Netilmicin (BioDeep_00000002097)

   

human metabolite blood metabolite Chemicals and Drugs Antibiotics


代谢物信息卡片


(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4-amino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl]oxy}-3-methyl-4-(methylamino)oxane-3,5-diol

化学式: C21H41N5O7 (475.30058360000004)
中文名称: 奈替米星
谱图信息: 最多检出来源 Homo sapiens(blood) 0.37%

分子结构信息

SMILES: CCNC1CC(C(C(C1OC2C(C(C(CO2)(C)O)NC)O)O)OC3C(CC=C(O3)CN)N)N
InChI: InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

描述信息

Netilmicin is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity. [PubChem] Netilmicin inhibits protein synthesis in susceptible organisms by binding to the bacterial 30S ribosomal subunit and interfering with mRNA binding and the acceptor tRNA site. The bactericidal effect of netilmiicin is not fully understood.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01G - Aminoglycoside antibacterials
S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives > S01AA - Antibiotics
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D005839 - Gentamicins
C784 - Protein Synthesis Inhibitor > C2363 - Aminoglycoside Antibiotic
D004791 - Enzyme Inhibitors > D011500 - Protein Synthesis Inhibitors
C254 - Anti-Infective Agent > C258 - Antibiotic

同义名列表

11 个代谢物同义名

(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4-amino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl]oxy}-3-methyl-4-(methylamino)oxane-3,5-diol; (1S,2S,3R,4S,6R)-4-amino-3-[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy]-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside; O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine; O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine; O-3-Deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine; 1-N-Ethylsisomicin; Netilmicin sulfate; NETILMICIN; Netilmycin; 4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside; Netilmicin



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)

