Isosorbide Mononitrate (BioDeep_00000006581)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate

化学式: C6H9NO6 (191.04298540000002)
中文名称: 5-硝酸异山梨酯
谱图信息: 最多检出来源 Homo sapiens(blood) 85%

分子结构信息

SMILES: C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O
InChI: InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1

描述信息

Isosorbide mononitrate (ISMN), sold under the names Imdur and Monoket, among others, is an organic nitrate used principally in the prophylactic treatment of angina pectoris (ischemic chest pain). ISMN is an active metabolite of isosorbide dinitrate and exerts qualitatively similar effects. Like other organic nitrates, ISMN acts as a prodrug for its active metabolite, nitric oxide, which mediates the therapeutic action of ISMN. Nitric oxide works on both arteries and veins, but predominantly veins. Nitric oxide functions by relaxing veins and reducing the central venous pressure, thereby causing venous pooling and a decrease in the venous return to the heart, thus decreasing cardiac preload (PMID: 31643263). The net effect when administering ISMN is therefore a reduced workload for the heart and an improvement in the oxygen supply/demand balance of the myocardium. ISMN is not subject to first pass metabolism in the human liver. Detectable metabolites include isosorbide, sorbitol, and 2-glucuronide of mononitrate, which are pharmacologically inactive (PMID: 1449102). Research on ISMN as a cervical ripener to reduce time at hospital to birth is supportive (PMID: 23983763). Isosorbide mononitrate is only found in individuals who have consumed or used this drug.
C - Cardiovascular system > C01 - Cardiac therapy > C01D - Vasodilators used in cardiac diseases > C01DA - Organic nitrates
C78274 - Agent Affecting Cardiovascular System > C29707 - Vasodilating Agent
D002317 - Cardiovascular Agents > D020030 - Nitric Oxide Donors
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

同义名列表

55 个代谢物同义名

(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate; Mononitric acid disosorbide; Isosorbide mononitric acid; Mononitrato de isosorbida; Isosorbide 5-mononitrate; Isosorbide-5-mononitrate; Mononitrate disosorbide; Isosorbide Mononitrate; Isosorbidi mononitras; Isosorbide-5-nitrate; Monosorbitric acid; Monodur durules; Olicard-retard; Monosorbitrate; Monosorb XL 60; 5-ISMN durules; SCHEMBL616518; mono Mac 50D; Monocedocard; Imtric acid; Monosordil; mono Corax; Olicard 40; Monocinque; Turimonit; Orasorbil; Promocard; Monopront; Sorbimon; Sigacora; Vasdilat; Monocord; Nitramin; Monolong; Corangin; Ismexin; Olicard; Mononit; Monomax; Imtrate; Elantan; Monicor; Monoket; Medocor; Monizid; 5-ISMN; Uniket; Duride; Pertil; Imdur; monit; Ismox; ISMN; Ismo; IHD

数据库引用编号

14 个数据库交叉引用编号

ChEBI: CHEBI:6062
KEGG: C07714
KEGGdrug: D00630
PubChem: 27661
HMDB: HMDB0015155
Metlin: METLIN860
DrugBank: DB01020
ChEMBL: CHEMBL1311
Wikipedia: Isosorbide mononitrate
chemspider: 25736
CAS: 16051-77-7
PMhub: MS000019643
PubChem: 9916
NIKKAJI: J22.753F

