Oxamniquine (BioDeep_00000003330)

 

Secondary id: BioDeep_00000397934

human metabolite blood metabolite


代谢物信息卡片


(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol

化学式: C14H21N3O3 (279.1582836)
中文名称: 硝羟四氢喹啉胺
谱图信息: 最多检出来源 Homo sapiens(blood) 59.44%

分子结构信息

SMILES: CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
InChI: InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3

描述信息

An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)
P - Antiparasitic products, insecticides and repellents > P02 - Anthelmintics > P02B - Antitrematodals > P02BA - Quinoline derivatives and related substances
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent

同义名列表

5 个代谢物同义名

(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol; Oxaminiquine; oxamniquine; Vansil; Mansil



数据库引用编号

20 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

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

  • Valentin Buchter, Yih Ching Ong, François Mouvet, Abdallah Ladaycia, Elise Lepeltier, Ursula Rothlisberger, Jennifer Keiser, Gilles Gasser. Multidisciplinary Preclinical Investigations on Three Oxamniquine Analogues as New Drug Candidates for Schistosomiasis*. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Nov; 26(66):15232-15241. doi: 10.1002/chem.202002856. [PMID: 32852116]
  • 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]
  • Sören Frahm, Anisuzzaman Anisuzzaman, Ulrich Fabien Prodjinotho, Nermina Vejzagić, Admar Verschoor, Clarissa Prazeres da Costa. A novel cell-free method to culture Schistosoma mansoni from cercariae to juvenile worm stages for in vitro drug testing. PLoS neglected tropical diseases. 2019 01; 13(1):e0006590. doi: 10.1371/journal.pntd.0006590. [PMID: 30689639]
  • Rebecca Nespoli Lima, Paulo Marcos Zech Coelho, Ana Carolina A Mattos, Clélia Christina Mello Silva, Ronaldo de Carvalho Augusto, Ester Maria Mota, Samaly de Souza, Georgia Correa Atella, Suellen Silva Cabral, George Eduardo Gabriel Kluck, Marta Julia Faro. Combined treatment of Biomphalaria glabrata infected by Schistosoma mansoni with oxamniquine and praziquantel: Reproductive histological and metabolic aspects. Experimental parasitology. 2017 Dec; 183(?):6-12. doi: 10.1016/j.exppara.2017.10.001. [PMID: 29017937]
  • Frédéric D Chevalier, Winka Le Clec'h, Nina Eng, Anastasia R Rugel, Rafael Ramiro de Assis, Guilherme Oliveira, Stephen P Holloway, Xiaohang Cao, P John Hart, Philip T LoVerde, Timothy J C Anderson. Independent origins of loss-of-function mutations conferring oxamniquine resistance in a Brazilian schistosome population. International journal for parasitology. 2016 06; 46(7):417-24. doi: 10.1016/j.ijpara.2016.03.006. [PMID: 27073078]
  • Anthony Danso-Appiah, Piero L Olliaro, Sarah Donegan, David Sinclair, Jürg Utzinger. Drugs for treating Schistosoma mansoni infection. The Cochrane database of systematic reviews. 2013 Feb; ?(2):CD000528. doi: 10.1002/14651858.cd000528.pub2. [PMID: 23450530]
  • N El-Enany, F Belal, M Rizk. Spectrofluorimetric determination of oxamniquine in dosage forms and spiked human plasma through derivatization with 1-dimethylaminonaphthalene-5-sulphonyl chloride. Journal of fluorescence. 2008 Mar; 18(2):349-55. doi: 10.1007/s10895-007-0274-1. [PMID: 18058206]
  • Martin J Enk, Naftale Katz, Paulo Marcos Zech Coelho. A case of Schistosoma mansoni infection treated during the prepatent period. Nature clinical practice. Gastroenterology & hepatology. 2008 Feb; 5(2):112-5. doi: 10.1038/ncpgasthep1037. [PMID: 18253140]
