Pyrathyn; Semikon; Restryl; Rest-ON; Tenalin; Methapyrilene; Methapyrilene
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:6820
- KEGG: C11114
- PubChem: 4098
- HMDB: HMDB0254524
- Metlin: METLIN68855
- DrugBank: DB04819
- ChEMBL: CHEMBL1411979
- Wikipedia: Methapyrilene
- MeSH: Methapyrilene
- CAS: 91-80-5
- PMhub: MS000003162
- PubChem: 13296
- NIKKAJI: J4.348F
- RefMet: Methapyrilene
- KNApSAcK: 6820
- LOTUS: LTS0234278
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)
7 个相关的物种来源信息
- 2759 - Eukaryota: LTS0234278
- 3803 - Fabaceae: LTS0234278
- 9606 - Homo sapiens: -
- 3398 - Magnoliopsida: LTS0234278
- 35493 - Streptophyta: LTS0234278
- 49852 - Thermopsis: LTS0234278
- 58023 - Tracheophyta: LTS0234278
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
- Ian D Wilson, Corey Broeckling, Lee A Gethings, Nyasha C Munjoma, Robert Trengove, Paul D Rainville, Steven K Lai, Giorgis Isaac, Robert S Plumb. Development of a single mobile phase for LC-IM-MS-based discovery lipidomics and metabolic phenotyping: Application to methapyrilene hepatotoxicity in the rat.
Journal of chromatography. A.
2024 Jan; 1714(?):464552. doi:
10.1016/j.chroma.2023.464552
. [PMID: 38113579] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040
. [PMID: 33910017] - Hongyan Ma, Huiyun Liang, Shengxin Cai, Barry R O'Keefe, Susan L Mooberry, Robert H Cichewicz. An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures.
Journal of natural products.
2021 03; 84(3):750-761. doi:
10.1021/acs.jnatprod.0c00946
. [PMID: 33226219] - Markus Slopianka, Anne Herrmann, Mira Pavkovic, Heidrun Ellinger-Ziegelbauer, Rainer Ernst, Angela Mally, Matthias Keck, Bjoern Riefke. Quantitative targeted bile acid profiling as new markers for DILI in a model of methapyrilene-induced liver injury in rats.
Toxicology.
2017 07; 386(?):1-10. doi:
10.1016/j.tox.2017.05.009
. [PMID: 28529062] - Alistair C Leitch, Philip M E Probert, James A Shayman, Stephanie K Meyer, George E N Kass, Matthew C Wright. B-13 progenitor-derived hepatocytes (B-13/H cells) model lipid dysregulation in response to drugs and chemicals.
Toxicology.
2017 07; 386(?):120-132. doi:
10.1016/j.tox.2017.05.014
. [PMID: 28552552] - Svitlana Shpyleva, Kostiantyn Dreval, Aline de Conti, Iryna Kindrat, Stepan Melnyk, Jian Yan, Tao Chen, Frederick A Beland, Igor P Pogribny. Editor's Highlight: Organ-Specific Epigenetic Changes Induced by the Nongenotoxic Liver Carcinogen Methapyrilene in Fischer 344 Rats.
Toxicological sciences : an official journal of the Society of Toxicology.
2017 03; 156(1):190-198. doi:
10.1093/toxsci/kfw242
. [PMID: 28013212] - Sibel Ozden, Neslihan Turgut Kara, Osman Ugur Sezerman, İlknur Melis Durasi, Tao Chen, Goksun Demirel, Buket Alpertunga, J Kevin Chipman, Angela Mally. Assessment of global and gene-specific DNA methylation in rat liver and kidney in response to non-genotoxic carcinogen exposure.
Toxicology and applied pharmacology.
2015 Dec; 289(2):203-12. doi:
10.1016/j.taap.2015.09.023
. [PMID: 26431795] - Mira Pavkovic, Björn Riefke, Heidrun Ellinger-Ziegelbauer. Urinary microRNA profiling for identification of biomarkers after cisplatin-induced kidney injury.
Toxicology.
2014 Oct; 324(?):147-57. doi:
10.1016/j.tox.2014.05.005
. [PMID: 24880025] - Yu Yamaura, Miki Nakajima, Naoyuki Tatsumi, Shingo Takagi, Tatsuki Fukami, Koichi Tsuneyama, Tsuyoshi Yokoi. Changes in the expression of miRNAs at the pericentral and periportal regions of the rat liver in response to hepatocellular injury: comparison with the changes in the expression of plasma miRNAs.