分类词条

Isosorbides

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

9606 - Homo sapiens: -

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

Yubo Peng, Yanfang Li, Mengmeng Chen, Junying Song, Zhili Jiang, Shutian Shi. High-dose nitrate therapy recovers the expression of subtypes α1 and β-adrenoceptors and Ang II receptors of the renal cortex in rats with myocardial infarction-induced heart failures. BMC cardiovascular disorders. 2020 02; 20(1):99. doi: 10.1186/s12872-020-01353-z. [PMID: 32106816]
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Zuoliang Liu, Bikui Zhang, Xin Guo, Lei Chen, Dongyang Yi, Junzi Cong, Ren Guo. CGRP mediate the isosorbide-5-mononitrate cardiovascular response in healthy Chinese male volunteers through a XOR-independent pathway. International journal of clinical pharmacology and therapeutics. 2015 Apr; 53(4):325-34. doi: 10.5414/cp202178. [PMID: 25740261]
Ning Li, Chun-lan Li, Ning-wei Lu, Yu-ming Dong. A novel micellar per aqueous liquid chromatographic method for simultaneous determination of diltiazem hydrochloride, metoprolol tartrate and isosorbide mononitrate in human serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Sep; 967(?):90-7. doi: 10.1016/j.jchromb.2014.07.019. [PMID: 25086418]
Z Jiang, C Wei, Z Sun, J Guo, R Li, R Zhang, G Yuan, R Guo. A simple and sensitive gas chromatography method for determination of isosorbide dinitrate and its metabolites in human plasma: application to pharmacokinetics study on oral spray. Drug research. 2014 Feb; 64(2):73-8. doi: 10.1055/s-0033-1351286. [PMID: 23904215]
Camille Jardeleza, Shasha Rao, Benjamin Thierry, Pratik Gajjar, Sarah Vreugde, Clive A Prestidge, Peter-John Wormald. Liposome-encapsulated ISMN: a novel nitric oxide-based therapeutic agent against Staphylococcus aureus biofilms. PloS one. 2014; 9(3):e92117. doi: 10.1371/journal.pone.0092117. [PMID: 24658315]
Fatih Tarhan, Osman Çelik, Çağatay Tosun, Gökhan Faydacı, Bilal Eryıldırım. Comparison of the efficacy of isosorbide mononitrate and doxazosin in the treatment of lower urinary tract symptoms and benign prostatic hyperplasia: a randomized clinical trial. Urologia internationalis. 2014; 93(1):17-21. doi: 10.1159/000357034. [PMID: 24643055]
Jiangtao Lai, Bifeng Wu, Jian Sun, Yunpeng Shang, Jianhua Zhu. Long-term isosorbide mononitrate treatment impairs endothelial function in patients with coronary artery disease. Coronary artery disease. 2013 Nov; 24(7):566-71. doi: 10.1097/mca.0000000000000029. [PMID: 23994882]
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Christopher Ddidigwu Nwani, Wazir Singh Lakra, Naresh Sahebrao Nagpure, Ravindra Kumar, Basdeo Kushwaha, Satish Kumar Srivastava. Toxicity of the herbicide atrazine: effects on lipid peroxidation and activities of antioxidant enzymes in the freshwater fish Channa punctatus (Bloch). International journal of environmental research and public health. 2010 08; 7(8):3298-312. doi: 10.3390/ijerph7083298. [PMID: 20948961]
Terri A Long, Hironaka Tsukagoshi, Wolfgang Busch, Brett Lahner, David E Salt, Philip N Benfey. The bHLH transcription factor POPEYE regulates response to iron deficiency in Arabidopsis roots. The Plant cell. 2010 Jul; 22(7):2219-36. doi: 10.1105/tpc.110.074096. [PMID: 20675571]
Sridhar R Vasudevan, Alexander M Lewis, Jennifer W Chan, Claire L Machin, Debroshi Sinha, Antony Galione, Grant C Churchill. The calcium-mobilizing messenger nicotinic acid adenine dinucleotide phosphate participates in sperm activation by mediating the acrosome reaction. The Journal of biological chemistry. 2010 Jun; 285(24):18262-9. doi: 10.1074/jbc.m109.087858. [PMID: 20400502]
Pietro Manuel Ferraro, Stefano Costanzi, Alessandro Naticchia, Antonio Sturniolo, Giovanni Gambaro. Low level exposure to cadmium increases the risk of chronic kidney disease: analysis of the NHANES 1999-2006. BMC public health. 2010 Jun; 10(?):304. doi: 10.1186/1471-2458-10-304. [PMID: 20525263]
Dae Won Jun, Jin Hee Park, Yoo Sin Park, Ju-Seop Kang, Eun Kyung Kim, Kyung Tae Kim, Byoung Kwan Son, Seong Hwan Kim, Yun Ju Jo, Young Sook Park. The role of nitric oxide in the expression of renal aquaporin 2 in a cirrhotic rat model: does an AVP-independent mechanism exist for the regulation of AQP2 expression?. Digestive diseases and sciences. 2010 May; 55(5):1296-304. doi: 10.1007/s10620-009-0852-y. [PMID: 19517235]
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Nalini Eswaran, Sriram Parameswaran, Balaji Sathram, Bhagyam Anantharaman, Raja Krishna Kumar G, Sudhakar Johnson Tangirala. Yeast functional screen to identify genetic determinants capable of conferring abiotic stress tolerance in Jatropha curcas. BMC biotechnology. 2010 Mar; 10(?):23. doi: 10.1186/1472-6750-10-23. [PMID: 20302659]
