Etodolac (BioDeep_00000001784)

 

Secondary id: BioDeep_00000397851

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid

化学式: C17H21NO3 (287.1521356)
中文名称: 依托度酸
谱图信息: 最多检出来源 Homo sapiens(blood) 28.57%

分子结构信息

SMILES: CCC1=C2C(=CC=C1)C3=C(N2)C(OCC3)(CC)CC(=O)O
InChI: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)

描述信息

Etodolac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis. Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 – 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.
M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AB - Acetic acid derivatives and related substances
D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors
D004791 - Enzyme Inhibitors > D016861 - Cyclooxygenase Inhibitors > D052246 - Cyclooxygenase 2 Inhibitors
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D000893 - Anti-Inflammatory Agents
KEIO_ID E034; [MS2] KO008956
KEIO_ID E034

同义名列表

26 个代谢物同义名

(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid; (+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid; (+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate; 1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acid; (1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetate; 1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid; 1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid; 2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid; 1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetate; 1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate; 1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetate; Etodolac, monosodium salt, (+-) isomer; Etodolac, monosodium salt, (S)-isomer; Etodolac, monosodium salt; Etodolac, (+-)-isomer; Etodolac, (-)-isomer; Etodolac, (S)-isomer; Acid, etodolic; ETODOLIC ACID; Etodolacum; Etodolaco; ETODOLate; Ultradol; etodolac; Ramodar; Lodine



数据库引用编号

28 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

1 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(1)

