(R)-Warfarin (BioDeep_00000855634)
代谢物信息卡片
(S)-(−)-Warfarin
化学式: C19H16O4 (308.1049)
中文名称: R-文拉法辛
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O
InChI: InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m1/s1
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:87737
- PubChem: 54684598
- DrugBank: DB08496
- ChEMBL: CHEMBL251073
- CAS: 5543-58-8
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)
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。
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 |
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文献列表
- Berit Packert Jensen, Paul Ken Leong Chin, Rebecca Lee Roberts, Evan James Begg. Influence of adult age on the total and free clearance and protein binding of (R)- and (S)-warfarin.
British journal of clinical pharmacology.
2012 Nov; 74(5):797-805. doi:
10.1111/j.1365-2125.2012.04259.x. [PMID: 22380743] - Martha Gonzalez, Peter Zannikos, Allitia DiBernardo, H Robert Brashear, Jay Ariyawansa. Effect of carisbamate on the pharmacokinetics and pharmacodynamics of warfarin in healthy participants.
Journal of clinical pharmacology.
2012 Sep; 52(9):1420-9. doi:
10.1177/0091270011415412. [PMID: 22011511] - K Nakamura, K Obayashi, T Araki, T Aomori, Y Fujita, Y Okada, M Kurabayashi, A Hasegawa, S Ohmori, T Nakamura, K Yamamoto. CYP4F2 gene polymorphism as a contributor to warfarin maintenance dose in Japanese subjects.
Journal of clinical pharmacy and therapeutics.
2012 Aug; 37(4):481-5. doi:
10.1111/j.1365-2710.2011.01317.x. [PMID: 22172097] - Namyi Gu, Bo-Hyung Kim, Kyoung Soo Lim, Sung Eun Kim, Won Seok Nam, Seo Hyun Yoon, Joo-Youn Cho, Sang-Goo Shin, In-Jin Jang, Kyung-Sang Yu. The effect of fimasartan, an angiotensin receptor type 1 blocker, on the pharmacokinetics and pharmacodynamics of warfarin in healthy Korean male volunteers: a one-sequence, two-period crossover clinical trial.
Clinical therapeutics.
2012 Jul; 34(7):1592-600. doi:
10.1016/j.clinthera.2012.06.004. [PMID: 22727611] - Kyung-Eun Lee, Byung-Chul Chang, Han-Oll Kim, In-Kyung Yoon, Na-Ra Lee, Hee-Yoon Park, Hye-Sun Gwak. Effects of CYP4F2 gene polymorphisms on warfarin clearance and sensitivity in Korean patients with mechanical cardiac valves.
Therapeutic drug monitoring.
2012 Jun; 34(3):275-82. doi:
10.1097/ftd.0b013e318256a77c. [PMID: 22549502] - Arnaud Tonnelier, Sandra Coecke, José-Manuel Zaldívar. Screening of chemicals for human bioaccumulative potential with a physiologically based toxicokinetic model.
Archives of toxicology.
2012 Mar; 86(3):393-403. doi:
10.1007/s00204-011-0768-0. [PMID: 22089525] - Yuko Taki, Kaori Yokotani, Shizuo Yamada, Kazumasa Shinozuka, Yoko Kubota, Yasuo Watanabe, Keizo Umegaki. Ginkgo biloba extract attenuates warfarin-mediated anticoagulation through induction of hepatic cytochrome P450 enzymes by bilobalide in mice.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Jan; 19(2):177-82. doi:
10.1016/j.phymed.2011.06.020. [PMID: 21802929] - Steven Lane, Sameh Al-Zubiedi, Ellen Hatch, Ivan Matthews, Andrea L Jorgensen, Panos Deloukas, Ann K Daly, B Kevin Park, Leon Aarons, Kayode Ogungbenro, Farhad Kamali, Dyfrig Hughes, Munir Pirmohamed. The population pharmacokinetics of R- and S-warfarin: effect of genetic and clinical factors.
British journal of clinical pharmacology.