Toxicology.
2014 Aug; 322(?):89-98. doi:
10.1016/j.tox.2014.05.008
. [PMID: 24863736] - Yoko Nishimura, Yuji Morikawa, Chiaki Kondo, Yutaka Tonomura, Ryou Fukushima, Mikinori Torii, Takeki Uehara. Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies.
Journal of applied toxicology : JAT.
2013 Oct; 33(10):1120-30. doi:
10.1002/jat.2867
. [PMID: 23558518] - Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Dec; 40(12):2332-41. doi:
10.1124/dmd.112.047068
. [PMID: 22961681] - Costas Koufaris, Jayne Wright, Richard A Currie, Nigel J Gooderham. Hepatic microRNA profiles offer predictive and mechanistic insights after exposure to genotoxic and epigenetic hepatocarcinogens.
Toxicological sciences : an official journal of the Society of Toxicology.
2012 Aug; 128(2):532-43. doi:
10.1093/toxsci/kfs170
. [PMID: 22584684] - Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Jan; 40(1):130-8. doi:
10.1124/dmd.111.040758
. [PMID: 21965623] - Yu Yamaura, Miki Nakajima, Shingo Takagi, Tatsuki Fukami, Koichi Tsuneyama, Tsuyoshi Yokoi. Plasma microRNA profiles in rat models of hepatocellular injury, cholestasis, and steatosis.
PloS one.
2012; 7(2):e30250. doi:
10.1371/journal.pone.0030250
. [PMID: 22363424] - Suzanne Geenen, Filippos Michopoulos, J Gerry Kenna, Kyle L Kolaja, Hans V Westerhoff, Ian Wilson. HPLC-MS/MS methods for the quantitative analysis of ophthalmic acid in rodent plasma and hepatic cell line culture medium.
Journal of pharmaceutical and biomedical analysis.
2011 Apr; 54(5):1128-35. doi:
10.1016/j.jpba.2010.11.038
. [PMID: 21176868] - M Schug, T Heise, A Bauer, D Storm, M Blaszkewicz, E Bedawy, M Brulport, B Geppert, M Hermes, W Föllmann, K Rapp, L Maccoux, W Schormann, K E Appel, A Oberemm, U Gundert-Remy, J G Hengstler. Primary rat hepatocytes as in vitro system for gene expression studies: comparison of sandwich, Matrigel and 2D cultures.
Archives of toxicology.
2008 Dec; 82(12):923-31. doi:
10.1007/s00204-008-0375-x
. [PMID: 18987846] - R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Jul; 36(7):1385-405. doi:
10.1124/dmd.108.020479
. [PMID: 18426954] - Jacob G Bundy, Jasmin K Sidhu, Faisal Rana, David J Spurgeon, Claus Svendsen, Jodie F Wren, Stephen R Stürzenbaum, A John Morgan, Peter Kille. 'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus.
BMC biology.
2008 Jun; 6(?):25. doi:
10.1186/1741-7007-6-25
. [PMID: 18522721] - Ko Omura, Naoki Kiyosawa, Takeki Uehara, Mitsuhiro Hirode, Toshinobu Shimizu, Toshikazu Miyagishima, Atsushi Ono, Taku Nagao, Tetsuro Urushidani. Gene expression profiling of rat liver treated with serum triglyceride-decreasing compounds.
The Journal of toxicological sciences.
2007 Oct; 32(4):387-99. doi:
10.2131/jts.32.387
. [PMID: 17965553] - J Todd Auman, Jeff Chou, Kevin Gerrish, Qihong Huang, Supriya Jayadev, Kerry Blanchard, Richard S Paules. Identification of genes implicated in methapyrilene-induced hepatotoxicity by comparing differential gene expression in target and nontarget tissue.
Environmental health perspectives.
2007 Apr; 115(4):572-8. doi:
10.1289/ehp.9396
. [PMID: 17450226] - Andrew Craig, James Sidaway, Elaine Holmes, Terry Orton, David Jackson, Rachel Rowlinson, Janice Nickson, Robert Tonge, Ian Wilson, Jeremy Nicholson. Systems toxicology: integrated genomic, proteomic and metabonomic analysis of methapyrilene induced hepatotoxicity in the rat.
Journal of proteome research.
2006 Jul; 5(7):1586-601. doi:
10.1021/pr0503376
. [PMID: 16823966] - Dwight D Flammia, Tara Valouch, Susan Venuti. Tissue distribution of quetiapine in 20 cases in Virginia.