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。



文献列表

  • Poonam Patil, Atul Shirkhedkar. Nanostructured Etodolac Carriers in Transdermal Gel: Optimization and Characterization. Pharmaceutical nanotechnology. 2023 Jun; 11(3):276-293. doi: 10.2174/2211738511666230111110340. [PMID: 36635925]
  • Anna Czajkowska-Kośnik, Emilia Szymańska, Katarzyna Winnicka. Nanostructured Lipid Carriers (NLC)-Based Gel Formulations as Etodolac Delivery: From Gel Preparation to Permeation Study. Molecules (Basel, Switzerland). 2022 Dec; 28(1):. doi: 10.3390/molecules28010235. [PMID: 36615429]
  • Marwa Ibrahim Helmy, Samah Sabry Saad, Maha Abdelmonem Hegazy, Ahmed Salah Fayed. Sensitive and selective LC-MS/MS for the determination of tolperisone and etodolac in human plasma and application to a pharmacokinetic study. Journal of separation science. 2022 May; 45(10):1646-1655. doi: 10.1002/jssc.202100991. [PMID: 35233941]
  • Syed Nazrin Ruhina Rahman, Oly Katari, Datta Maroti Pawde, Gopi Sumanth Bhaskar Boddeda, Abhinab Goswami, Srinivasa Rao Mutheneni, Tamilvanan Shunmugaperumal. Application of Design of Experiments® Approach-Driven Artificial Intelligence and Machine Learning for Systematic Optimization of Reverse Phase High Performance Liquid Chromatography Method to Analyze Simultaneously Two Drugs (Cyclosporin A and Etodolac) in Solution, Human Plasma, Nanocapsules, and Emulsions. AAPS PharmSciTech. 2021 May; 22(4):155. doi: 10.1208/s12249-021-02026-6. [PMID: 33987739]
  • 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]
  • Michael R Duff, Scott A Gabel, Lars C Pedersen, Eugene F DeRose, Juno M Krahn, Elizabeth E Howell, Robert E London. The Structural Basis for Nonsteroidal Anti-Inflammatory Drug Inhibition of Human Dihydrofolate Reductase. Journal of medicinal chemistry. 2020 08; 63(15):8314-8324. doi: 10.1021/acs.jmedchem.0c00546. [PMID: 32658475]
  • Sonia T Hassib, Ghaneya S Hassan, Asmaa A El-Zaher, Marwa A Fouad, Omnia A Abd El-Ghafar, Enas A Taha. Synthesis and biological evaluation of new prodrugs of etodolac and tolfenamic acid with reduced ulcerogenic potential. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2019 Dec; 140(?):105101. doi: 10.1016/j.ejps.2019.105101. [PMID: 31639436]
  • 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]
  • Malek Hassan, Usama Alshana. Switchable-hydrophilicity solvent liquid-liquid microextraction of non-steroidal anti-inflammatory drugs from biological fluids prior to HPLC-DAD determination. Journal of pharmaceutical and biomedical analysis. 2019 Sep; 174(?):509-517. doi: 10.1016/j.jpba.2019.06.023. [PMID: 31238298]
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  • Noha Khalifa Abo Aasy, Doaa Ragab, Marwa Ahmed Sallam, Doaa A Abdelmonsif, Rania G Aly, Kadria A Elkhodairy. A comparative study: the prospective influence of nanovectors in leveraging the chemopreventive potential of COX-2 inhibitors against skin cancer. International journal of nanomedicine. 2019; 14(?):7561-7581. doi: 10.2147/ijn.s218905. [PMID: 31571864]
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  • Yin Zhou, Paula Hertel, Jennifer Cu. Case 5: Large Amounts of Urine Bilirubin on Urine Dipstick in a 14-year-old Girl. Pediatrics in review. 2017 Sep; 38(9):440. doi: 10.1542/pir.2015-0068. [PMID: 28864738]
  • Il-Dong Song, Ju-Seop Kang, Hyun-Jin Kim, Se-Mi Kim, Dong-Xu Zhao, Shin-Hee Kim, Min-Young Chun, Kyu-Hyun Lee. Quantification of Etodolac in Human Plasma for Pharmacokinetics and Bioequivalence Studies in 27 Korean Subjects. Drug metabolism letters. 2017; 10(4):286-294. doi: 10.2174/1872312811666170116151004. [PMID: 28093968]
  • S Sarıözkan, G Türk, P Çıkla-Süzgün, M Güvenç, A Yüce, A H Yay, F Cantürk, Ş G Küçükgüzel. Effect of etodolac hydrazone, a new compound synthesised from etodolac, on spermatozoon quality, testicular lipid peroxidation, apoptosis and spermatozoon DNA integrity. Andrologia. 2016 Mar; 48(2):177-88. doi: 10.1111/and.12429. [PMID: 25929857]
  • Carolina de Miranda Silva, Adriana Rocha, Eduardo Tozatto, Lucienir Maria da Silva, Eduardo Antônio Donadi, Vera Lucia Lanchote. Enantioselective analysis of etodolac in human plasma by LC-MS/MS: Application to clinical pharmacokinetics. Journal of pharmaceutical and biomedical analysis. 2016 Feb; 120(?):120-6. doi: 10.1016/j.jpba.2015.12.009. [PMID: 26723001]
  • Ismail I Hewala, Marwa S Moneeb, Hatem A Elmongy, Abdel-Aziz M Wahbi. Enantioselective HPLC-DAD method for the determination of etodolac enantiomers in tablets, human plasma and application to comparative pharmacokinetic study of both enantiomers after a single oral dose to twelve healthy volunteers. Talanta. 2014 Dec; 130(?):506-17. doi: 10.1016/j.talanta.2014.07.011. [PMID: 25159440]
  • Askin Ender Topal, Hasan Akkoc, Ilker Kelle, Sedat Yilmaz, Derya Topal, Murat Akkus. Impact of N-acetylcysteine and etodolac treatment on systolic and diastolic function in a rat model of myocardial steatosis induced by high-fat-diet. Endocrine, metabolic & immune disorders drug targets. 2014; 14(4):313-9. doi: 10.2174/1871530314666141028144702. [PMID: 25348332]
  • Shenglan Wang, Yi Dai, Yoko Kogure, Satoshi Yamamoto, Wensheng Zhang, Koichi Noguchi. Etodolac activates and desensitizes transient receptor potential ankyrin 1. Journal of neuroscience research. 2013 Dec; 91(12):1591-8. doi: 10.1002/jnr.23274. [PMID: 24027177]
  • Marina Borges, Rivaldo Marini Filho, Cecília Braga Laposy, Priscylla Tatiana Chalfun Guimarães-Okamoto, Marina Platzeck Chaves, André Nanny Le Sueur Vieira, Alessandra Melchert. Nonsteroidal anti-inflammatory therapy: changes on renal function of healthy dogs. Acta cirurgica brasileira. 2013 Dec; 28(12):842-7. doi: 10.1590/s0102-86502013001200006. [PMID: 24316857]
