Simvastatin acid (BioDeep_00000572829)
Main id: BioDeep_00000014131
代谢物信息卡片
Simvastatin acid
化学式: C25H40O6 (436.28247400000004)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)C
InChI: InChI=1S/C25H40O6/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29)/t15-,16-,18+,19+,20-,21-,23-/m0/s1
描述信息
C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent
C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor
同义名列表
1 个代谢物同义名
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:169041
- KEGG: C21581
- PubChem: 64718
- Metlin: METLIN2447
- DrugBank: DB14714
- ChEMBL: CHEMBL1201391
- CAS: 121009-77-6
- PubChem: 340125642
- PDB-CCD: SIM
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。
文献列表
- Meili Shen, Hui Jiang, Yan Zhao, Liangqiang Wu, Haiqin Yang, Yixuan Yao, Hao Meng, Qingbiao Yang, Linlin Liu, Yapeng Li. Shear Stress and ROS Dual-Responsive RBC-Hitchhiking Nanoparticles for Atherosclerosis Therapy.
ACS applied materials & interfaces.
2023 Sep; 15(37):43374-43386. doi:
10.1021/acsami.3c07371. [PMID: 37669139] - Yu Zhang, Jian He, Xiao Tang, Zunjian Zhang, Yuan Tian. A validated LC-MS/MS method for simultaneous quantification of simvastatin and simvastatin acid in beagle plasma: Application to an absolute bioavailability study.
Biomedical chromatography : BMC.
2022 Mar; 36(3):e5290. doi:
10.1002/bmc.5290. [PMID: 34854096] - Ziwei Li, Jun Zhang, Yufeng Zhang, Zhong Zuo. Role of esterase mediated hydrolysis of simvastatin in human and rat blood and its impact on pharmacokinetic profiles of simvastatin and its active metabolite in rat.
Journal of pharmaceutical and biomedical analysis.
2019 May; 168(?):13-22. doi:
10.1016/j.jpba.2019.02.004. [PMID: 30776567] - Asma El-Zailik, Lily K Cheung, Yang Wang, Vadim Sherman, Diana S-L Chow. Simultaneous LC-MS/MS analysis of simvastatin, atorvastatin, rosuvastatin and their active metabolites for plasma samples of obese patients underwent gastric bypass surgery.
Journal of pharmaceutical and biomedical analysis.
2019 Feb; 164(?):258-267. doi:
10.1016/j.jpba.2018.10.045. [PMID: 30396053] - Robert Elsby, Victoria Hare, Hannah Neal, Samuel Outteridge, Catherine Pearson, Katie Plant, Rachel Upcott Gill, Philip Butler, Robert J Riley. Mechanistic In Vitro Studies Indicate that the Clinical Drug-Drug Interaction between Telithromycin and Simvastatin Acid Is Driven by Time-Dependent Inhibition of CYP3A4 with Minimal Effect on OATP1B1.
Drug metabolism and disposition: the biological fate of chemicals.
2019 01; 47(1):1-8. doi:
10.1124/dmd.118.083832. [PMID: 30348903] - Jung-Ryul Kim, Jin Ah Jung, Seokuee Kim, Wooseong Huh, Jong-Lyul Ghim, Jae-Gook Shin, Jae-Wook Ko. Effect of Cilostazol on the Pharmacokinetics of Simvastatin in Healthy Subjects.
BioMed research international.
2019; 2019(?):1365180. doi:
10.1155/2019/1365180. [PMID: 30729119] - Wei Yang, Qiuyang Zhang, Yue Yang, Jiaqiu Xu, Ali Fan, Chung S Yang, Ning Li, Yang Lu, Jiayin Chen, Di Zhao, Jiye Aa, Xijing Chen. Epigallocatechin-3-gallate decreases the transport and metabolism of simvastatin in rats.
Xenobiotica; the fate of foreign compounds in biological systems.
2017 Jan; 47(1):86-92. doi:
10.3109/00498254.2016.1159747. [PMID: 27052517] - Pankaj Partani, Saurabh Manaswita Verma, Tausif Monif. Development and Validation of an LC-MS-MS Method for Determination of Simvastatin and Simvastatin Acid in Human Plasma: Application to a Pharmacokinetic Study.
Journal of chromatographic science.