  • Joelma R de Souza, Clarice N L Morais, Marcílio L Aroucha, Paulo J C Miranda, Constança S Barbosa, Ana Lúcia C Domingues, Luiz B Carvalho Júnior, Frederico G C Abath, Silvia M L Montenegro. Treatment of human acute schistosomiasis with oxamniquine induces an increase in interferon-gamma response to Schistosoma mansoni antigens. Memorias do Instituto Oswaldo Cruz. 2007 May; 102(2):225-8. doi: 10.1590/s0074-02762007005000002. [PMID: 17426890]
  • Telcia V B Magalhães, Giovanni Gazzinelli, Maria Carolina B Alvarez, F C Lima e Silva, Lucia Alves Oliveira Fraga, Alda Maria S Silveira, Andrea Gazzinelli, Jeffrey Bethony, Philip LoVerde, Iramaya R Caldas, Rodrigo Correa-Oliveira, Aluízio Prata. Comparative clinical and ultrasound study of egg-negative and egg-positive individuals from Schistosoma mansoni low morbidity endemic areas, and hospitalized patients with hepatosplenic disease. Revista da Sociedade Brasileira de Medicina Tropical. 2005 Jan; 38(1):33-7. doi: 10.1590/s0037-86822005000100007. [PMID: 15717092]
  • Martin J Enk, Amanda Amorim, Virginia T Schall. Acute schistosomiasis outbreak in the metropolitan area of Belo Horizonte, Minas Gerais: alert about the risk of unnoticed transmission increased by growing rural tourism. Memorias do Instituto Oswaldo Cruz. 2003 Sep; 98(6):745-50. doi: 10.1590/s0074-02762003000600006. [PMID: 14595449]
  • M L A Ferrari, P M Z Coelho, C M F Antunes, C A P Tavares, A S da Cunha. Efficacy of oxamniquine and praziquantel in the treatment of Schistosoma mansoni infection: a controlled trial. Bulletin of the World Health Organization. 2003; 81(3):190-6. doi: . [PMID: 12764515]
  • José Albino da Paz, Marcelo Valente, Erasmo Barbante Casella, Maria Joaquina Marques-Dias. Spinal cord schistosomiasis in children: analysis of seven cases. Arquivos de neuro-psiquiatria. 2002 Jun; 60(2-A):224-30. doi: 10.1590/s0004-282x2002000200007. [PMID: 12068349]
  • Patrícia Ivana Pires Bonesso-Sabadini, Luiz Cândido de Souza Dias. Altered response of strain of Schistosoma mansoni to oxamniquine and praziquantel. Memorias do Instituto Oswaldo Cruz. 2002 Apr; 97(3):381-5. doi: 10.1590/s0074-02762002000300019. [PMID: 12048569]
  • Yara M Gomes, Valéria R A Pereira, Mineo Nakazawa, Ulisses Montarroyos, Wayner V Souza, Frederico G C Abath. Antibody isotype responses to egg antigens in human chronic Schistosomiasis mansoni before and after treatment. Memorias do Instituto Oswaldo Cruz. 2002; 97 Suppl 1(?):111-2. doi: 10.1590/s0074-02762002000900022. [PMID: 12426604]
  • Horacio Manuel Santana Teles, Maria Esther de Carvalho, Cláudio Santos Ferreira, Fabiana Zacharias, Valquíria Rosa de Lima, Maria Lucia Condino Fadel. Schistosomiasis mansoni in Bananal (State of São Paulo, Brazil): I. Efficiency of diagnostic and treatment procedures. Memorias do Instituto Oswaldo Cruz. 2002; 97 Suppl 1(?):181-6. doi: 10.1590/s0074-02762002000900035. [PMID: 12426617]
  • K M Mahmoud, M A Sobh, A E El-Agroudy, F E Mostafa, M E Baz, A A Shokeir, M A Ghoneim. Impact of schistosomiasis on patient and graft outcome after renal transplantation: 10 years' follow-up. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2001 Nov; 16(11):2214-21. doi: 10.1093/ndt/16.11.2214. [PMID: 11682670]
