Ondansetron (BioDeep_00000002819)

human metabolite Chemicals and Drugs

代谢物信息卡片

9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one

化学式: C18H19N3O (293.1528044)
中文名称: 昂丹司琼, 恩丹西酮
谱图信息: 最多检出来源 Escherichia coli(natural_products) 60.53%

分子结构信息

SMILES: CC1=NC=CN1CC2CCC3=C(C2=O)C4=CC=CC=C4N3C
InChI: InChI=1S/C18H19N3O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2/h3-6,9-10,13H,7-8,11H2,1-2H3

描述信息

Ondansetron is a well tolerated drug with few side effects. Headache, constipation, and dizziness are the most commonly reported side effects associated with its use. There have been no significant drug interactions reported with this drugs use. It is broken down by the hepatic cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system; Ondansetron is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors; A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties; Ondansetron (INN) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors. [HMDB]
Ondansetron is a well tolerated drug with few side effects. Headache, constipation, and dizziness are the most commonly reported side effects associated with its use. There have been no significant drug interactions reported with this drugs use. It is broken down by the hepatic cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system; Ondansetron is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors; A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties; Ondansetron (INN) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors.
A - Alimentary tract and metabolism > A04 - Antiemetics and antinauseants > A04A - Antiemetics and antinauseants > A04AA - Serotonin (5ht3) antagonists
C78272 - Agent Affecting Nervous System > C66885 - Serotonin Antagonist > C94726 - 5-HT3 Receptor Antagonist
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent
D005765 - Gastrointestinal Agents > D000932 - Antiemetics
D003879 - Dermatologic Agents > D000982 - Antipruritics
CONFIDENCE standard compound; INTERNAL_ID 2746
CONFIDENCE standard compound; INTERNAL_ID 8525
D002491 - Central Nervous System Agents
Ondansetron (GR 38032; SN 307) is a highly selective 5-HT3 receptor antagonist, with IC50 value of 103 pM. Ondansetron exerts antiemetic effects by antagonizing 5-HT receptor located on local neurons in the peripheral and central nervous system. Ondansetron suppresses nausea and vomiting caused by chemotherapy and radiation therapy. Ondansetron has orally bioactivity[1][2][3][4][5][6][7][8].

同义名列表

18 个代谢物同义名

9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one; Dihydrate, ondansetron monohydrochloride; Monohydrochloride dihydrate, ondansetron; Ondansetron monohydrochloride dihydrate; Monohydrochloride, ondansetron; Ondansetron monohydrochloride; Hydrochloride, ondansetron; Ondansetron, (+,-)-isomer; Ondansetron hydrochloride; Ondansetron, (R)-isomer; Ondansetron, (S)-isomer; ondansetron; Zofran odt; Zophren; Zofran; Zudan; GR 38032; SN 307

数据库引用编号

27 个数据库交叉引用编号

ChEBI: CHEBI:7773
KEGG: C07325
KEGGdrug: D00456
PubChem: 4595
HMDB: HMDB0005035
Metlin: METLIN1646
DrugBank: DB00904
ChEMBL: CHEMBL46
Wikipedia: Ondansetron
MeSH: Ondansetron
foodb: FDB023602
chemspider: 4434
CAS: 116002-70-1
CAS: 99614-02-5
MoNA: AU274602
MoNA: AU274604
MoNA: AU274605
MoNA: AU274603
MoNA: AU274606
MoNA: SM852501
MoNA: AU274601
PMhub: MS000006059
PubChem: 9533
PDB-CCD: S87
NIKKAJI: J245.610I
RefMet: Ondansetron
medchemexpress: HY-B0002B

