Ethacrynic acid (BioDeep_00000017988)
human metabolite blood metabolite
代谢物信息卡片
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
化学式: C13H12Cl2O4 (302.01126120000004)
中文名称: 利尿酸
谱图信息:
最多检出来源 Danio rerio(blood) 32.14%
分子结构信息
SMILES: C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
InChI: InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)
描述信息
A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic. [PubChem]
C - Cardiovascular system > C03 - Diuretics > C03C - High-ceiling diuretics > C03CC - Aryloxyacetic acid derivatives
C78275 - Agent Affecting Blood or Body Fluid > C448 - Diuretic > C49184 - Loop Diuretic
D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents
D045283 - Natriuretic Agents > D004232 - Diuretics
D004791 - Enzyme Inhibitors
同义名列表
35 个代谢物同义名
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid; (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid; (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetate; Methylenebutyrylphenoxyacetic acid; Methylenebutyrylphenoxyacetate; Ethacrynic acid, sodium salt; Sodium, ethacrynate; Ethacrynate sodium; Acidum etacrynicum; Acide etacrynique; Acid, ethacrinic; Ethacryinic acid; Acido etacrinico; Acid, ethacrynic; Ethacrinic acid; ETHACRYNIC ACID; Acid, etacrynic; Etacrynic acid; Etakrinic acid; Etacrinic acid; Ethacrynate; Etacrinate; Hydromedin; Hidromedin; Etacrynate; Taladren; Crinuryl; Edecrina; Endecril; Edecrin; Otacril; Edecril; Reomax; Uregit; Mingit
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:4876
- PubChem: 3278
- HMDB: HMDB0015039
- DrugBank: DB00903
- ChEMBL: CHEMBL456
- Wikipedia: Etacrynic_acid
- MeSH: Ethacrynic Acid
- chemspider: 3163
- CAS: 58-54-8
- PMhub: MS000001553
- RefMet: Ethacrynic acid
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)
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
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BMC pharmacology & toxicology.
2022 06; 23(1):35. doi:
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Protein & cell.
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2004 Mar; 308(3):1021-9. doi:
10.1124/jpet.103.059139. [PMID: 14610216] - Naoto Shikano, Yoshikatsu Kanai, Keiichi Kawai, Nobuyoshi Ishikawa, Hitoshi Endou. Transport of 99mTc-MAG3 via rat renal organic anion transporter 1.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2004 Jan; 45(1):80-5. doi:
. [PMID: 14734677] - Heleen M Wortelboer, Mustafa Usta, Astrid E van der Velde, Marelle G Boersma, Bert Spenkelink, Jelmer J van Zanden, Ivonne M C M Rietjens, Peter J van Bladeren, Nicole H P Cnubben. Interplay between MRP inhibition and metabolism of MRP inhibitors: the case of curcumin.
Chemical research in toxicology.
2003 Dec; 16(12):1642-51. doi:
10.1021/tx034101x. [PMID: 14680379] - Joseph M Alisky, Thomas F Tuttle. Ethacrynic acid can be effective for refractory congestive heart failure and ascites.
Southern medical journal.
2003 Nov; 96(11):1148-50. doi:
10.1097/01.smj.0000082004.40613.d7. [PMID: 14632366] - Dalian Ding, Sandra L McFadden, Richard W Browne, Richard J Salvi. Late dosing with ethacrynic acid can reduce gentamicin concentration in perilymph and protect cochlear hair cells.
Hearing research.
2003 Nov; 185(1-2):90-6. doi:
10.1016/s0378-5955(03)00258-2. [PMID: 14599696] - F Kiil, O M Sejersted. Analysis of energy metabolism and mechanism of loop diuretics in the thick ascending limb of Henle's loop in dog kidneys.
Acta physiologica Scandinavica.
2003 May; 178(1):73-82. doi:
10.1046/j.1365-201x.2003.01058.x. [PMID: 12713517] - Masayuki Fujita, Mohammad Z Hossain. Modulation of pumpkin glutathione S-transferases by aldehydes and related compounds.
Plant & cell physiology.
2003 May; 44(5):481-90. doi:
10.1093/pcp/pcg060. [PMID: 12773634] - Rosa M F Cardoso, Douglas S Daniels, Christopher M Bruns, John A Tainer. Characterization of the electrophile binding site and substrate binding mode of the 26-kDa glutathione S-transferase from Schistosoma japonicum.
Proteins.