2016 Sep; 54(8):1385-96. doi:
10.1093/chromsci/bmw087. [PMID: 27226460] - Dhiaa A Taha, Cornelia H De Moor, David A Barrett, Jong Bong Lee, Raj D Gandhi, Chee Wei Hoo, Pavel Gershkovich. The role of acid-base imbalance in statin-induced myotoxicity.
Translational research : the journal of laboratory and clinical medicine.
2016 08; 174(?):140-160.e14. doi:
10.1016/j.trsl.2016.03.015. [PMID: 27083388] - Sathish Babu Munaga, Rajani Kumar Valluru, Phani Bhushana Reddy Bonga, V Sumathi Rao, Hemanth Kumar Sharma. Development and Validation of an LC-MS-MS Method for the Simultaneous Determination of Simvastatin, Simvastatin Acid and Ezetimibe in Human Plasma and Its Application to Pharmacokinetic Study in the Indian Population.
Journal of chromatographic science.
2016 Jul; 54(6):985-96. doi:
10.1093/chromsci/bmw043. [PMID: 27048644] - Andrew Marsh, Katherine Casey-Green, Fay Probert, David Withall, Daniel A Mitchell, Suzanne J Dilly, Sean James, Wade Dimitri, Sweta R Ladwa, Paul C Taylor, Donald R J Singer. Simvastatin Sodium Salt and Fluvastatin Interact with Human Gap Junction Gamma-3 Protein.
PloS one.
2016; 11(2):e0148266. doi:
10.1371/journal.pone.0148266. [PMID: 26863535] - Hee Youn Choi, Kyun-Seop Bae, Sang-Heon Cho, Jong-Lyul Ghim, Sangmin Choe, Jin Ah Jung, Seok-Joon Jin, Hee-Sun Kim, Hyeong-Seok Lim. Impact of CYP2D6, CYP3A5, CYP2C19, CYP2A6, SLCO1B1, ABCB1, and ABCG2 gene polymorphisms on the pharmacokinetics of simvastatin and simvastatin acid.
Pharmacogenetics and genomics.
2015 Dec; 25(12):595-608. doi:
10.1097/fpc.0000000000000176. [PMID: 26367500] - Jasmine A Luzum, Elizabeth Theusch, Kent D Taylor, Ann Wang, Wolfgang Sadee, Philip F Binkley, Ronald M Krauss, Marisa W Medina, Joseph P Kitzmiller. Individual and Combined Associations of Genetic Variants in CYP3A4, CYP3A5, and SLCO1B1 With Simvastatin and Simvastatin Acid Plasma Concentrations.
Journal of cardiovascular pharmacology.
2015 Jul; 66(1):80-5. doi:
10.1097/fjc.0000000000000246. [PMID: 26164721] - Nikolaos Tsamandouras, Gemma Dickinson, Yingying Guo, Stephen Hall, Amin Rostami-Hodjegan, Aleksandra Galetin, Leon Aarons. Development and Application of a Mechanistic Pharmacokinetic Model for Simvastatin and its Active Metabolite Simvastatin Acid Using an Integrated Population PBPK Approach.
Pharmaceutical research.
2015 Jun; 32(6):1864-83. doi:
10.1007/s11095-014-1581-2. [PMID: 25446771] - Abdulrahman K Al-Asmari, Zabih Ullah, Fahad Al-Sabaan, Mohammad Tariq, Ahmed Al-Eid, Saud F Al-Omani. Effect of vitamin D on bioavailability and lipid lowering efficacy of simvastatin.
European journal of drug metabolism and pharmacokinetics.
2015 Mar; 40(1):87-94. doi:
10.1007/s13318-014-0183-z. [PMID: 24740652] - Bruce K Birmingham, Sarah R Bujac, Robert Elsby, Connie T Azumaya, Cheryl Wei, Yusong Chen, Rogelio Mosqueda-Garcia, Helen J Ambrose. Impact of ABCG2 and SLCO1B1 polymorphisms on pharmacokinetics of rosuvastatin, atorvastatin and simvastatin acid in Caucasian and Asian subjects: a class effect?.
European journal of clinical pharmacology.