2012 Jan; 73(1):66-76. doi:
10.1111/j.1365-2125.2011.04051.x. [PMID: 21692828] - Shu Jin, Yi-Fan Zhang, Xiao-Yan Chen, Ke Liu, Da-Fang Zhong. [Enantioselective determinination of R-warfarin/S-warfarin in human plasma using liquid chromatography-tandem mass spectrometry and its application in a drug-drug interaction study].
Yao xue xue bao = Acta pharmaceutica Sinica.
2012 Jan; 47(1):105-9. doi:
NULL. [PMID: 22493814] - Masatomo Miura, Naoto Takahashi, Syu-ichi Kanno, Shoutaro Kato, Miho Nara, Mitsugu Itoh, Hirobumi Saitoh, Tomoko Yoshioka, Yoshihiro Kameoka, Naohito Fujishima, Hiroyuki Tagawa, Makoto Hirokawa, Kenichi Sawada. Drug interaction of (S)-warfarin, and not (R)-warfarin, with itraconazole in a hematopoietic stem cell transplant recipient.
Clinica chimica acta; international journal of clinical chemistry.
2011 Oct; 412(21-22):2002-6. doi:
10.1016/j.cca.2011.06.035. [PMID: 21771587] - Bimal Malhotra, Christine Alvey, Jason Gong, Xiaoxi Li, Gregory Duczynski, Kuan Gandelman. Effects of fesoterodine on the pharmacokinetics and pharmacodynamics of warfarin in healthy volunteers.
British journal of clinical pharmacology.
2011 Aug; 72(2):257-62. doi:
10.1111/j.1365-2125.2011.03989.x. [PMID: 21496065] - N McCracken, G Lahu, T D Bethke. Lack of pharmacokinetic and pharmacodynamic interactions of roflumilast with (R, S)-warfarin in healthy adult subjects.
International journal of clinical pharmacology and therapeutics.
2011 Jun; 49(6):388-96. doi:
10.5414/cp201523. [PMID: 21612746] - Drew R Jones, Gunnar Boysen, Grover P Miller. Novel multi-mode ultra performance liquid chromatography-tandem mass spectrometry assay for profiling enantiomeric hydroxywarfarins and warfarin in human plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 May; 879(15-16):1056-62. doi:
10.1016/j.jchromb.2011.03.022. [PMID: 21470921] - Masatomo Miura, Shin Okuyama, Shoutaro Kato, Hideaki Kagaya, Atsunobu Murata, Atsushi Komatsuda, Hideki Wakui, Kenichi Sawada. Simultaneous determination of warfarin and 7-hydroxywarfarin enantiomers by high-performance liquid chromatography with ultraviolet detection.
Therapeutic drug monitoring.
2011 Feb; 33(1):108-14. doi:
10.1097/ftd.0b013e31820176d6. [PMID: 21157402] - Ophelia Q P Yin, Neil Gallagher, Deirdre Fischer, Lily Zhao, Wei Zhou, Elisabeth Leroy, Georg Golor, Horst Schran. Effects of nilotinib on single-dose warfarin pharmacokinetics and pharmacodynamics: a randomized, single-blind, two-period crossover study in healthy subjects.
Clinical drug investigation.
2011; 31(3):169-79. doi:
10.2165/11538700-000000000-00000. [PMID: 21184622] - Ramasamy Saminathan, Jing Bai, Laleh Sadrolodabaee, Govindasamy Muralidharan Karthik, Onkar Singh, Koilan Subramaniyan, Chi Bun Ching, Wei Ning Chen, Balram Chowbay. VKORC1 pharmacogenetics and pharmacoproteomics in patients on warfarin anticoagulant therapy: transthyretin precursor as a potential biomarker.
PloS one.
2010 Dec; 5(12):e15064. doi:
10.1371/journal.pone.0015064. [PMID: 21179214] - Richard Kones. Rosuvastatin, inflammation, C-reactive protein, JUPITER, and primary prevention of cardiovascular disease--a perspective.
Drug design, development and therapy.
2010 Dec; 4(?):383-413. doi:
10.2147/dddt.s10812. [PMID: 21267417] - Markus Rauchenzauner, Gerhard Luef. Update on treatment of partial onset epilepsy: role of eslicarbazepine.
Neuropsychiatric disease and treatment.