2003 Apr; 51(1):137-46. doi:
10.1002/prot.10345. [PMID: 12596270] - Alison R Taylor, Colin Brownlee. A novel Cl- inward-rectifying current in the plasma membrane of the calcifying marine phytoplankton Coccolithus pelagicus.
Plant physiology.
2003 Mar; 131(3):1391-400. doi:
10.1104/pp.011791. [PMID: 12644688] - Alison Hinshelwood, Gail McGarvie, Elizabeth M Ellis. Substrate specificity of mouse aldo-keto reductase AKR7A5.
Chemico-biological interactions.
2003 Feb; 143-144(?):263-9. doi:
10.1016/s0009-2797(02)00173-4. [PMID: 12604212] - Geoffrey C Wall, Dori Bigner, Steven Craig. Ethacrynic acid and the sulfa-sensitive patient.
Archives of internal medicine.
2003 Jan; 163(1):116-7. doi:
10.1001/archinte.163.1.116. [PMID: 12523926] - Mohammed Habdous, Monique Vincent-Viry, Sophie Visvikis, Gérard Siest. Rapid spectrophotometric method for serum glutathione S-transferases activity.
Clinica chimica acta; international journal of clinical chemistry.
2002 Dec; 326(1-2):131-42. doi:
10.1016/s0009-8981(02)00329-7. [PMID: 12417104] - Mümtaz Işcan, Ahmet O Ada, Tülay Coban, Nilgün Kapucuoğlu, Ahmet Aydin, Aşkin Isimer. Combined effects of cadmium and nickel on testicular xenobiotic metabolizing enzymes in rats.
Biological trace element research.
2002 Nov; 89(2):177-90. doi:
10.1385/bter:89:2:177. [PMID: 12449241] - M Pérez López, M C Nóvoa Valiñas, M J Melgar Riol. Induction of cytosolic glutathione S-transferases from Atlantic eel (Anguilla Anguilla) after intraperitoneal treatment with polychlorinated biphenyls.
The Science of the total environment.
2002 Oct; 297(1-3):141-51. doi:
10.1016/s0048-9697(02)00130-4. [PMID: 12389786] - Jianxia Guo, Ludwika Zimniak, Piotr Zimniak, John L Orchard, Shivendra V Singh. Cloning and expression of a novel Mu class murine glutathione transferase isoenzyme.
The Biochemical journal.
2002 Sep; 366(Pt 3):817-24. doi:
10.1042/bj20020041. [PMID: 12069689] - Mary-Laure Vidal, Anne Bassères, Jean-François Narbonne. Influence of temperature, pH, oxygenation, water-type and substrate on biomarker responses in the freshwater clam Corbicula fluminea (Müller).
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2002 May; 132(1):93-104. doi:
10.1016/s1532-0456(02)00051-0. [PMID: 12039689] - F Kiil. Analysis of myogenic mechanisms in renal autoregulation.
Acta physiologica Scandinavica.
2002 Apr; 174(4):347-55. doi:
10.1046/j.1365-201x.2002.00966.x. [PMID: 11942922] - K Yamamoto, Y Masubuchi, S Narimatsu, S Kobayashi, T Horie. Toxicity of ethacrynic acid in isolated rat hepatocytes.
Toxicology in vitro : an international journal published in association with BIBRA.
2002 Apr; 16(2):151-8. doi:
10.1016/s0887-2333(01)00107-2. [PMID: 11869877] - Mumtaz Iscan, Tulay Coban, Ismet Cok, Dilek Bulbul, Benay C Eke, Sema Burgaz. The organochlorine pesticide residues and antioxidant enzyme activities in human breast tumors: is there any association?.
Breast cancer research and treatment.
2002 Mar; 72(2):173-82. doi:
10.1023/a:1014828705281. [PMID: 12038708] - Stanley Mukanganyama, Mikael Widersten, Yogeshkumar S Naik, Bengt Mannervik, Julia A Hasler. Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance.
International journal of cancer.
2002 Feb; 97(5):700-5. doi:
10.1002/ijc.10054. [PMID: 11807801] - S A Menzikov, O V Menzikova. Characteristics of the plasma membrane Cl(-)-ATPase of the bream (Abramis brama) brain sensitive to the inhibitory receptor ligands.
Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections.
2002 Jan; 382(?):8-10. doi:
10.1023/a:1014409002926. [PMID: 11998762] - E P Gallagher, T S Gross, K M Sheehy. Decreased glutathione S-transferase expression and activity and altered sex steroids in Lake Apopka brown bullheads (Ameiurus nebulosus).
