3-hydroxymethylantipyrine (BioDeep_00000614871)
Chemicals and Drugs
代谢物信息卡片
5-(hydroxymethyl)-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
化学式: C11H12N2O2 (204.0898732)
中文名称: 5-(羟基甲基)-1-甲基-2-苯基-1H-吡唑-3(2H)-酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1C(=CC(=O)N1C2=CC=CC=C2)CO
InChI: InChI=1S/C11H12N2O2/c1-12-10(8-14)7-11(15)13(12)9-5-3-2-4-6-9/h2-7,14H,8H2,1H3
描述信息
A pyrazolone that is antipyrine in which one of the hydrogens of the 5-methyl group is substituted by a hydroxymethyl group. It is a metabolite of the analgesic drug, antipyrene.
同义名列表
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:145210
- PubChem: 123963
- Metlin: METLIN85279
- CAS: 18125-49-0
- MetaboLights: MTBLC145210
分类词条
相关代谢途径
Reactome(0)
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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)
0 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。
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文献列表
- Yury I Chernyak, Jean A Grassman. Impact of AhRR (565C > G) polymorphism on dioxin dependent CYP1A2 induction.
Toxicology letters.
2020 Mar; 320(?):58-63. doi:
10.1016/j.toxlet.2019.12.002. [PMID: 31805342] - Yury I Chernyak, Alla P Merinova, Andrey A Shelepchikov, Sergey I Kolesnikov, Jean A Grassman. Impact of dioxins on antipyrine metabolism in firefighters.
Toxicology letters.
2016 May; 250-251(?):35-41. doi:
10.1016/j.toxlet.2016.04.006. [PMID: 27067104] - Iu I Cherniak, D A Grassman, A A Shelepchikov. [Markers of impact and effects of dioxines in firemen who participated in fire extinguishing at 'Irkutskcabel' plant].
Meditsina truda i promyshlennaia ekologiia.
2005; ?(12):41-6. doi:
NULL. [PMID: 16430122] - S X Jiang, J E Bayón, I Ferre, X Z Mao, J González-Gallego. Effect of experimental fasciolosis on antipyrine metabolism and clearance in water buffaloes.
Veterinary parasitology.
2000 Mar; 88(3-4):177-86. doi:
10.1016/s0304-4017(99)00217-4. [PMID: 10714456] - J L Mauriz, B Tabernero, J García-López, F Jorquera, J G Villa, J González-Gallego. Physical exercise and improvement of liver oxidative metabolism in the elderly.
European journal of applied physiology.
2000 Jan; 81(1-2):62-6. doi:
10.1007/pl00013798. [PMID: 10552268] - F Jorquera, M Almar, M Pozuelo, D Sansegundo, M González-Sastre, J González-Gallego. The effect of age and sex on metabolism and urinary excretion of antipyrine.
The journals of gerontology. Series A, Biological sciences and medical sciences.
1998 Jan; 53(1):M14-9. doi:
10.1093/gerona/53a.1.m14. [PMID: 9467428] - V L Lanchote, W C Ping, S R Santos. Determination of antipyrine and metabolites in plasma of a patient with mild renal failure.
Therapeutic drug monitoring.
1997 Dec; 19(6):705-10. doi:
10.1097/00007691-199712000-00017. [PMID: 9421115] - K Janus, Z Muszczynski, J Suszycka. Influence of short-term water deprivation on antipyrine disposition in calves.
Research in veterinary science.
1997 Jul; 63(1):1-3. doi:
10.1016/s0034-5288(97)90149-1. [PMID: 9368948] - K Janus, J Suszycka. The effect of cimetidine on antipyrine metabolism in calves.
Journal of veterinary pharmacology and therapeutics.
1997 Feb; 20(1):73-6. doi:
10.1046/j.1365-2885.1997.00040.x. [PMID: 9049953] - K Janus, Z Muszczynski, J Suszycka. Pharmacokinetics of antipyrine in calves after intravenous and oral administration.
Journal of veterinary pharmacology and therapeutics.
1996 Oct; 19(5):408-10. doi:
10.1111/j.1365-2885.1996.tb00073.x. [PMID: 8905578] - K Janus, J Suszycka. Effect of age on the pharmacokinetics of antipyrine in calves.
Research in veterinary science.
1996 May; 60(3):234-7. doi:
10.1016/s0034-5288(96)90045-4. [PMID: 8735513] - H A Ali, A el-Yazigi, J O Sieck, M A Ali, D A Raines, J Saour, P Ernst, B Khan, M Døssing. Antipyrine clearance and metabolite excretion in patients with chronic hepatitis C.
Journal of hepatology.
1995 Jan; 22(1):17-21. doi:
10.1016/0168-8278(95)80254-1. [PMID: 7751582] - H A Ali, A el-Yazigi, J O Sieck, M Døssing, J Saour, D A Raines, P Ernst. Elimination studies of antipyrine and its metabolites in healthy Saudi Arabians.
Human & experimental toxicology.