2010 Nov; 6(?):723-30. doi:
10.2147/ndt.s5840. [PMID: 21127691] - A Frymoyer, S Shugarts, M Browne, A H B Wu, L Frassetto, L Z Benet. Effect of single-dose rifampin on the pharmacokinetics of warfarin in healthy volunteers.
Clinical pharmacology and therapeutics.
2010 Oct; 88(4):540-7. doi:
10.1038/clpt.2010.142. [PMID: 20703222] - Toshiharu Goto, Masatomo Miura, Atsunobu Murata, Ken Terata, Tsukasa Uno, Koujirou Yamamoto, Yoshihisa Abe. Standard warfarin dose in a patient with the CYP2C9*3/*3 genotype leads to hematuria.
Clinica chimica acta; international journal of clinical chemistry.
2010 Sep; 411(17-18):1375-7. doi:
10.1016/j.cca.2010.04.014. [PMID: 20420818] - Qun Su, Yuhong Li. Interaction between warfarin and the herbal product Shengmai-yin: a case report of intracerebral hematoma.
Yonsei medical journal.
2010 Sep; 51(5):793-6. doi:
10.3349/ymj.2010.51.5.793. [PMID: 20635460] - Zhong Zuo, Siu Kwan Wo, Cindy M Y Lo, Limin Zhou, Gregory Cheng, Joyce H S You. Simultaneous measurement of S-warfarin, R-warfarin, S-7-hydroxywarfarin and R-7-hydroxywarfarin in human plasma by liquid chromatography-tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2010 Jun; 52(2):305-10. doi:
10.1016/j.jpba.2010.01.005. [PMID: 20133101] - Drew R Jones, So-Young Kim, Michael Guderyon, Chul-Ho Yun, Jeffery H Moran, Grover P Miller. Hydroxywarfarin metabolites potently inhibit CYP2C9 metabolism of S-warfarin.
Chemical research in toxicology.
2010 May; 23(5):939-45. doi:
10.1021/tx1000283. [PMID: 20429590] - Gisela I Robles, Devada Singh-Franco. A review of exenatide as adjunctive therapy in patients with type 2 diabetes.
Drug design, development and therapy.
2009 Sep; 3(?):219-40. doi:
10.2147/dddt.s3321. [PMID: 19920937] - Michelle J Yoo, David S Hage. Evaluation of silica monoliths in affinity microcolumns for high-throughput analysis of drug-protein interactions.
Journal of separation science.
2009 Aug; 32(15-16):2776-85. doi:
10.1002/jssc.200900346. [PMID: 19630007] - Jack Ansell, Maryellen McDonough, Yanli Zhao, Jerold S Harmatz, David J Greenblatt. The absence of an interaction between warfarin and cranberry juice: a randomized, double-blind trial.
Journal of clinical pharmacology.
2009 Jul; 49(7):824-30. doi:
10.1177/0091270009337510. [PMID: 19553405] - Gennyne Walker, Arun Mandagere, Christopher Dufton, Jürgen Venitz. The pharmacokinetics and pharmacodynamics of warfarin in combination with ambrisentan in healthy volunteers.
British journal of clinical pharmacology.
2009 May; 67(5):527-34. doi:
10.1111/j.1365-2125.2009.03384.x. [PMID: 19552747] - Eli Chan, Akhil Hegde, Xin Chen. Effect of rutin on warfarin anticoagulation and pharmacokinetics of warfarin enantiomers in rats.
The Journal of pharmacy and pharmacology.
2009 Apr; 61(4):451-8. doi:
10.1211/jpp/61.04.0006. [PMID: 19298691] - M I Mohammed Abdul, X Jiang, K M Williams, R O Day, B D Roufogalis, W S Liauw, H Xu, A J McLachlan. Pharmacodynamic interaction of warfarin with cranberry but not with garlic in healthy subjects.
British journal of pharmacology.
2008 Aug; 154(8):1691-700. doi:
10.1038/bjp.2008.210. [PMID: 18516070] - Tsukasa Uno, Katsuyoshi Sugimoto, Kazunobu Sugawara, Tomonori Tateishi. The role of cytochrome P2C19 in R-warfarin pharmacokinetics and its interaction with omeprazole.