分类词条

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

Kathleen M Job, André Dallmann, Samuel Parry, George Saade, David M Haas, Brenna Hughes, Pamela Berens, Jia-Yu Chen, Christina Fu, Kelsey Humphrey, Christoph Hornik, Stephen Balevic, Kanecia Zimmerman, Kevin Watt. Development of a Generic Physiologically-Based Pharmacokinetic Model for Lactation and Prediction of Maternal and Infant Exposure to Ondansetron via Breast Milk. Clinical pharmacology and therapeutics. 2022 05; 111(5):1111-1120. doi: 10.1002/cpt.2530. [PMID: 35076931]
Masato Aoyama, Minami Shioya, Yume Tsukamoto, Hitomi Hasegawa, Shoei Sugita. The effects of cisplatin, an emetic agent, on behavior and plasma cortisol levels in goats. Animal science journal = Nihon chikusan Gakkaiho. 2021 Dec; 92(1):e13607. doi: 10.1111/asj.13607. [PMID: 34318567]
Lili Tao, Shiyu Zhou, Ping Chang, Shengli An. Effects of ondansetron use on outcomes of acute kidney injury in critically ill patients: An analysis based on the MIMIC-IV database. Journal of critical care. 2021 12; 66(?):117-122. doi: 10.1016/j.jcrc.2021.07.015. [PMID: 34509800]
Ahmad Qasem, Abed Elrahman Naser, Saleh A Naser. Enteropathogenic infections modulate intestinal serotonin transporter (SERT) function by activating Toll-like receptor 2 (TLR-2) in Crohn's disease. Scientific reports. 2021 11; 11(1):22624. doi: 10.1038/s41598-021-02050-3. [PMID: 34799637]
Derek Blevins, Chamindi Seneviratne, Xin-Qun Wang, Bankole A Johnson, Nassima Ait-Daoud. A randomized, double-blind, placebo-controlled trial of ondansetron for the treatment of cocaine use disorder with post hoc pharmacogenetic analysis. Drug and alcohol dependence. 2021 11; 228(?):109074. doi: 10.1016/j.drugalcdep.2021.109074. [PMID: 34600264]
Lucia You, Shamsa Shafi, Gary Soffer. Concomitant cow's milk and beef food protein-induced enterocolitis syndrome in a young infant. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology. 2021 10; 127(4):504-505. doi: 10.1016/j.anai.2021.06.009. [PMID: 34153445]
Mitsuhiro Goda, Masaya Kanda, Toshihiko Yoshioka, Ami Yoshida, Yoichi Murai, Yoshito Zamami, Fuka Aizawa, Takahiro Niimura, Hirofumi Hamano, Naoto Okada, Kenta Yagi, Masayuki Chuma, Yuki Izawa-Ishizawa, Keisuke Ishizawa. Effects of 5-HT₃ receptor antagonists on cisplatin-induced kidney injury. Clinical and translational science. 2021 09; 14(5):1906-1916. doi: 10.1111/cts.13045. [PMID: 33982438]
Parniyan Goodarzi, Mohammad Habibi, Kennedy Roberts, Julia Sutton, Cedrick Ndhumba Shili, Dingbo Lin, Adel Pezeshki. Dietary Tryptophan Supplementation Alters Fat and Glucose Metabolism in a Low-Birthweight Piglet Model. Nutrients. 2021 Jul; 13(8):. doi: 10.3390/nu13082561. [PMID: 34444719]
Joseph Miller, Stacey House, Luis Lovato, Andrew Meltzer, Barry Hahn, Jahn Avarello, Terry Plasse, Ira Kalfus, Reza Fathi, Robert Silverman. Absence of QT prolongation after administration of a 24-mg bimodal-release ondansetron pill (RHB-102). The American journal of emergency medicine. 2021 05; 43(?):205-209. doi: 10.1016/j.ajem.2020.02.057. [PMID: 32139212]
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]
Manting D Chiang, Karen Frey, Chris Lee, Evan D Kharasch, Dani Tallchief, Christopher Sawyer, Jane Blood, Hyunmoon Back, Leonid Kagan, Simon Haroutounian. Plasma and cerebrospinal fluid pharmacokinetics of ondansetron in humans. British journal of clinical pharmacology. 2021 02; 87(2):516-526. doi: 10.1111/bcp.14412. [PMID: 32495990]
Amira M El-Kosasy, Lobna A Hussein, Nesma M Mohamed, Nahla N Salama. New and validated RP-HPLC Method for Quantification of Safinamide Mesylate in Presence of Its Basic Degradate, Levodopa and Ondansetron: Application to Human Plasma. Journal of chromatographic science. 2020 Sep; 58(9):789-795. doi: 10.1093/chromsci/bmaa043. [PMID: 32776090]