1994 Oct; 13(10):658-62. doi:
10.1177/096032719401301002. [PMID: 7826682] - R F Witkamp, S M Nijmeijer, H J Kolker, J Noordhoek, A S van Miert. Effect of gonadal hormones on the plasma clearance and metabolite formation of antipyrine in the dwarf goat.
Journal of veterinary pharmacology and therapeutics.
1993 Jun; 16(2):164-73. doi:
10.1111/j.1365-2885.1993.tb00160.x. [PMID: 8345566] - G M Robertz-Vaupel, K D Lindecken, T Edeki, C Funke, S Belwon, H J Dengler. Disposition of antipyrine in patients with extensive metastatic liver disease.
European journal of clinical pharmacology.
1992; 42(5):465-9. doi:
10.1007/bf00314851. [PMID: 1606991] - J V St Peter, Y Abul-Hajj, W M Awni. The pharmacokinetics of antipyrine and three of its metabolites in the rabbit: intravenous administration of pure metabolites.
Pharmaceutical research.
1991 Dec; 8(12):1470-6. doi:
10.1023/a:1015830013451. [PMID: 1808608] - R F Witkamp, J A Lohuis, S M Nijmeijer, H J Kolker, J Noordhoek, A S van Miert. Species- and sex-related differences in the plasma clearance and metabolite formation of antipyrine. A comparative study in four animal species: cattle, goat, rat and rabbit.
Xenobiotica; the fate of foreign compounds in biological systems.
1991 Nov; 21(11):1483-92. doi:
10.3109/00498259109044398. [PMID: 1763522] - N M Waite, M J Rybak, D J Krakovsky, J D Steinberg, L H Warbasse, D J Edwards. Influence of subject age on the inhibition of oxidative metabolism by ciprofloxacin.
Antimicrobial agents and chemotherapy.
1991 Jan; 35(1):130-4. doi:
10.1128/aac.35.1.130. [PMID: 2014968] - R P Shrewsbury, L G White. Evaluation of cytochrome P-450 mediated metabolism of antipyrine in the rat at different extents of fluosol-DA hemodilution.
Research communications in chemical pathology and pharmacology.
1990 Mar; 67(3):411-4. doi:
. [PMID: 2343186] - L B Zavodnik, V M Tsyrkunov, M I Bushma, P I Lukienko, L F Legon'kova. [The effect of diethylnicotinamide (cordiamine) on the activity of the hydroxylating and glucuronyl-conjugating systems in humans].
Farmakologiia i toksikologiia.
1990 Mar; 53(2):50-2. doi:
NULL. [PMID: 2115011] - J V St Peter, W M Awni. Modified high-performance liquid chromatographic assay for antipyrine and its three major metabolites in urine.
Journal of chromatography.
1989 Sep; 494(?):424-7. doi:
10.1016/s0378-4347(00)82699-7. [PMID: 2584343] - R P Shrewsbury, L G White. The effect of moderate fluosol-DA hemodilution on gender specific metabolism of antipyrine.
Research communications in chemical pathology and pharmacology.
1989 Jun; 64(3):455-62. doi:
NULL. [PMID: 2781142] - E Brendel, I Meineke, C de Mey. Assay of antipyrine and its main metabolites 3-hydroxymethylantipyrine, norantipyrine and 4-hydroxyantipyrine in urine.
Journal of pharmaceutical and biomedical analysis.
1989; 7(12):1783-90. doi:
10.1016/0731-7085(89)80194-3. [PMID: 2490567] - M A Mikati, G K Szabo, R J Pylilo, B W LeDuc, T R Browne, D J Greenblatt. Improved high-performance liquid chromatographic assay of antipyrine, hydroxymethylantipyrine, 4-hydroxyantipyrine and norantipyrine in urine.
Journal of chromatography.
1988 Dec; 433(?):305-11. doi:
10.1016/s0378-4347(00)80613-1. [PMID: 3235560] - R P Shrewsbury, L G White. Some insights into the variations in antipyrine pharmacokinetics in the rat.
Research communications in chemical pathology and pharmacology.
1988 Oct; 62(1):137-40. doi:
NULL. [PMID: 3205975] - S Noda, S Kawata, N Ito, S Miyoshi, Y Imai, R Saitoh, S Tamura, M Inada, Y Inui, Y Matsuda. [Alterations of urinary excretion of antipyrine metabolites in patients with cirrhosis of the liver].
Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology.
1987 Nov; 84(11):2531-6. doi:
NULL. [PMID: 2831414] - K Kubota, T Ishizaki, K Chiba, A Takagi, A Nakagawa, K Nakamura. Antipyrine clearance and metabolism in patients with psoriasis.
British journal of clinical pharmacology.
1986 Oct; 22(4):455-62. doi:
10.1111/j.1365-2125.1986.tb02917.x. [PMID: 3768257] - P N Shaw, J B Houston. Temporal effects on antipyrine metabolite kinetics in Aroclor 1254-treated rats.
Toxicology and applied pharmacology.