  • Ahmed Abd-Elbary, Mina Ibrahim Tadros, Ahmed Adel Alaa-Eldin. Sucrose stearate-enriched lipid matrix tablets of etodolac: modulation of drug release, diffusional modeling and structure elucidation studies. AAPS PharmSciTech. 2013 Jun; 14(2):656-68. doi: 10.1208/s12249-013-9951-3. [PMID: 23572253]
  • Hiroshi Imamura, Jiro Hata, Ai Iida, Noriaki Manabe, Ken Haruma. Evaluating the effects of diclofenac sodium and etodolac on renal hemodynamics with contrast-enhanced ultrasonography: a pilot study. European journal of clinical pharmacology. 2013 Feb; 69(2):161-5. doi: 10.1007/s00228-012-1336-0. [PMID: 22732768]
  • Katsuhito Miyazawa, Yoshitaka Takahashi, Nobuyo Morita, Manabu T Moriyama, Takeo Kosaka, Matomo Nishio, Tanihiro Yoshimoto, Koji Suzuki. Cyclooxygenase 2 and prostaglandin E2 regulate the attachment of calcium oxalate crystals to renal epithelial cells. International journal of urology : official journal of the Japanese Urological Association. 2012 Oct; 19(10):936-43. doi: 10.1111/j.1442-2042.2012.03060.x. [PMID: 22640700]
  • P Mehta, M Lukacs, S M Abraham. Normal in the blood, abnormal in the urine. QJM : monthly journal of the Association of Physicians. 2012 Oct; 105(10):1001-2. doi: 10.1093/qjmed/hcr164. [PMID: 21880696]
  • Kathryn K Surdyk, Dawn L Sloan, Scott A Brown. Renal effects of carprofen and etodolac in euvolemic and volume-depleted dogs. American journal of veterinary research. 2012 Sep; 73(9):1485-90. doi: 10.2460/ajvr.73.9.1485. [PMID: 22924732]
  • Yukiko Nozawa, Ayako Sato, Hoglan Piao, Tetsuo Morioka, Ichiei Narita, Takashi Oite. The effect of renal administration of a selective cyclooxygenase-2 inhibitor or stable prostaglandin I2 analog on the progression of sclerotic glomerulonephritis in rats. Clinical and experimental nephrology. 2012 Apr; 16(2):221-30. doi: 10.1007/s10157-011-0558-2. [PMID: 22147282]
  • Ahmed Abd-Elbary, Mina Ibrahim Tadros, Ahmed Adel Alaa-Eldin. Development and in vitro/in vivo evaluation of etodolac controlled porosity osmotic pump tablets. AAPS PharmSciTech. 2011 Jun; 12(2):485-95. doi: 10.1208/s12249-011-9608-z. [PMID: 21479749]
  • Valentina L Kouznetsova, Igor F Tsigelny, Megha A Nagle, Sanjay K Nigam. Elucidation of common pharmacophores from analysis of targeted metabolites transported by the multispecific drug transporter-Organic anion transporter1 (Oat1). Bioorganic & medicinal chemistry. 2011 Jun; 19(11):3320-40. doi: 10.1016/j.bmc.2011.04.045. [PMID: 21571536]
  • Yuuki Akagi, Yuta Nio, Shuji Shimada, Takao Aoyama. Influence of nonsteroidal anti-inflammatory drugs on the antiplatelet effects of aspirin in rats. Biological & pharmaceutical bulletin. 2011; 34(2):233-7. doi: 10.1248/bpb.34.233. [PMID: 21415533]
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  • Kimihiko Yanaoka, Masashi Oka, Noriko Yoshimura, Hisanobu Deguchi, Chizu Mukoubayashi, Shotaro Enomoto, Takao Maekita, Izumi Inoue, Kazuki Ueda, Hirotoshi Utsunomiya, Mikitaka Iguchi, Hideyuki Tamai, Mitsuhiro Fujishiro, Yasushi Nakamura, Tetsuya Tsukamoto, Kenichi Inada, Tatsuya Takeshita, Masao Ichinose. Preventive effects of etodolac, a selective cyclooxygenase-2 inhibitor, on cancer development in extensive metaplastic gastritis, a Helicobacter pylori-negative precancerous lesion. International journal of cancer. 2010 Mar; 126(6):1467-73. doi: 10.1002/ijc.24862. [PMID: 19711347]
  • Nahla S Barakat. Enhanced oral bioavailability of etodolac by self-emulsifying systems: in-vitro and in-vivo evaluation. The Journal of pharmacy and pharmacology. 2010 Feb; 62(2):173-80. doi: 10.1211/jpp.62.02.0004. [PMID: 20487196]
  • Savita Vyas, Piyush Trivedi, Subhash Chandra Chaturvedi. Dextran-etodolac conjugates: synthesis, in vitro and in vivo evaluation. Acta poloniae pharmaceutica. 2009 Mar; 66(2):201-6. doi: NULL. [PMID: 19719056]
  • Marjo J Karjalainen, Pertti J Neuvonen, Janne T Backman. In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. Basic & clinical pharmacology & toxicology. 2008 Aug; 103(2):157-65. doi: 10.1111/j.1742-7843.2008.00252.x. [PMID: 18816299]
  • Mojca Brunskole, Bogdan Stefane, Karmen Zorko, Marko Anderluh, Jure Stojan, Tea Lanisnik Rizner, Stanislav Gobec. Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: synthesis of artificial substrate, homology modelling and initial screening. Bioorganic & medicinal chemistry. 2008 Jun; 16(11):5881-9. doi: 10.1016/j.bmc.2008.04.066. [PMID: 18482840]
  • Yin-Xiu Jin, Yi-Hong Tang, Su Zeng. Analysis of flurbiprofen, ketoprofen and etodolac enantiomers by pre-column derivatization RP-HPLC and application to drug-protein binding in human plasma. Journal of pharmaceutical and biomedical analysis. 2008 Apr; 46(5):953-8. doi: 10.1016/j.jpba.2008.01.038. [PMID: 18329215]
  • Hyun-Soo Lee, Il-Mo Kang, Heon-Woo Lee, Ji-Hyung Seo, Ju-Hee Ryu, Sang-Jun Choi, Myung-Jae Lee, Seo-Young Jeong, Young-Wuk Cho, Kyung-Tae Lee. Development and validation of a high performance liquid chromatography-tandem mass spectrometry for the determination of etodolac in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Feb; 863(1):158-62. doi: 10.1016/j.jchromb.2007.11.032. [PMID: 18218344]
  • Marlene Lúcio, Helena Ferreira, José L F C Lima, Salette Reis. Use of liposomes as membrane models to evaluate the contribution of drug-membrane interactions to antioxidant properties of etodolac. Redox report : communications in free radical research. 2008; 13(5):225-36. doi: 10.1179/135100008x308939. [PMID: 18796242]
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