Isosorbide Mononitrate (BioDeep_00000006581)
Secondary id: BioDeep_00001867932
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 (191.043)
中文名称: 5-硝酸异山梨酯
谱图信息:
最多检出来源 Homo sapiens(blood) 60.61%
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
56 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; Isosorbide mononitrate
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
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。
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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.
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Molecular pharmacology.
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10.1124/mol.119.115964. [PMID: 31515284] - Bhavesh D Patel, Nageswararao Pulakundam, Ajit R Gadekar, Amol A Raje, Vikram Ramanathan, Rakshit Ameta. Development and validation of a chiral LC-ESI-MS/MS method for simultaneous determination of the enantiomeric metabolites isosorbide 2-mononitrate and isosorbide 5-mononitrate of isosorbide dinitrate in rat and human plasma.
Journal of pharmaceutical and biomedical analysis.
2019 Sep; 174(?):396-405. doi:
10.1016/j.jpba.2019.06.007. [PMID: 31212140] - 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.
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10.3390/ijerph7114050. [PMID: 21139876] - Elvira Tarsitano, Grazia Greco, Nicola Decaro, Francesco Nicassio, Maria Stella Lucente, Canio Buonavoglia, Maria Tempesta. Environmental monitoring and analysis of faecal contamination in an urban setting in the city of Bari (Apulia region, Italy): health and hygiene implications.
International journal of environmental research and public health.
2010 11; 7(11):3972-86. doi:
10.3390/ijerph7113972. [PMID: 21139871] - Ann C Hylton, Tanya O Ezekiel. Rhabdomyolysis in a patient receiving ranolazine and simvastatin.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.
2010 Nov; 67(21):1829-31. doi:
10.2146/ajhp090299. [PMID: 20966146] - João P S Cabral. Water microbiology. Bacterial pathogens and water.
International journal of environmental research and public health.
2010 10; 7(10):3657-703. doi:
10.3390/ijerph7103657. [PMID: 21139855] - Sara Hardell, Hanna Tilander, Gretchen Welfinger-Smith, Joanna Burger, David O Carpenter. Levels of polychlorinated biphenyls (PCBs) and three organochlorine pesticides in fish from the Aleutian Islands of Alaska.
PloS one.
2010 Aug; 5(8):e12396. doi:
10.1371/journal.pone.0012396. [PMID: 20811633] - 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] - Omar Mohamed E Abdel Salam, Amany A Sleem, Nermeen Shafee. Hepatoprotective effects of the nitric oxide donor isosorbide-5-mononitrate alone and in combination with the natural hepatoprotectant, silymarin, on carbon tetrachloride-induced hepatic injury in rats.
Inflammopharmacology.
2010 Apr; 18(2):87-94. doi:
10.1007/s10787-009-0027-7. [PMID: 20069380] - 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] - N Prakash, Kumar M Vijay, U Sunilchandra, Bh Pavithra, A Pawar. Evaluation of Testicular Toxicity Following Short-term Exposure to Cypermethrin in Albino Mice.
Toxicology international.
2010 Jan; 17(1):18-21. doi:
10.4103/0971-6580.68344. [PMID: 21042468] - Min-Hye Park, Tae-Hwan Lee, Bo-Mi Lee, Jin Hur, Dae-Hee Park. Spectroscopic and chromatographic characterization of wastewater organic matter from a biological treatment plant.
Sensors (Basel, Switzerland).
2010; 10(1):254-65. doi:
10.3390/s100100254. [PMID: 22315538] - 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] - Subhendu Bandyopadhyay, Partha P Choudhury. Leaching behaviour of pendimethalin causes toxicity towards different cultivars of Brassica juncea and Brassica campestris in sandy loam soil.
Interdisciplinary toxicology.
2009 Dec; 2(4):250-3. doi:
10.2478/v10102-009-0025-z. [PMID: 21217862] - 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] - Darren C Henstridge, Stephen J Duffy, Melissa F Formosa, Anna A Ahimastos, Bruce R Thompson, Bronwyn A Kingwell. Oral nitrate therapy does not affect glucose metabolism in healthy men.
Clinical and experimental pharmacology & physiology.
2009 Nov; 36(11):1086-92. doi:
10.1111/j.1440-1681.2009.05195.x. [PMID: 19413595] - 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] - Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance.
Journal of medicinal chemistry.