Manting Chiang, Hyun-Moon Back, Jong Bong Lee, Sarah Oh, Tiffany Guo, Simone Girgis, Celine Park, Simon Haroutounian, Leonid Kagan. Pharmacokinetic Modeling of the Impact of P-glycoprotein on Ondansetron Disposition in the Central Nervous System. Pharmaceutical research. 2020 Sep; 37(10):205. doi: 10.1007/s11095-020-02929-2. [PMID: 32989520]
Mohammad Reza Zirak, Gholamreza Karimi, Reza Rahimian, Amir Hossein Jafarian, A Wallace Hayes, Soghra Mehri. Tropisetron ameliorates cyclophosphamide-induced hemorrhagic cystitis in rats. European journal of pharmacology. 2020 Sep; 883(?):173310. doi: 10.1016/j.ejphar.2020.173310. [PMID: 32619674]
Jéssica Iara Gall, Amália Gonçalves Alves, Luiz Roberto Carraro Júnior, Taís da Silva Teixeira Rech, José Sebastião Dos Santos Neto, Diego Alves, Mayara Sandrielly Pereira Soares, Luiza Spohr, Rosélia Maria Spanevello, César Augusto Brüning, Cristiani Folharini Bortolatto. Insights into serotonergic and antioxidant mechanisms involved in antidepressant-like action of 2-phenyl-3-(phenylselanyl)benzofuran in mice. Progress in neuro-psychopharmacology & biological psychiatry. 2020 08; 102(?):109956. doi: 10.1016/j.pnpbp.2020.109956. [PMID: 32371105]
Cynthia Kwan, Dominique Bédard, Imane Frouni, Fleur Gaudette, Francis Beaudry, Adjia Hamadjida, Philippe Huot. Pharmacokinetic profile of the selective 5-HT3 receptor antagonist ondansetron in the rat: an original study and a minireview of the behavioural pharmacological literature in the rat. Canadian journal of physiology and pharmacology. 2020 Jul; 98(7):431-440. doi: 10.1139/cjpp-2019-0551. [PMID: 32017606]
Dandan Feng, Rui Jia, Zhengliang Ma, Xiaoping Gu. [Risk factors for nausea and vomiting after adolescent idiopathic scoliosis surgery]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2020 Mar; 40(3):394-399. doi: 10.12122/j.issn.1673-4254.2020.03.18. [PMID: 32376591]
Ramakant Gundu, Sanjay Pekamwar, Santosh Shelke, Santosh Shep, Deepak Kulkarni. Sustained release formulation of Ondansetron HCl using osmotic drug delivery approach. Drug development and industrial pharmacy. 2020 Mar; 46(3):343-355. doi: 10.1080/03639045.2020.1716372. [PMID: 31937128]
Bridget L Morse, Anil Kolur, Loyd R Hudson, Andrew T Hogan, Lisa Hong Chen, Ryan M Brackman, Geri A Sawada, John K Fallon, Philip C Smith, Kathleen M Hillgren. Pharmacokinetics of Organic Cation Transporter 1 (OCT1) Substrates in Oct1/2 Knockout Mice and Species Difference in Hepatic OCT1-Mediated Uptake. Drug metabolism and disposition: the biological fate of chemicals. 2020 02; 48(2):93-105. doi: 10.1124/dmd.119.088781. [PMID: 31771949]
Thi-Thao-Linh Nguyen, Van-An Duong, Han-Joo Maeng, Sang-Cheol Chi. Preparation of an oil suspension containing ondansetron hydrochloride as a sustained release parenteral formulation. Drug delivery and translational research. 2020 02; 10(1):282-295. doi: 10.1007/s13346-019-00687-2. [PMID: 31659599]
Yae Eun Chong, Manting Chiang, Kiran Deshpande, Simon Haroutounian, Leonid Kagan, Jong Bong Lee. Simultaneous quantification of ondansetron and tariquidar in rat and human plasma using a high performance liquid chromatography-ultraviolet method. Biomedical chromatography : BMC. 2019 Nov; 33(11):e4653. doi: 10.1002/bmc.4653. [PMID: 31322284]
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]
Fleur Gaudette, Dominique Bédard, Cynthia Kwan, Imane Frouni, Adjia Hamadjida, Francis Beaudry, Philippe Huot. Highly sensitive HPLC-MS/MS assay for the quantitation of ondansetron in rat plasma and rat brain tissue homogenate following administration of a very low subcutaneous dose. Journal of pharmaceutical and biomedical analysis. 2019 Oct; 175(?):112766. doi: 10.1016/j.jpba.2019.07.014. [PMID: 31330277]