Shirley Telles, Visweswaraiah K Naveen, Acharya Balkrishna. Serum leptin, cholesterol and blood glucose levels in diabetics following a yoga and diet change program Comment to: Statins and beta-cell function Lei Qian, Lihong Xu, Yi Lin, Yongde Peng Med Sci Monit, 2010; 16(1): HY1-2. Medical science monitor : international medical journal of experimental and clinical research. 2010 Mar; 16(3):LE4-5. doi: NULL. [PMID: 20190692]
Gabriel Krouk, Piotr Mirowski, Yann LeCun, Dennis E Shasha, Gloria M Coruzzi. Predictive network modeling of the high-resolution dynamic plant transcriptome in response to nitrate. Genome biology. 2010; 11(12):R123. doi: 10.1186/gb-2010-11-12-r123. [PMID: 21182762]
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Shirley Telles. Practicing yoga postures possibly increases relaxation and reduces anxiety comment to: Formulations of dietary supplements and herbal extracts for relaxation and anxiolytic action: Relarian, Benjamin S. Weeks, Med Sci Monit, 2009; 15(11): RA256-262. Medical science monitor : international medical journal of experimental and clinical research. 2009 Dec; 15(12):LE9. doi: ". [PMID: 19946249]
Dragan R Milićević, Milijan Jovanović, Verica B Jurić, Zoran I Petrović, Srdan M Stefanović. Toxicological assessment of toxic element residues in swine kidney and its role in public health risk assessment. International journal of environmental research and public health. 2009 12; 6(12):3127-42. doi: 10.3390/ijerph6123127. [PMID: 20049251]
Aline Philibert, Harold Schwartz, Donna Mergler. An exploratory study of diabetes in a First Nation community with respect to serum concentrations of p,p'-DDE and PCBs and fish consumption. International journal of environmental research and public health. 2009 12; 6(12):3179-89. doi: 10.3390/ijerph6123179. [PMID: 20049255]
Brenda C M de Winter, Teun van Gelder, Ferdi Sombogaard, Leslie M Shaw, Reinier M van Hest, Ron A A Mathot. Pharmacokinetic role of protein binding of mycophenolic acid and its glucuronide metabolite in renal transplant recipients. Journal of pharmacokinetics and pharmacodynamics. 2009 Dec; 36(6):541-64. doi: 10.1007/s10928-009-9136-6. [PMID: 19904584]
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Adedigbo A Fasanmade, Omoniyi J Adedokun, Joyce Ford, Danika Hernandez, Jewel Johanns, Chuanpu Hu, Hugh M Davis, Honghui Zhou. Population pharmacokinetic analysis of infliximab in patients with ulcerative colitis. European journal of clinical pharmacology. 2009 Dec; 65(12):1211-28. doi: 10.1007/s00228-009-0718-4. [PMID: 19756557]
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Ashish Kumar, Sanjeev Kumar Jha, Praveen Sharma, Saroj Dubey, Pankaj Tyagi, Barjesh Chander Sharma, Shiv Kumar Sarin. Addition of propranolol and isosorbide mononitrate to endoscopic variceal ligation does not reduce variceal rebleeding incidence. Gastroenterology. 2009 Sep; 137(3):892-901, 901.e1. doi: 10.1053/j.gastro.2009.05.049. [PMID: 19481079]
Pratima Tripathi, M Chandra, Mithilesh K Misra. Oral administration of L-arginine in patients with angina or following myocardial infarction may be protective by increasing plasma superoxide dismutase and total thiols with reduction in serum cholesterol and xanthine oxidase. Oxidative medicine and cellular longevity. 2009 Sep; 2(4):231-7. doi: 10.4161/oxim.2.4.9233. [PMID: 20716909]
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Gayane Martirosian, Alicja Ekiel, Małgorzata Aptekorz, Beata Kazek, Elzbieta Marszał, Ewa Jankowska-Steifer, Stanisław Moskalewski. Intestinal anaerobic bacteria and autistic mind: is there some relations? Comment to: the autistic mind: a case study. Katarzyna Markiewicz, Bruce Duncan MacQueen. Med Sci Monit, 2009; 15(1): CS5-13. Medical science monitor : international medical journal of experimental and clinical research. 2009 Mar; 15(3):LE2-3. doi: NULL. [PMID: 19247253]
Xichun Zhang, Fahe Chen, Zhiyong Huang. Apoptosis induced by acrylamide is suppressed in a 21.5\% fat diet through caspase-3-independent pathway in mice testis. Toxicology mechanisms and methods. 2009 Mar; 19(3):219-24. doi: 10.1080/15376510802499048. [PMID: 19750022]
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Nicolas Pichaud, Jocelyne Pellerin, Michel Fournier, Sophie Gauthier-Clerc, Pascal Rioux, Emilien Pelletier. Oxidative stress and immunologic responses following a dietary exposure to PAHs in Mya arenaria. Chemistry Central journal. 2008 Dec; 2(?):23. doi: 10.1186/1752-153x-2-23. [PMID: 19055737]
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