Therapeutic drug monitoring.
2008 Jun; 30(3):276-81. doi:
10.1097/ftd.0b013e31816e2d8e. [PMID: 18520598] - Rangan Mallik, David S Hage. Development of an affinity silica monolith containing human serum albumin for chiral separations.
Journal of pharmaceutical and biomedical analysis.
2008 Apr; 46(5):820-30. doi:
10.1016/j.jpba.2007.03.017. [PMID: 17475436] - T Uno, K Sugimoto, K Sugawara, T Tateishi. The effect of CYP2C19 genotypes on the pharmacokinetics of warfarin enantiomers.
Journal of clinical pharmacy and therapeutics.
2008 Feb; 33(1):67-73. doi:
10.1111/j.1365-2710.2008.00887.x. [PMID: 18211619] - Srinivasan Shanmugam, Eung Seok Lee, Tae Cheon Jeong, Chul Soon Yong, Han-Gon Choi, Jong-Soo Woo, Bong Kyu Yoo. The effect of 1-furan-2-yl-3-pyridine-2-yl-propenone on pharmacokinetic parameters of warfarin.
Archives of pharmacal research.
2007 Jul; 30(7):898-904. doi:
10.1007/bf02978843. [PMID: 17703744] - Tsukasa Uno, Takenori Niioka, Makoto Hayakari, Kazunobu Sugawara, Tomonori Tateishi. Simultaneous determination of warfarin enantiomers and its metabolite in human plasma by column-switching high-performance liquid chromatography with chiral separation.
Therapeutic drug monitoring.
2007 Jun; 29(3):333-9. doi:
10.1097/ftd.0b013e31805c956e. [PMID: 17529891] - J J Lilja, J T Backman, P J Neuvonen. Effects of daily ingestion of cranberry juice on the pharmacokinetics of warfarin, tizanidine, and midazolam--probes of CYP2C9, CYP1A2, and CYP3A4.
Clinical pharmacology and therapeutics.
2007 Jun; 81(6):833-9. doi:
10.1038/sj.clpt.6100149. [PMID: 17392729] - Abdimajid Osman, Camilla Enström, Tomas L Lindahl. Plasma S/R ratio of warfarin co-varies with VKORC1 haplotype.
Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis.
2007 Apr; 18(3):293-6. doi:
10.1097/mbc.0b013e3280444bfd. [PMID: 17413769] - Mordechai Muszkat, Simcha Blotnik, Amir Elami, Irena Krasilnikov, Yoseph Caraco. Warfarin metabolism and anticoagulant effect: a prospective, observational study of the impact of CYP2C9 genetic polymorphism in the presence of drug-disease and drug-drug interactions.
Clinical therapeutics.
2007 Mar; 29(3):427-37. doi:
10.1016/s0149-2918(07)80081-6. [PMID: 17577464] - Roger A Coe, Jonathan O Rathe, Jean W Lee. Supercritical fluid chromatography-tandem mass spectrometry for fast bioanalysis of R/S-warfarin in human plasma.
Journal of pharmaceutical and biomedical analysis.
2006 Nov; 42(5):573-80. doi:
10.1016/j.jpba.2006.05.025. [PMID: 16875793] - Kyoko Obayashi, Katsunori Nakamura, Junichi Kawana, Hiroyasu Ogata, Kazuhiko Hanada, Masahiko Kurabayashi, Akira Hasegawa, Koujirou Yamamoto, Ryuya Horiuchi. VKORC1 gene variations are the major contributors of variation in warfarin dose in Japanese patients.
Clinical pharmacology and therapeutics.
2006 Aug; 80(2):169-78. doi:
10.1016/j.clpt.2006.04.010. [PMID: 16890578] - A Osman, C Enström, K Arbring, P Söderkvist, T L Lindahl. Main haplotypes and mutational analysis of vitamin K epoxide reductase (VKORC1) in a Swedish population: a retrospective analysis of case records.
Journal of thrombosis and haemostasis : JTH.