Journal of analytical toxicology.
2006 May; 30(4):287-92. doi:
10.1093/jat/30.4.287
. [PMID: 16803670] - Guido Steiner, Laura Suter, Franziska Boess, Rodolfo Gasser, Maria Cristina de Vera, Silvio Albertini, Stefan Ruepp. Discriminating different classes of toxicants by transcript profiling.
Environmental health perspectives.
2004 Aug; 112(12):1236-48. doi:
10.1289/txg.7036
. [PMID: 15345370] - Qihong Huang, Xidong Jin, Elias T Gaillard, Brian L Knight, Franklin D Pack, James H Stoltz, Supriya Jayadev, Kerry T Blanchard. Gene expression profiling reveals multiple toxicity endpoints induced by hepatotoxicants.
Mutation research.
2004 May; 549(1-2):147-67. doi:
10.1016/j.mrfmmm.2003.12.020
. [PMID: 15120968] - Angela Mally, James Kevin Chipman. Non-genotoxic carcinogens: early effects on gap junctions, cell proliferation and apoptosis in the rat.
Toxicology.
2002 Dec; 180(3):233-48. doi:
10.1016/s0300-483x(02)00393-1
. [PMID: 12393293] - Hisham K Hamadeh, Brian L Knight, Astrid C Haugen, Stella Sieber, Rupesh P Amin, Pierre R Bushel, Raymond Stoll, Kerry Blanchard, Supriya Jayadev, Raymond W Tennant, Michael L Cunningham, Cynthia A Afshari, Richard S Paules. Methapyrilene toxicity: anchorage of pathologic observations to gene expression alterations.
Toxicologic pathology.
2002 Jul; 30(4):470-82. doi:
10.1080/01926230290105712
. [PMID: 12187938] - P J O'Brien, Mark R Slaughter, S R Polley, K Kramer. Advantages of glutamate dehydrogenase as a blood biomarker of acute hepatic injury in rats.
Laboratory animals.
2002 Jul; 36(3):313-21. doi:
10.1258/002367702320162414
. [PMID: 12144742] - G S Ratra, C J Powell, B K Park, J L Maggs, S Cottrell. Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation.
Chemico-biological interactions.
2000 Dec; 129(3):279-95. doi:
10.1016/s0009-2797(00)00253-2
. [PMID: 11137066] - T J Oberly, J C Scheuring, K A Richardson, F C Richardson, M L Garriott. The evaluation of methapyrilene for bacterial mutation with metabolic activation by Aroclor-induced, methapyrilene-induced and noninduced rat-liver S9.
Mutation research.
1993 Apr; 299(2):77-84. doi:
10.1016/0165-1218(93)90084-q
. [PMID: 7680426] - F C Richardson, D M Copple, P I Eacho. Effects of methapyrilene on DNA synthesis in mice and rats following continuous dietary exposure.
Carcinogenesis.
1992 Dec; 13(12):2453-7. doi:
10.1093/carcin/13.12.2453
. [PMID: 1473256] - D W Kelly, C L Holder, W A Korfmacher, W Slikker. Plasma elimination and urinary excretion of methapyrilene in the rat.
Drug metabolism and disposition: the biological fate of chemicals.
1990 Nov; 18(6):1018-24. doi:
NULL
. [PMID: 1981507] - L Hernandez, W Lijinsky. Glutathione and lipid peroxide levels in rat liver following administration of methapyrilene and analogs.
Chemico-biological interactions.
1989; 69(2-3):217-24. doi:
10.1016/0009-2797(89)90079-3
. [PMID: 2564814] - R C Kammerer, D A Schmitz, M A Lampe, K Kloc. The in vivo metabolism of methapyrilene, a hepatocarcinogen, in the rat.
Xenobiotica; the fate of foreign compounds in biological systems.
1988 Jul; 18(7):869-81. doi:
10.3109/00498258809041725
. [PMID: 3176524] - K L Steinmetz, C K Tyson, E F Meierhenry, J W Spalding, J C Mirsalis. Examination of genotoxicity, toxicity and morphologic alterations in hepatocytes following in vivo or in vitro exposure to methapyrilene.
Carcinogenesis.
1988 Jun; 9(6):959-63. doi:
10.1093/carcin/9.6.959
. [PMID: 3370759] - M I Perera, S L Katyal, H Shinozuka. Choline deficient diet enhances the initiating and promoting effects of methapyrilene hydrochloride in rat liver as assayed by the induction of gamma-glutamyltranspeptidase-positive hepatocyte foci.