1986 Jun; 84(2):232-40. doi:
10.1016/0041-008x(86)90130-4. [PMID: 3087023] - D Bach, R Blevins, N Kerner, M Rubenfire, D J Edwards. The effect of verapamil on antipyrine pharmacokinetics and metabolism in man.
British journal of clinical pharmacology.
1986 Jun; 21(6):655-9. doi:
10.1111/j.1365-2125.1986.tb05230.x. [PMID: 3741715] - P N Shaw, J Tseti, S Warburton, A Adedoyin, J B Houston. Inhibition of antipyrine metabolite formation. Steady state studies with cimetidine and metyrapone in rats.
Drug metabolism and disposition: the biological fate of chemicals.
1986 Mar; 14(2):271-6. doi:
. [PMID: 2870906] - J H Rivière, D J Back, A M Breckenridge, R E Howells. The pharmacokinetics of mefloquine in man: lack of effect of mefloquine on antipyrine metabolism.
British journal of clinical pharmacology.
1985 Nov; 20(5):469-74. doi:
10.1111/j.1365-2125.1985.tb05099.x. [PMID: 3878153] - M W Teunissen, L G De Leede, J K Boeijinga, D D Breimer. Correlation between antipyrine metabolite formation and theophylline metabolism in humans after simultaneous single-dose administration and at steady state.
The Journal of pharmacology and experimental therapeutics.
1985 Jun; 233(3):770-5. doi:
. [PMID: 4009489] - M W Teunissen, D Kampf, I Roots, N P Vermeulen, D D Breimer. Antipyrine metabolite formation and excretion in patients with chronic renal failure.
European journal of clinical pharmacology.
1985; 28(5):589-95. doi:
10.1007/bf00544072. [PMID: 4043202] - M W Teunissen, P Spoelstra, C W Koch, B Weeda, W van Duyn, A R Janssens, D D Breimer. Antipyrine clearance and metabolite formation in patients with alcoholic cirrhosis.
British journal of clinical pharmacology.
1984 Nov; 18(5):707-15. doi:
10.1111/j.1365-2125.1984.tb02533.x. [PMID: 6508980] - R M Nash, L Stein, M B Penno, G T Passananti, E S Vesell. Sources of interindividual variations in acetaminophen and antipyrine metabolism.
Clinical pharmacology and therapeutics.
1984 Oct; 36(4):417-30. doi:
10.1038/clpt.1984.199. [PMID: 6541104] - L B Slusher, E S Vesell. Cimetidine-induced reduction in gastrointestinal absorption of antipyrine and rate constants for formation of its metabolites.
Clinical pharmacology and therapeutics.
1984 May; 35(5):568-75. doi:
10.1038/clpt.1984.79. [PMID: 6713770] - M W Teunissen, A Wahlén, E Vinnars, D D Breimer. Influence of alaproclate on antipyrine metabolite formation in man.
European journal of clinical pharmacology.
1984; 27(4):447-52. doi:
10.1007/bf00549593. [PMID: 6519152] - M B Penno, E S Vesell. Monogenic control of variations in antipyrine metabolite formation. New polymorphism of hepatic drug oxidation.
The Journal of clinical investigation.
1983 Jun; 71(6):1698-709. doi:
10.1172/jci110924. [PMID: 6863539] - M W Teunissen, R P Joeres, N P Vermeulen, D D Breimer. Influence of 9-hydroxyellipticine and 3-methylcholanthrene treatment on antipyrine metabolite formation in rats in vivo.
Xenobiotica; the fate of foreign compounds in biological systems.
1983 Apr; 13(4):223-31. doi:
10.3109/00498258309052258. [PMID: 6624137] - B K Tang, H Uchino, T Inaba, W Kalow. Simultaneous determination of antipyrine, 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and norantipyrine in urine by gas chromatography chemical ionization mass spectrometry.
Biomedical mass spectrometry.
1982 Oct; 9(10):425-8. doi:
10.1002/bms.1200091004. [PMID: 7171741] - A Nakagawa, K Nakamura, T Ishizaki, K Chiba. Automated high-performance liqiud chromatographic method for the determination of antipyrine and its metabolites in urine. Some preliminary results obtained from smokers and non-smokers.
Journal of chromatography.
1982 Sep; 231(2):349-60. doi:
10.1016/s0378-4347(00)81860-5. [PMID: 7130315] - J Böttcher, H Bässmann, R Schüppel. Quantitation and urinary pattern of 4,4'-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydroxymethyl-antipyrine, as main metabolites of antipyrine in man and rat.
The Journal of pharmacy and pharmacology.
1982 Mar; 34(3):168-75. doi:
10.1111/j.2042-7158.1982.tb04215.x. [PMID: 6121894] - M Danhof, M W Teunissen, D D Breimer. 3-Hydroxymethyl antipyrine excretion in urine after an oral dose of antipyrine. A reconsideration of previously published data and synthesis of a pure reference substance.
Pharmacology.
1982; 24(3):181-4. doi:
10.1159/000137594. [PMID: 7071130]