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  • M Rizk, F Belal, F Ibrahim, S M Ahmed, N M El-Enany. A simple kinetic spectrophotometric method for the determination of oxamniquine in formulations and spiked biological fluids. Journal of pharmaceutical and biomedical analysis. 2000 Aug; 23(2-3):503-13. doi: 10.1016/s0731-7085(00)00320-4. [PMID: 10933544]
  • M Rizk, F Belal, F Ibrahim, S M Ahmed, N M el-Enany. Fluorimetric determination of oxamniquine in biological fluids. Farmaco (Societa chimica italiana : 1989). 1999 Jan; 54(1-2):47-50. doi: 10.1016/s0014-827x(98)00091-3. [PMID: 10321028]
  • P G Fallon, J S Mubarak, R E Fookes, M Niang, A E Butterworth, R F Sturrock, M J Doenhoff. Schistosoma mansoni: maturation rate and drug susceptibility of different geographic isolates. Experimental parasitology. 1997 May; 86(1):29-36. doi: 10.1006/expr.1997.4149. [PMID: 9149238]
  • F Frézard, A L de Melo. Evaluation of the schistosomicidal efficacy of liposome-entrapped oxamniquine. Revista do Instituto de Medicina Tropical de Sao Paulo. 1997 Mar; 39(2):97-100. doi: 10.1590/s0036-46651997000200006. [PMID: 9394522]
  • L M Silva, Z A Andrade. Immunostimulation as adjuvant for the chemotherapy of experimental schistosomiasis. Revista do Instituto de Medicina Tropical de Sao Paulo. 1997 Jan; 39(1):11-4. doi: 10.1590/s0036-46651997000100003. [PMID: 9394530]
  • N Araújo, C P de Souza, L K Passos, A J Simpson, E Dias Neto, T R Pereira, C Cerutti Júnior, F E de Alencar, R Dietze, N Katz. [Susceptibility to chemotherapeutic agents of Schistosoma mansoni isolates from patients treated with oxamniquine and praziquantel and not cured]. Revista da Sociedade Brasileira de Medicina Tropical. 1996 Sep; 29(5):467-76. doi: 10.1590/s0037-86821996000500010. [PMID: 8966311]
  • P G Fallon, R E Fookes, G A Wharton. Temporal differences in praziquantel- and oxamniquine-induced tegumental damage to adult Schistosoma mansoni: implications for drug-antibody synergy. Parasitology. 1996 Jan; 112 ( Pt 1)(?):47-58. doi: 10.1017/s0031182000065069. [PMID: 8587801]
  • G O Kokwaro, A A Indalo, G Taylor. Pharmacokinetics of oxamniquine in rabbit and rat. European journal of drug metabolism and pharmacokinetics. 1996 Jan; 21(1):13-6. doi: 10.1007/bf03190272. [PMID: 8839672]
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  • A F Badawi, H A Awney, M H Mostafa. Formation of promutagenic methylation damage in tissue-DNA of mice treated with antischistosomal agents. Cancer letters. 1993 Dec; 75(3):167-73. doi: 10.1016/0304-3835(93)90059-i. [PMID: 8313351]
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  • M M Ismail, A M Farghaly, M M Hassan, S M Youssef, F E Mohamed. Alternate chemotherapy in experimental schistosomiasis. Journal of the Egyptian Society of Parasitology. 1992 Aug; 22(2):321-6. doi: NULL. [PMID: 1500769]
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  • N Katz, R S Rocha, C P de Souza, P Coura Filho, J I Bruce, G C Coles, G K Kinoti. Efficacy of alternating therapy with oxamniquine and praziquantel to treat Schistosoma mansoni in children following failure of first treatment. The American journal of tropical medicine and hygiene. 1991 May; 44(5):509-12. doi: 10.4269/ajtmh.1991.44.509. [PMID: 1905880]
  • G O Kokwaro, G Taylor. Oxamniquine pharmacokinetics in healthy Kenyan African volunteers. East African medical journal. 1991 May; 68(5):359-64. doi: NULL. [PMID: 1935730]