3 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

  • Maritza Omaña-Molina, Virginia Vanzzini-Zago, Dolores Hernández-Martínez, María Reyes-Batlle, Ismael Castelan-Ramírez, Perla Hernández-Olmos, Lizbeth Salazar-Villatoro, Arturo González-Robles, Elizabeth Ramírez-Flores, Christopher Servín-Flores, Víctor Flores-Alvarado, Marino Alcántara-Castro, Jacob Lorenzo-Morales. Acanthamoeba keratitis in Mexico: Report of a clinical case and importance of sensitivity assays for a better outcome. Experimental parasitology. 2019 Jan; 196(?):22-27. doi: 10.1016/j.exppara.2018.11.005. [PMID: 30472333]
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  • Seema Mittal, Madhu Sharma, Uma Chaudhary. Fosfomycin use in multi drug resistant uropathogenic Escherichia coli. Infectious disorders drug targets. 2015; 15(3):196-201. doi: 10.2174/1871526515666150916141907. [PMID: 26374327]
  • Neda Soleimani, Mahdi Aganj, Liaqat Ali, Leili Shokoohizadeh, Türkân Sakinc. Frequency distribution of genes encoding aminoglycoside modifying enzymes in uropathogenic E. coli isolated from Iranian hospital. BMC research notes. 2014 Nov; 7(?):842. doi: 10.1186/1756-0500-7-842. [PMID: 25424607]
  • Gonca Sandal, Şenay Akbay, Metehan Ozen. Acquired Bartter-like syndrome association with netilmicin therapy in an extremely low birth weight infant. Renal failure. 2014 Feb; 36(1):123-5. doi: 10.3109/0886022x.2013.832861. [PMID: 24059693]
  • Kirtimaan Syal, Anand Srinivasan, Dibyajyoti Banerjee. Streptomycin interference in Jaffe reaction - possible false positive creatinine estimation in excessive dose exposure. Clinical biochemistry. 2013 Jan; 46(1-2):177-9. doi: 10.1016/j.clinbiochem.2012.10.031. [PMID: 23123914]
  • Stavros Lalas, Olga Gortzi, Vasilios Athanasiadis, John Tsaknis, Ioanna Chinou. Determination of antimicrobial activity and resistance to oxidation of moringa peregrina seed oil. Molecules (Basel, Switzerland). 2012 Feb; 17(3):2330-4. doi: 10.3390/molecules17032330. [PMID: 22367027]
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  • Chengwei Liu, Qin Xu, Dan Zhang, Xin Lu, Shulin Zhao. [Determination of netilmicin in rat serum using high performance liquid chromatography and resonance Rayleigh scattering]. Se pu = Chinese journal of chromatography. 2011 Feb; 29(2):157-61. doi: 10.3724/sp.j.1123.2011.00157. [PMID: 21598517]
  • Olayinka Aiyegoro, Adekanmi Adewusi, Sunday Oyedemi, David Akinpelu, Anthony Okoh. Interactions of antibiotics and methanolic crude extracts of Afzelia Africana (Smith.) against drug resistance bacterial isolates. International journal of molecular sciences. 2011; 12(7):4477-503. doi: 10.3390/ijms12074477. [PMID: 21845091]
  • Pritesh Devbhuti, Debasis Sikdar, Achintya Saha, Chandana Sengupta. Protective effect of ascorbic acid on netilmicin-induced lipid profile and peroxidation parameters in rabbit blood plasma. Acta poloniae pharmaceutica. 2011 Jan; 68(1):15-22. doi: NULL. [PMID: 21485697]
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  • Xiaojuan Chang, Jingdong Peng, Shaopu Liu, Limin Liu, Yongkuang Dai. [Determination of netilmicin in rat plasma by reversed-phase high performance liquid chromatography with fluorescence detection and pre-column derivatization]. Se pu = Chinese journal of chromatography. 2009 Nov; 27(6):794-8. doi: NULL. [PMID: 20352933]
  • Magdalena Rutkowska, Ewa Kamińska, Andrzej Piekarczyk, Katarzyna Nowicka, Krystyna Polak, Ewa Nowakowska-Szyrwińska, Katarzyna Szamotulska. [Optimalisation of netilmicin dosage based on therapeutic drug monitoring during the first days of life in very preterm neonates (gestational age 23-32 weeks)]. Medycyna wieku rozwojowego. 2009 Oct; 13(4):252-9. doi: . [PMID: 20081273]
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  • Delia Muntean, Monica Licker, Delia Berceanu-Văduva, Mihaela Crăciunescu, Elena Hogea, Mihaela Popa, Marcela Adămut, Matilda Rădulescu, Roxana Moldovan. [Aminoglycoside resistance of enterobacteria isolated from urinary infections in surgical departments]. Bacteriologia, virusologia, parazitologia, epidemiologia (Bucharest, Romania : 1990). 2008 Apr; 53(2):99-102. doi: NULL. [PMID: 19856848]
  • François Bouissou, Caroline Munzer, Stéphane Decramer, Bernard Roussel, Robert Novo, Denis Morin, Marie Pierre Lavocat, Claude Guyot, Sophie Taque, Michel Fischbach, Eric Ouhayoun, Chantal Loirat. Prospective, randomized trial comparing short and long intravenous antibiotic treatment of acute pyelonephritis in children: dimercaptosuccinic acid scintigraphic evaluation at 9 months. Pediatrics. 2008 Mar; 121(3):e553-60. doi: 10.1542/peds.2006-3632. [PMID: 18267977]
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  • Jens Rengelshausen, Bernd Beedgen, Konstantina Tsamouranis, Gerd Mikus, Ingeborg Walter-Sack, Walter E Haefeli, Otwin Linderkamp. Pharmacokinetics of a netilmicin loading dose on the first postnatal day in preterm neonates with very low gestational age. European journal of clinical pharmacology. 2006 Sep; 62(9):773-7. doi: 10.1007/s00228-006-0153-8. [PMID: 16865390]
  • Nan Sun, Weimin Mo, Baoxiang Hu, Zhenlu Shen. Adsorptive stripping voltammetric determination of netilmicin in the presence of formaldehyde. Analytical and bioanalytical chemistry. 2006 May; 385(1):161-7. doi: 10.1007/s00216-006-0383-8. [PMID: 16604342]
  • Sing Leung Lui, Suk Wai Cheng, Flora Ng, Suk Yi Ng, Kit Mui Wan, Terence Yip, Kai Chung Tse, Man Fai Lam, Kar Neng Lai, Wai Kei Lo. Cefazolin plus netilmicin versus cefazolin plus ceftazidime for treating CAPD peritonitis: effect on residual renal function. Kidney international. 2005 Nov; 68(5):2375-80. doi: 10.1111/j.1523-1755.2005.00700.x. [PMID: 16221243]
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  • J E East, J E Foweraker, F D Murgatroyd. Gentamicin induced ototoxicity during treatment of enterococcal endocarditis: resolution with substitution by netilmicin. Heart (British Cardiac Society). 2005 May; 91(5):e32. doi: 10.1136/hrt.2003.028308. [PMID: 15831617]
  • Susan Hemsworth, Anthony J Nunn, Karen Selwood, Caroline Osborne, Ashley Jones, Barry Pizer. Once-daily netilmicin for neutropenic pyrexia in paediatric oncology. Acta paediatrica (Oslo, Norway : 1992). 2005 Mar; 94(3):268-74. doi: 10.1111/j.1651-2227.2005.tb03068.x. [PMID: 16028643]
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  • Eivind Witsø, Leif Persen, Pål Benum, Arild Aamodt, Otto Schnell Husby, Kåre Bergh. High local concentrations without systemic adverse effects after impaction of netilmicin-impregnated bone. Acta orthopaedica Scandinavica. 2004 Jun; 75(3):339-46. doi: 10.1080/00016470410001295. [PMID: 15260428]
  • Claus Klingenberg, Lars Småbrekke, Tore Lier, Trond Flaegstad. Validation of a simplified netilmicin dosage regimen in infants. Scandinavian journal of infectious diseases. 2004; 36(6-7):474-9. doi: 10.1080/00365540410020613. [PMID: 15307571]
  • Andrzej Piekarczyk, Ewa Kaminska, Witold Taljanski, Krystyna Sosonowska, Beata Poszwinska, Magdalena Rutkowska. [Pharmacokinetics of netilmicin in neonates]. Medycyna wieku rozwojowego. 2003 Oct; 7(4 Pt 2):547-55. doi: NULL. [PMID: 15213369]
  • Nerea Jauregizar, Jeff A Wald, Ander Astobieta, Jose M Rodriguez Sasiain, John C Lukas, Rosario Calvo. Population pharmacokinetics of netilmicin in short-term prophylactic treatment. British journal of clinical pharmacology. 2003 Jun; 55(6):552-9. doi: 10.1046/j.1365-2125.2003.01783.x. [PMID: 12814449]
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  • Aránzazu Zarzuelo, Amparo Sánchez-Navarro, Francisco G López, José M Lanao. Influence of dose on the disposition kinetics of netilmicin in the isolated kidney of the rat. European journal of drug metabolism and pharmacokinetics. 2002 Apr; 27(2):127-33. doi: 10.1007/bf03190427. [PMID: 12064371]
  • Eivind Witsø, Leif Persen, Pål Benum, Kåre Bergh. Release of netilmicin and vancomycin from cancellous bone. Acta orthopaedica Scandinavica. 2002 Apr; 73(2):199-205. doi: 10.1080/000164702753671812 . [PMID: 12079020]
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