2015 Mar; 71(3):341-55. doi:
10.1007/s00228-014-1801-z. [PMID: 25673568] - Jiang Wang, Jasmine A Luzum, Mitch A Phelps, Joseph P Kitzmiller. Liquid chromatography-tandem mass spectrometry assay for the simultaneous quantification of simvastatin, lovastatin, atorvastatin, and their major metabolites in human plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Mar; 983-984(?):18-25. doi:
10.1016/j.jchromb.2014.12.029. [PMID: 25612772] - Martine Gehin, Patricia N Sidharta, Carmela Gnerre, Alexander Treiber, Atef Halabi, Jasper Dingemanse. Pharmacokinetic interactions between simvastatin and setipiprant, a CRTH2 antagonist.
European journal of clinical pharmacology.
2015 Jan; 71(1):15-23. doi:
10.1007/s00228-014-1767-x. [PMID: 25323804] - Qian Zhao, Ji Jiang, Pei Hu. Effects of four traditional Chinese medicines on the pharmacokinetics of simvastatin.
Xenobiotica; the fate of foreign compounds in biological systems.
2015; 45(9):803-10. doi:
10.3109/00498254.2015.1019593. [PMID: 25801058] - Sreeraj Macha, Benjamin Lang, Sabine Pinnetti, Uli C Broedl. Pharmacokinetics of empagliflozin, a sodium glucose cotransporter 2 inhibitor, and simvastatin following co-administration in healthy volunteers.
International journal of clinical pharmacology and therapeutics.
2014 Nov; 52(11):973-80. doi:
10.5414/cp202117. [PMID: 25161155] - Dan Xu, Feng Li, Mian Zhang, Ji Zhang, Can Liu, Meng-yue Hu, Ze-yu Zhong, Ling-ling Jia, Da-wei Wang, Jie Wu, Li Liu, Xiao-dong Liu. Decreased exposure of simvastatin and simvastatin acid in a rat model of type 2 diabetes.
Acta pharmacologica Sinica.
2014 Sep; 35(9):1215-25. doi:
10.1038/aps.2014.39. [PMID: 25152023] - N Tsamandouras, G Dickinson, Y Guo, S Hall, A Rostami-Hodjegan, A Galetin, L Aarons. Identification of the effect of multiple polymorphisms on the pharmacokinetics of simvastatin and simvastatin acid using a population-modeling approach.
Clinical pharmacology and therapeutics.
2014 Jul; 96(1):90-100. doi:
10.1038/clpt.2014.55. [PMID: 24598718] - Seok-Joon Jin, Kyun-Seop Bae, Sang-Heon Cho, Jin-Ah Jung, Unjib Kim, Sangmin Choe, Jong-Lyul Ghim, Yook-Hwan Noh, Hyun-Jung Park, Hee-Sun Kim, Hyeong-Seok Lim. Population pharmacokinetic analysis of simvastatin and its active metabolite with the characterization of atypical complex absorption kinetics.
Pharmaceutical research.
2014 Jul; 31(7):1801-12. doi:
10.1007/s11095-013-1284-0. [PMID: 24549818] - M Liu, X L Wang, D Zhang, M Yang, J Han, Y N Zhang, Z L Wang, H C Liu. Pharmacokinetics of niacin, simvastatin and their metabolites in healthy Chinese subjects after single and multiple doses of a fixed dose combination tablet of niacin extended release/simvastatin.
Drug research.
2014 Jun; 64(6):296-300. doi:
10.1055/s-0033-1357190. [PMID: 24154936] - Ling-Ling Dai, Lan Fan, Hui-Zi Wu, Zhi-Rong Tan, Yao Chen, Xiang-Dong Peng, Min-Xue Shen, Guo-Ping Yang, Hong-Hao Zhou. Assessment of a pharmacokinetic and pharmacodynamic interaction between simvastatin and Ginkgo biloba extracts in healthy subjects.
Xenobiotica; the fate of foreign compounds in biological systems.
2013 Oct; 43(10):862-7. doi:
10.3109/00498254.2013.773385. [PMID: 23451885] - Joseph W Polli, Elizabeth Hussey, Mark Bush, Grant Generaux, Glenn Smith, David Collins, Susan McMullen, Nancy Turner, Derek J Nunez. Evaluation of drug interactions of GSK1292263 (a GPR119 agonist) with statins: from in vitro data to clinical study design.