  • N de Jonge, G Schommer, H Feldmeier, F W Krijger, A A Dafalla, U Bienzle, A M Deelder. Mixed Schistosoma haematobium and S. mansoni infection: effect of different treatments on the serum level of circulating anodic antigen (CAA). Acta tropica. 1990 Oct; 48(1):25-35. doi: 10.1016/0001-706x(90)90062-5. [PMID: 1980801]
  • G O Kokwaro, G Taylor. Partitioning of oxaminiquine into brain tissue following intravenous administration to female Wistar rats. Drug and chemical toxicology. 1990; 13(4):347-54. doi: 10.3109/01480549009032291. [PMID: 2279462]
  • A M Amin, E G Mikhail. Experimental schistosomiasis mansoni: electrophoretic studies on serum proteins before and after administration of oxamniquine. Journal of the Egyptian Society of Parasitology. 1989 Dec; 19(2):447-60. doi: . [PMID: 2504823]
  • J R Lambertucci, J Modha, M Doenhoff. Schistosoma mansoni: the therapeutic efficacy of oxamniquine is enhanced by immune serum. Transactions of the Royal Society of Tropical Medicine and Hygiene. 1989 May; 83(3):362-3. doi: 10.1016/0035-9203(89)90505-1. [PMID: 2515623]
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  • P Torres, R Franjola, J Pérez, S Auad, F Uherek, J C Miranda, L Flores, J Riquelme, S Salazar, C Hermosilla. [Epidemiology of diphyllobothriasis in the Valdivia river basin, Chile]. Revista de saude publica. 1989 Feb; 23(1):45-57. doi: 10.1590/s0034-89101989000100007. [PMID: 2814310]
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  • A M Amin, E G Mikhail. Susceptibility of Schistosoma mansoni prevalent in Saudi Arabia to oxamniquine in experimentally infected mice. The Journal of tropical medicine and hygiene. 1988 Aug; 91(4):192-5. doi: NULL. [PMID: 3136251]
  • I M Abdel Rahim, A A Haridi, A A Abdel-Hameed. Field study of different oxamniquine dose for Schistosoma mansoni in Gezira, Sudan. The Journal of tropical medicine and hygiene. 1988 Jun; 91(3):131-7. doi: NULL. [PMID: 3134556]
  • M A Sobh, F E Moustafa, S M Sally, A M Deelder, M A Ghoniem. Effect of anti-schistosomal treatment on schistosomal-specific nephropathy. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 1988; 3(6):744-51. doi: 10.1093/oxfordjournals.ndt.a091748. [PMID: 3147416]
  • A M Polderman, B Gryseels, P De Caluwe. Cure rates and egg reduction in treatment of intestinal schistosomiasis with oxamniquine and praziquantel in Maniema, Zaire. Transactions of the Royal Society of Tropical Medicine and Hygiene. 1988; 82(1):115-6. doi: 10.1016/0035-9203(88)90282-9. [PMID: 3140441]
  • M A Madwar, M M Hassan, G T Strickland. Circulating antigens for assessing cure in schistosomiasis mansoni. Transactions of the Royal Society of Tropical Medicine and Hygiene. 1988; 82(6):881-4. doi: 10.1016/0035-9203(88)90025-9. [PMID: 3151529]
  • B C Nascimento, M Chamone. The separation of complement inhibitors from patients with schistosomiasis or Chagas' disease by gel filtration on Sephadex G-200: a preliminary study. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 1988; 21(2):295-9. doi: NULL. [PMID: 3144403]
  • R Campos, P L Pinto, E J de Sant'Ana, A A Moreira, V Amato Neto. [Treatment of schistosomiasis mansoni with a combination of oxamniquine and praziquantel. I--Experimental observations related to the pre-patent phase]. Revista do Hospital das Clinicas. 1987 Sep; 42(5):201-3. doi: NULL. [PMID: 3135570]
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