British journal of cancer.
1987 Dec; 56(6):774-8. doi:
10.1038/bjc.1987.286
. [PMID: 2893639] - H M Reznik-Schüller, M D Reuber. Ultrastructure of liver tumors induced in F344 rats by methapyrilene.
Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer.
1986 Sep; 7(1-2):181-95. doi:
. [PMID: 3025410]
- G Fischer, W Lilienblum, D Ullrich, K W Bock. Immunohistochemical differentiation of gamma-glutamyltranspeptidase in focal lesions and in zone I of rat liver after treatment with chemical carcinogens.
Carcinogenesis.
1986 Sep; 7(9):1405-10. doi:
10.1093/carcin/7.9.1405
. [PMID: 2874897] - M I Perera, S L Katyal, H Shinozuka. Methapyrilene induces membrane lipid peroxidation of rat liver cells.
Carcinogenesis.
1985 Jun; 6(6):925-7. doi:
10.1093/carcin/6.6.925
. [PMID: 4006081] - P T Iype, C D Bucana, S P Kelley. Carcinogenesis by nonmutagenic chemicals: early response of rat liver cells induced by methapyrilene.
Cancer research.
1985 May; 45(5):2184-91. doi:
. [PMID: 2985247]
- D Clive. Mutagenicity in drug development: interpretation and significance of test results.
Regulatory toxicology and pharmacology : RTP.
1985 Mar; 5(1):79-100. doi:
10.1016/0273-2300(85)90022-4
. [PMID: 3991935] - M E Graichen, D A Neptun, J G Dent, J A Popp, T B Leonard. Effects of methapyrilene on rat hepatic xenobiotic metabolizing enzymes and liver morphology.
Fundamental and applied toxicology : official journal of the Society of Toxicology.
1985 Feb; 5(1):165-74. doi:
10.1016/0272-0590(85)90061-2
. [PMID: 2859228] - H C Thompson, C L Holder. Trace analysis of the antihistamines methapyrilene hydrochloride, pyrilamine maleate and triprolidine hydrochloride monohydrate in animal feed, human urine and wastewater by high-performance liquid chromatography and gas chromatography with nitrogen-phosphorus detection.
Journal of chromatography.
1984 Jan; 283(?):251-64. doi:
10.1016/s0021-9673(00)96260-5
. [PMID: 6142898] - W Lijinsky, G M Muschik. Distribution of the liver carcinogen methapyrilene in Fischer rats and its interaction with macromolecules.
Journal of cancer research and clinical oncology.
1982; 103(1):69-73. doi:
10.1007/bf00410307
. [PMID: 6176586] - J S Wold, S A Turnipseed. Toxicology of vancomycin in laboratory animals.
Reviews of infectious diseases.
1981 Nov; 3 suppl(?):S224-9. doi:
10.1093/clinids/3.supplement_2.s224
. [PMID: 7342285] - E P Calandre, N Alferez, K Hassanein, D L Azarnoff. Methapyrilene kinetics and dynamics.
Clinical pharmacology and therapeutics.
1981 Apr; 29(4):527-32. doi:
10.1038/clpt.1981.74
. [PMID: 7471621] - R C Baselt, S Franch. Plasma and urine concentrations of methapyrilene by nitrogen-phosphorus gas-liquid chromatography.
Journal of chromatography.
1980 Aug; 183(2):234-8. doi:
10.1016/s0378-4347(00)81699-0
. [PMID: 7400282] - Y L Chan, W Straus. Influence of the tubular flow rates on the endocytic uptake and the excretion of horseradish peroxidase by rat kidney.
Biochemical and biophysical research communications.
1980 Mar; 93(1):271-7. doi:
10.1016/s0006-291x(80)80276-2
. [PMID: 6769439] - C L Winek, F W Fochtman, W J Trogus, E P Fusia, S P Shanor. Methapyrilene toxicity.
Clinical toxicology.
1977; 11(3):287-94. doi:
10.3109/15563657708989842
. [PMID: 913071] - W Q Sturner, J C Garriott. Comparative toxicology in vitreous humor and blood.
Forensic science.
1975 Aug; 6(1-2):31-9. doi:
10.1016/0300-9432(75)90221-6
. [PMID: 2525] - G BOUNOUS, H B SHUMACKER. Effect of histadyl upon regeneration of the renal capsule.
Surgery.
1962 Aug; 52(?):382-4. doi:
NULL
. [PMID: 13871852]