Xenobiotica; the fate of foreign compounds in biological systems.
2013 Jun; 43(6):498-508. doi:
10.3109/00498254.2012.739719. [PMID: 23256625] - Teddy Kosoglou, Yali Zhu, Paul Statkevich, Ilias Triantafyllou, William Taggart, Fengjuan Xuan, Kenneth T Kim, David L Cutler. Assessment of potential pharmacokinetic interactions of ezetimibe/simvastatin and extended-release niacin tablets in healthy subjects.
European journal of clinical pharmacology.
2011 May; 67(5):483-92. doi:
10.1007/s00228-010-0955-6. [PMID: 21120461] - Zhiwen Zhang, Huihui Bu, Zhiwei Gao, Yan Huang, Fang Gao, Yaping Li. The characteristics and mechanism of simvastatin loaded lipid nanoparticles to increase oral bioavailability in rats.
International journal of pharmaceutics.
2010 Jul; 394(1-2):147-53. doi:
10.1016/j.ijpharm.2010.04.039. [PMID: 20435111] - Jun Zhang, Ramona Rodila, Eric Gage, Mathew Hautman, Leimin Fan, Linda L King, Huaiqin Wu, Tawakol A El-Shourbagy. High-throughput salting-out assisted liquid/liquid extraction with acetonitrile for the simultaneous determination of simvastatin and simvastatin acid in human plasma with liquid chromatography.
Analytica chimica acta.
2010 Feb; 661(2):167-72. doi:
10.1016/j.aca.2009.12.023. [PMID: 20113731] - Addepalli V Ramani, Pinaki Sengupta, Ramesh Mullangi. Development and validation of a highly sensitive and robust LC-ESI-MS/MS method for simultaneous quantitation of simvastatin acid, amlodipine and valsartan in human plasma: application to a clinical pharmacokinetic study.
Biomedical chromatography : BMC.
2009 Jun; 23(6):615-22. doi:
10.1002/bmc.1161. [PMID: 19277959] - Constantinos Apostolou, Constantinos Kousoulos, Yannis Dotsikas, Georgios-Stefanos Soumelas, Filomila Kolocouri, Afroditi Ziaka, Yannis L Loukas. An improved and fully validated LC-MS/MS method for the simultaneous quantification of simvastatin and simvastatin acid in human plasma.
Journal of pharmaceutical and biomedical analysis.
2008 Mar; 46(4):771-9. doi:
10.1016/j.jpba.2007.12.001. [PMID: 18201852] - Surya P Ayalasomayajula, Kiran Dole, Yan-Ling He, Monica Ligueros-Saylan, Yibin Wang, Joelle Campestrini, Henri Humbert, Gangadhar Sunkara. Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects.
Current medical research and opinion.
2007 Dec; 23(12):2913-20. doi:
10.1185/030079907x233296. [PMID: 17931461] - Cuiping Chen, Jian Lin, Teresa Smolarek, Larry Tremaine. P-glycoprotein has differential effects on the disposition of statin acid and lactone forms in mdr1a/b knockout and wild-type mice.
Drug metabolism and disposition: the biological fate of chemicals.
2007 Oct; 35(10):1725-9. doi:
10.1124/dmd.107.015677. [PMID: 17640956] - Marja K Pasanen, Mikko Neuvonen, Pertti J Neuvonen, Mikko Niemi. SLCO1B1 polymorphism markedly affects the pharmacokinetics of simvastatin acid.
Pharmacogenetics and genomics.
2006 Dec; 16(12):873-9. doi:
10.1097/01.fpc.0000230416.82349.90. [PMID: 17108811] - Masaki Kobayashi, Yukio Otsuka, Shirou Itagaki, Takeshi Hirano, Ken Iseki. Inhibitory effects of statins on human monocarboxylate transporter 4.
International journal of pharmaceutics.
2006 Jul; 317(1):19-25. doi:
10.1016/j.ijpharm.2006.02.043. [PMID: 16621368] - Masao Yoshinari, Tohru Hayakawa, Kenichi Matsuzaka, Takashi Inoue, Yutaka Oda, Masaki Shimono, Takaharu Ide, Teruo Tanaka. Oxygen plasma surface modification enhances immobilization of simvastatin acid.
Biomedical research (Tokyo, Japan).
