Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Nalidixic acid: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 456637530 of page Nalidixic_acid for the Chem/Drugbox validation project (updated: 'DrugBank'). |
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{{short description|First of the synthetic quinolone antibiotics}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Nalidixic_acid|oldid=456637530}} 456637530] of page [[Nalidixic_acid]] with values updated to verified values.}} |
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{{Infobox drug |
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{{Drugbox |
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| |
| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 462258277 |
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| IUPAC_name = 1- |
| IUPAC_name = 1-Ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid |
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| image = Nalidixic |
| image = Nalidixic Acid Structure.svg |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = NegGram, Wintomylon, others |
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| Drugs.com = {{drugs.com|CDI|nalidixic_acid}} |
| Drugs.com = {{drugs.com|CDI|nalidixic_acid}} |
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| pregnancy_US = B |
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| pregnancy_category = B <small>[[U.S.]]</small> |
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| legal_US = Not FDA approved |
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| legal_status = |
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| routes_of_administration = Oral |
| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| metabolism = Partially Hepatic |
| metabolism = Partially Hepatic |
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| elimination_half-life = 6-7 hours, significantly longer in [[renal]] impairment |
| elimination_half-life = 6-7 hours, significantly longer in [[renal]] impairment |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 389-08-2 |
| CAS_number = 389-08-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3B91HWA56M |
| UNII = 3B91HWA56M |
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| KEGG_Ref = {{keggcite| |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00183 |
| KEGG = D00183 |
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| ChEBI_Ref = {{ebicite| |
| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 100147 |
| ChEBI = 100147 |
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| ChEMBL_Ref = {{ebicite| |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 5 |
| ChEMBL = 5 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=12 | H=12 | N=2 | O=3 |
| C=12 | H=12 | N=2 | O=3 |
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| molecular_weight = 232.235 g/mol |
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| smiles = O=C\2c1c(nc(cc1)C)N(/C=C/2C(=O)O)CC |
| smiles = O=C\2c1c(nc(cc1)C)N(/C=C/2C(=O)O)CC |
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| StdInChI_Ref = {{stdinchicite| |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17) |
| StdInChI = 1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17) |
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| StdInChIKey_Ref = {{stdinchicite| |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MHWLWQUZZRMNGJ-UHFFFAOYSA-N |
| StdInChIKey = MHWLWQUZZRMNGJ-UHFFFAOYSA-N |
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}} |
}} |
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'''Nalidixic acid''' (tradenames '''Nevigramon''', '''NegGram''', '''Wintomylon''' and '''WIN 18,320''') is the first of the synthetic [[quinolone antibiotic]]s. |
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In a technical sense, it is a naphthyridone, not a quinolone: its ring structure is a [[1,8-Naphthyridine|1,8-naphthyridine]] nucleus that contains two nitrogen atoms, unlike quinoline, which has a single nitrogen atom.<ref name=jac2003>{{cite journal | vauthors = Emmerson AM, Jones AM | title = The quinolones: decades of development and use | journal = The Journal of Antimicrobial Chemotherapy | volume = 51 | issue = Suppl 1 | pages = 13–20 | date = May 2003 | pmid = 12702699 | doi = 10.1093/jac/dkg208 | doi-access = free }}</ref> |
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Synthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of [[chloroquine]] manufacture in the 1960s;<ref>{{cite journal | vauthors = Lesher GY, Froelich EJ, Gruett MD, Bailey JH, Brundage RP | title = 1,8-Naphthyridine Derivatives. A New Class of Chemotherapeutic Agents | journal = Journal of Medicinal and Pharmaceutical Chemistry | volume = 5 | issue = 5 | pages = 1063–1065 | date = September 1962 | pmid = 14056431 | doi = 10.1021/jm01240a021 }}</ref> nalidixic acid itself was used clinically, starting in 1967. |