Mingyu Duan, Li Qin, Dafang Zhong, Peng Zhang. Rapid structure identification of nineteen metabolites of ondansetron in human urine using LC/MSn. Biomedical chromatography : BMC. 2019 Oct; 33(10):e4618. doi: 10.1002/bmc.4618. [PMID: 31174234]
David Gunn, Klara Garsed, Ching Lam, Gulzar Singh, Melanie Lingaya, Verena Wahl, Beate Niesler, Amanda Henry, Ian P Hall, Peter Whorwell, Robin Spiller. Abnormalities of mucosal serotonin metabolism and 5-HT3 receptor subunit 3C polymorphism in irritable bowel syndrome with diarrhoea predict responsiveness to ondansetron. Alimentary pharmacology & therapeutics. 2019 09; 50(5):538-546. doi: 10.1111/apt.15420. [PMID: 31342534]
Mojtaba Shakibaie, Hamid Forootanfar, Atoosa Ghaseminejad, Azad Salimi, Atefeh Ameri, Mohsen Doostmohammadi, Elham Jafari, Hamid-Reza Rahimi. Ondansetron enhanced diclofenac-induced nephrotoxicity in mice. Journal of biochemical and molecular toxicology. 2019 Sep; 33(9):e22378. doi: 10.1002/jbt.22378. [PMID: 31332906]
Van-An Duong, Thi-Thao-Linh Nguyen, Han-Joo Maeng, Sang-Cheol Chi. Preparation of Ondansetron Hydrochloride-Loaded Nanostructured Lipid Carriers Using Solvent Injection Method for Enhancement of Pharmacokinetic Properties. Pharmaceutical research. 2019 Jul; 36(10):138. doi: 10.1007/s11095-019-2672-x. [PMID: 31350675]
Wei Zheng, Dong-Bin Cai, Qing-E Zhang, Jie He, Li-Yun Zhong, Kang Sim, Gabor S Ungvari, Yu-Ping Ning, Yu-Tao Xiang. Adjunctive ondansetron for schizophrenia: A systematic review and meta-analysis of randomized controlled trials. Journal of psychiatric research. 2019 06; 113(?):27-33. doi: 10.1016/j.jpsychires.2019.02.024. [PMID: 30878789]
Seyed Mostafa Mirakbari, Mohammad Hadi Shirazi. Poisoning with Tasty and Sweet Seed Pods of Bird of Paradise Plant Caesalpinia gilliessii. Wilderness & environmental medicine. 2019 Mar; 30(1):99-100. doi: 10.1016/j.wem.2018.09.001. [PMID: 30528075]
Mingyu Duan, Qi Zhao, Dafang Zhong, Yue Yuan. Pharmacokinetics of R-(-)ondansetron compared with that of S-(-)ondansetron in rats using an LC-MS/MS method. Biomedical chromatography : BMC. 2019 Mar; 33(3):e4426. doi: 10.1002/bmc.4426. [PMID: 30408206]
Scott Hartman, Elizabeth Brown, Elizabeth Loomis, Holly Ann Russell. Gastroenteritis in Children. American family physician. 2019 02; 99(3):159-165. doi: NULL. [PMID: 30702253]
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Peng Zhu, Zhi Ye, Dong Guo, Zongping Xiong, Shiqiong Huang, Jun Guo, Wei Zhang, James E Polli, Honghao Zhou, Qing Li, Yan Shu. Irinotecan Alters the Disposition of Morphine Via Inhibition of Organic Cation Transporter 1 (OCT1) and 2 (OCT2). Pharmaceutical research. 2018 Oct; 35(12):243. doi: 10.1007/s11095-018-2526-y. [PMID: 30361780]
Mingyu Duan, Li Qin, Dafang Zhong, Peng Zhang. Identification of novel ondansetron metabolites using LC/MSn and NMR. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Sep; 1095(?):138-141. doi: 10.1016/j.jchromb.2018.07.013. [PMID: 30077093]
Cunying Huang, Huihui Wan, Jing Zhang, Hongmin Zhong, Juan Li, YuMing Sun, Qing Wang, Hua Zhang. Quantification of ondansetron, granisetron and tropisetron in goat plasma using hydrophilic interaction liquid chromatography-solid phase extraction coupled with hydrophilic interaction liquid chromatography-triple quadrupole tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Sep; 1095(?):50-58. doi: 10.1016/j.jchromb.2018.07.009. [PMID: 30053687]
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