2006 Feb; 27(1):29-36. doi:
10.2220/biomedres.27.29. [PMID: 16543663] - Thomayant Prueksaritanont, Yue Qiu, Lillian Mu, Kimberly Michel, Janice Brunner, Karen M Richards, Jiunn H Lin. Interconversion pharmacokinetics of simvastatin and its hydroxy acid in dogs: effects of gemfibrozil.
Pharmaceutical research.
2005 Jul; 22(7):1101-9. doi:
10.1007/s11095-005-6037-2. [PMID: 16028010] - Cuiping Chen, Rouchelle J Mireles, Scott D Campbell, Jian Lin, Jessica B Mills, Jinghai J Xu, Teresa A Smolarek. Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Apr; 33(4):537-46. doi:
10.1124/dmd.104.002477. [PMID: 15616150] - Jari J Lilja, Mikko Neuvonen, Pertti J Neuvonen. Effects of regular consumption of grapefruit juice on the pharmacokinetics of simvastatin.
British journal of clinical pharmacology.
2004 Jul; 58(1):56-60. doi:
10.1111/j.1365-2125.2004.02095.x. [PMID: 15206993] - M Ucar, M Neuvonen, H Luurila, R Dahlqvist, P J Neuvonen, T Mjörndal. Carbamazepine markedly reduces serum concentrations of simvastatin and simvastatin acid.
European journal of clinical pharmacology.
2004 Feb; 59(12):879-82. doi:
10.1007/s00228-003-0700-5. [PMID: 14691614] - Nanyan Zhang, Amy Yang, John Douglas Rogers, Jamie J Zhao. Quantitative analysis of simvastatin and its beta-hydroxy acid in human plasma using automated liquid-liquid extraction based on 96-well plate format and liquid chromatography-tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2004 Jan; 34(1):175-87. doi:
10.1016/j.japna.2003.08.016. [PMID: 14738932] - Dietrich von Stechow, Susan Fish, Dror Yahalom, Itai Bab, Michael Chorev, Ralph Müller, Joseph M Alexander. Does simvastatin stimulate bone formation in vivo?.
BMC musculoskeletal disorders.
2003 Apr; 4(?):8. doi:
10.1186/1471-2474-4-8. [PMID: 12718758] - Richard J Cenedella, Jerome R Kuszak, Kristin J Al-Ghoul, Shucun Qin, Patricia S Sexton. Discordant expression of the sterol pathway in lens underlies simvastatin-induced cataracts in Chbb: Thom rats.
Journal of lipid research.
2003 Jan; 44(1):198-211. doi:
10.1194/jlr.m200002-jlr200. [PMID: 12518039] - Thomayant Prueksaritanont, Jamie J Zhao, Bennett Ma, Brad A Roadcap, Cuyue Tang, Yue Qiu, Lida Liu, Jiunn H Lin, Paul G Pearson, Thomas A Baillie. Mechanistic studies on metabolic interactions between gemfibrozil and statins.
The Journal of pharmacology and experimental therapeutics.
2002 Jun; 301(3):1042-51. doi:
10.1124/jpet.301.3.1042. [PMID: 12023536] - C Kyrklund, J T Backman, K T Kivistö, M Neuvonen, J Laitila, P J Neuvonen. Rifampin greatly reduces plasma simvastatin and simvastatin acid concentrations.
Clinical pharmacology and therapeutics.
2000 Dec; 68(6):592-7. doi:
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Journal of mass spectrometry : JMS.
2000 Sep; 35(9):1133-43. doi:
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Journal of pharmaceutical and biomedical analysis.
2000 Aug; 23(2-3):323-40. doi:
10.1016/s0731-7085(00)00309-5. [PMID: 10933525] - J T Backman, C Kyrklund, K T Kivistö, J S Wang, P J Neuvonen. Plasma concentrations of active simvastatin acid are increased by gemfibrozil.
Clinical pharmacology and therapeutics.
2000 Aug; 68(2):122-9. doi:
10.1067/mcp.2000.108507. [PMID: 10976543] - J J Lilja, K T Kivistö, P J Neuvonen. Grapefruit juice-simvastatin interaction: effect on serum concentrations of simvastatin, simvastatin acid, and HMG-CoA reductase inhibitors.
Clinical pharmacology and therapeutics.
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