Aquatic toxicology (Amsterdam, Netherlands).
2001 Nov; 55(3-4):223-37. doi:
10.1016/s0166-445x(01)00158-8. [PMID: 11595311] - G T Hanke, F D Northrop, G R Devine, J H Bothwell, J M Davies. Chloride channel antagonists perturb growth and morphology of Neurospora crassa.
FEMS microbiology letters.
2001 Jul; 201(2):243-7. doi:
10.1111/j.1574-6968.2001.tb10763.x. [PMID: 11470368] - N E Pettigrew, E J Brush, R F Colman. 3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38.
Biochemistry.
2001 Jun; 40(25):7549-58. doi:
10.1021/bi002840w. [PMID: 11412109] - V Sanz-Nebot, I Toro, R Bergés, R Ventura, J Segura, J Barbosa. Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry.
Journal of mass spectrometry : JMS.
2001 Jun; 36(6):652-7. doi:
10.1002/jms.166. [PMID: 11433538] - M Machala, L Dusek, K Hilscherová, R Kubínová, P Jurajda, J Neca, R Ulrich, M Gelnar, Z Studnicková, I Holoubek. Determination and multivariate statistical analysis of biochemical responses to environmental contaminants in feral freshwater fish Leuciscus cephalus, L.
Environmental toxicology and chemistry.
2001 May; 20(5):1141-8. doi:
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British journal of pharmacology.
2001 Apr; 132(7):1581-9. doi:
10.1038/sj.bjp.0703950. [PMID: 11264253] - K Yamamoto, Y Masubuchi, S Narimatsu, S Kobayashi, T Horie. Rat liver microsomal lipid peroxidation produced during the oxidative metabolism of ethacrynic acid.
Pharmacology & toxicology.
2001 Apr; 88(4):176-80. doi:
10.1034/j.1600-0773.2001.d01-100.x. [PMID: 11322174] - P Hoarau, M Gnassia-Barelli, M Romeo, J P Girard. Differential induction of glutathione S-transferases in the clam Ruditapes decussatus exposed to organic compounds.
Environmental toxicology and chemistry.
2001 Mar; 20(3):523-9. doi:
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Biochemistry and cell biology = Biochimie et biologie cellulaire.
2001; 79(2):165-75. doi:
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Archives of toxicology.
2001 Jan; 74(11):688-94. doi:
10.1007/s002040000184. [PMID: 11218045] - K H Reid, S Z Guo, V G Iyer. Agents which block potassium-chloride cotransport prevent sound-triggered seizures in post-ischemic audiogenic seizure-prone rats.
Brain research.
2000 May; 864(1):134-7. doi:
10.1016/s0006-8993(00)02121-1. [PMID: 10793196] - X B Zhang, C C Guo, J B Xu, G L Shen, R Q Yu. A novel ethacrynic acid sensor based on a lanthanide porphyrin complex in a PVC matrix.
The Analyst.
2000 May; 125(5):867-70. doi:
10.1039/a909858e. [PMID: 10885056] - C El Adlouni, E Pinelli, B Azémar, D Zaoui, P Beaune, A Pfohl-Leszkowicz. Phenobarbital increases DNA adduct and metabolites formed by ochratoxin A: role of CYP 2C9 and microsomal glutathione-S-transferase.
Environmental and molecular mutagenesis.
2000; 35(2):123-31. doi:
10.1002/(sici)1098-2280(2000)35:2<123::aid-em7>3.3.co;2-c. [PMID: 10712746] - R G Tirona, K S Pang. Bimolecular glutathione conjugation kinetics of ethacrynic acid in rat liver: in vitro and perfusion studies.
The Journal of pharmacology and experimental therapeutics.
1999 Sep; 290(3):1230-41. doi:
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The Journal of membrane biology.
1999 Feb; 167(3):267-74. doi:
10.1007/s002329900491. [PMID: 9929379] - C Bertucci, B Nanni, P Salvadori. Reversible binding of ethacrynic acid to human serum albumin: difference circular dichroism study.
Chirality.
1999; 11(1):33-8. doi:
10.1002/(sici)1520-636x(1999)11:1<33::aid-chir6>3.0.co;2-u. [PMID: 9914651] - K T Papazisis, D Kouretas, G D Geromichalos, E Sivridis, O K Tsekreli, K A Dimitriadis, A H Kortsaris. Effects of melatonin on proliferation of cancer cell lines.
Journal of pineal research.
1998 Dec; 25(4):211-8. doi:
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