2009 Aug; 52(15):4844-52. doi:
10.1021/jm900403j. [PMID: 19445515] - Vanji Karthikeyan, Karthik Ananthasubramaniam. Coronary risk assessment and management options in chronic kidney disease patients prior to kidney transplantation.
Current cardiology reviews.
2009 Aug; 5(3):177-86. doi:
10.2174/157340309788970342. [PMID: 20676276] - Sarita Sinha, Ankita Basant, Amrita Malik, Kunwar P Singh. Multivariate modeling of chromium-induced oxidative stress and biochemical changes in plants of Pistia stratiotes L.
Ecotoxicology (London, England).
2009 Jul; 18(5):555-66. doi:
10.1007/s10646-009-0313-6. [PMID: 19396544] - Xueyan Duan, Qingfei Liu, Yu Zhang, Kaishun Bi, Xi Chen, Yiming Wang, Guoan Luo. Development of monolithic osmotic pump tablet system for isosorbide-5-mononitrate delivery and evaluation of it in vitro and in vivo.
Drug development and industrial pharmacy.
2009 Apr; 35(4):499-507. doi:
10.1080/03639040802459437. [PMID: 18979308] - Wen-chong Liu, Xiao-li Sun, Le-le Ji, Hai-bo Wang, Hai-feng Zhang, Jia Li, Lei Shi, Lin-lin Jing, Feng Gao. [Synthesis and cardioprotective effect of a novel anti-ischemic/reperfused injury compound].
Yao xue xue bao = Acta pharmaceutica Sinica.
2009 Mar; 44(3):321-6. doi:
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Medical science monitor : international medical journal of experimental and clinical research.
2009 Mar; 15(3):LE2-3. doi:
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Toxicology mechanisms and methods.
2009 Mar; 19(3):219-24. doi:
10.1080/15376510802499048. [PMID: 19750022] - Anna Goraca, Katarzyna Asłanowicz-Antkowiak. Prophylaxis with alpha-lipoic acid against lipopolysaccharide-induced brain injury in rats.
Archivum immunologiae et therapiae experimentalis.
2009 Mar; 57(2):141-6. doi:
10.1007/s00005-009-0015-z. [PMID: 19333732] - Zachary Z Brener, Igor Zhuravenko, Michael Bergman. Acute kidney injury in a patient with nontuberculous mycobacterial infections: a case report.
Cases journal.
2009 Jan; 2(1):83. doi:
10.1186/1757-1626-2-83. [PMID: 19166597] - Christopher T Migliaccio, Megan A Bergauff, Christopher P Palmer, Forrest Jessop, Curtis W Noonan, Tony J Ward. Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children.
Environmental health perspectives.
2009 Jan; 117(1):74-9. doi:
10.1289/ehp.11378. [PMID: 19165390] - Eui-Chan Jeon, Hyun-Keun Son, Jae-Hwan Sa. Emission characteristics and factors of selected odorous compounds at a wastewater treatment plant.
Sensors (Basel, Switzerland).
2009; 9(1):311-26. doi:
10.3390/s90100311. [PMID: 22389601] - 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] - Edward Kowalczyk, Maria Kopff, Jan Kowalski, Anna Kopff, Dimitri P Mikhailidis, Marcin Barylski, Maciej Banach. Effect of cardiovascular drugs on adenosine deaminase activity.
Angiology.
2008 Dec; 59(6):740-4. doi:
10.1177/0003319708323495. [PMID: 18840621] - M Oppermann, V T-V Dao, T Suvorava, M Bas, G Kojda. Effect of oral organic nitrates on expression and activity of vascular soluble guanylyl cyclase.
British journal of pharmacology.
2008 Oct; 155(3):335-42. doi:
10.1038/bjp.2008.269. [PMID: 18587420] - Anders I Seldén, Cecilia Lundholm, Niklas Johansson, Håkan Wingfors. Polychlorinated biphenyls (PCB), thyroid hormones and cytokines in construction workers removing old elastic sealants.
International archives of occupational and environmental health.
2008 Oct; 82(1):99-106. doi:
10.1007/s00420-008-0313-5. [PMID: 18350309] - Arshdeep Tindni, Kumar Gaurav, Mukta Panda. Non-healing painful ulcers in a patient with chronic kidney disease and role of sodium thiosulfate: a case report.
Cases journal.
2008 Sep; 1(1):178. doi:
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