2006 Aug; 4(8):1723-9. doi:
10.1111/j.1538-7836.2006.02039.x. [PMID: 16879214] - Darja Herman, Igor Locatelli, Iztok Grabnar, Polona Peternel, Mojca Stegnar, Mitja Lainscak, Ales Mrhar, Katja Breskvar, Vita Dolzan. The influence of co-treatment with carbamazepine, amiodarone and statins on warfarin metabolism and maintenance dose.
European journal of clinical pharmacology.
2006 Apr; 62(4):291-6. doi:
10.1007/s00228-006-0104-4. [PMID: 16552506] - Abdimajid Osman, Kerstin Arbring, Tomas L Lindahl. A new high-performance liquid chromatographic method for determination of warfarin enantiomers.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Nov; 826(1-2):75-80. doi:
10.1016/j.jchromb.2005.08.011. [PMID: 16143572] - Elizabeth A Sconce, Tayyaba I Khan, Hilary A Wynne, Peter Avery, Louise Monkhouse, Barry P King, Peter Wood, Patrick Kesteven, Ann K Daly, Farhad Kamali. The impact of CYP2C9 and VKORC1 genetic polymorphism and patient characteristics upon warfarin dose requirements: proposal for a new dosing regimen.
Blood.
2005 Oct; 106(7):2329-33. doi:
10.1182/blood-2005-03-1108. [PMID: 15947090] - Ross Camidge, Bruno Reigner, Jim Cassidy, Susan Grange, Markus Abt, Erhard Weidekamm, Duncan Jodrell. Significant effect of capecitabine on the pharmacokinetics and pharmacodynamics of warfarin in patients with cancer.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2005 Jul; 23(21):4719-25. doi:
10.1200/jco.2005.09.129. [PMID: 16034047] - Xuemin Jiang, Kenneth M Williams, Winston S Liauw, Alaina J Ammit, Basil D Roufogalis, Colin C Duke, Richard O Day, Andrew J McLachlan. Effect of ginkgo and ginger on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects.
British journal of clinical pharmacology.
2005 Apr; 59(4):425-32. doi:
10.1111/j.1365-2125.2005.02322.x. [PMID: 15801937] - Jari J Lilja, Janne T Backman, Pertti J Neuvonen. Effect of gemfibrozil on the pharmacokinetics and pharmacodynamics of racemic warfarin in healthy subjects.
British journal of clinical pharmacology.
2005 Apr; 59(4):433-9. doi:
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Analytical chemistry.
2004 Dec; 76(23):7013-22. doi:
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2004 Sep; 1049(1-2):51-61. doi:
10.1016/s0021-9673(04)01338-x. [PMID: 15499917] - Xuemin Jiang, Kenneth M Williams, Winston S Liauw, Alaina J Ammit, Basil D Roufogalis, Colin C Duke, Richard O Day, Andrew J McLachlan. Effect of St John's wort and ginseng on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects.
British journal of clinical pharmacology.
2004 May; 57(5):592-9. doi:
10.1111/j.1365-2125.2003.02051.x. [PMID: 15089812] - Farhad Kamali, Tayyaba Irfan Khan, Barry P King, Richard Frearson, Patrick Kesteven, Peter Wood, Ann K Daly, Hilary Wynne. Contribution of age, body size, and CYP2C9 genotype to anticoagulant response to warfarin.
Clinical pharmacology and therapeutics.
2004 Mar; 75(3):204-12. doi:
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Analytical chemistry.
2003 Nov; 75(22):6295-305. doi:
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2003 Aug; 31(8):1043-8. doi:
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Journal of biochemical and biophysical methods.
2002 Dec; 54(1-3):315-26. doi:
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2002 Dec; 72(6):702-10. doi:
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Journal of thrombosis and thrombolysis.
2002 Dec; 14(3):227-32. doi:
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Chirality.
2002 May; 14(5):442-8. doi:
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2001 Jul; 41(7):715-22. doi:
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The Journal of biological chemistry.
2001 Jun; 276(25):22804-9. doi:
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2001 Apr; 41(4):459-64. doi:
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Clinical pharmacokinetics.
2001; 40(7):523-37. doi:
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Drug metabolism and drug interactions.
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