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Nalidixic acid is effective primarily against [[Gram-negative bacteria]], with minor anti-[[Gram-positive]] activity. In lower concentrations, it acts in a [[bacteriostatic]] manner; that is, it inhibits growth and reproduction. In higher concentrations, it is bactericidal, meaning that it kills bacteria instead of merely inhibiting their growth. |
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It has historically been used for treating [[urinary tract infections]], caused, for example, by ''[[Escherichia coli]]'', ''[[Proteus (bacterium)|Proteus]]'', ''[[Shigella]]'', ''[[Enterobacter]]'', and ''[[Klebsiella]]''. It is no longer clinically used for this indication in the US as less toxic and more effective agents are available. The marketing authorization for nalidixic acid has been suspended throughout the EU.<ref>{{Cite web|url=https://www.ema.europa.eu/en/medicines/human/referrals/quinolone-fluoroquinolone-containing-medicinal-products|title=Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics|date=11 March 2019|website=European Medicines Agency}}</ref> |
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It is also a tool in studies as a regulation of bacterial division. It selectively and reversibly blocks DNA replication in susceptible bacteria. Nalidixic acid and related antibiotics inhibit a subunit of [[DNA gyrase]] and [[topoisomerase IV]] and induce formation of cleavage complexes.<ref>{{cite journal | vauthors = Pommier Y, Leo E, Zhang H, Marchand C | title = DNA topoisomerases and their poisoning by anticancer and antibacterial drugs | journal = Chemistry & Biology | volume = 17 | issue = 5 | pages = 421–433 | date = May 2010 | pmid = 20534341 | pmc = 7316379 | doi = 10.1016/j.chembiol.2010.04.012 | doi-access = free }}</ref> It also inhibits the nicking-closing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA. |
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== Adverse effects == |
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Hives, rash, intense itching, or fainting soon after a dose may be a sign of [[anaphylaxis]]. Common adverse effects include rash, itchy skin, blurred or double vision, halos around lights, changes in color vision, nausea, vomiting, and diarrhea. Nalidixic acid may also cause [[convulsion]]s and [[hyperglycemia]],<ref>{{cite journal | vauthors = Fraser AG, Harrower AD | title = Convulsions and hyperglycaemia associated with nalidixic acid | journal = British Medical Journal | volume = 2 | issue = 6101 | pages = 1518 | date = December 1977 | pmid = 589309 | pmc = 1632822 | doi = 10.1136/bmj.2.6101.1518 }}</ref> photosensitivity reactions,<ref name="pmid4733958">{{cite journal | vauthors = Ramsay CA | title = Photosensitivity from nalidixic acid | journal = Proceedings of the Royal Society of Medicine | volume = 66 | issue = 8 | pages = 747 | date = August 1973 | pmid = 4733958 | pmc = 1645105 | doi = 10.1177/003591577306600805 }}</ref> and sometimes haemolytic anaemia,<ref name="pmid4653901">{{cite journal | vauthors = Gilbertson C, Jones DR | title = Haemolytic anaemia with nalidixic acid | journal = British Medical Journal | volume = 4 | issue = 5838 | pages = 493 | date = November 1972 | pmid = 4653901 | pmc = 1786728 | doi = 10.1136/bmj.4.5838.493-a }}</ref><ref name="pmid6811074">{{cite journal | vauthors = Tafani O, Mazzoli M, Landini G, Alterini B | title = Fatal acute immune haemolytic anaemia caused by nalidixic acid | journal = British Medical Journal | volume = 285 | issue = 6346 | pages = 936–937 | date = October 1982 | pmid = 6811074 | pmc = 1499997 | doi = 10.1136/bmj.285.6346.936-a }}</ref> thrombocytopenia<ref name="pmid6435742">{{cite journal | vauthors = Meyboom RH | title = Thrombocytopenia induced by nalidixic acid | journal = British Medical Journal | volume = 289 | issue = 6450 | pages = 962 | date = October 1984 | pmid = 6435742 | pmc = 1443179 | doi = 10.1136/bmj.289.6450.962 }}</ref> or leukopenia. Particularly in [[infants]] and young children, has been reported occasionally increased [[intracranial pressure]].<ref name="pmid6025983">{{cite journal | vauthors = Boréus LO, Sundström B | title = Intracranial hypertension in a child during treatment with nalidixic acid | journal = British Medical Journal | volume = 2 | issue = 5554 | pages = 744–745 | date = June 1967 | pmid = 6025983 | pmc = 1841777 | doi = 10.1136/bmj.2.5554.744 }}</ref><ref name="pmid6055749">{{cite journal | vauthors = Kremer L, Walton M, Wardle EN | title = Nalidixic acid and intracranial hypertension | journal = British Medical Journal | volume = 4 | issue = 5577 | pages = 488 | date = November 1967 | pmid = 6055749 | pmc = 1748506 | doi = 10.1136/bmj.4.5577.488-a }}</ref><ref name="pmid4419059">{{cite journal | vauthors = Deonna T, Guignard JP | title = Acute intracranial hypertension after nalidixic acid administration | journal = Archives of Disease in Childhood | volume = 49 | issue = 9 | pages = 743 | date = September 1974 | pmid = 4419059 | pmc = 1649016 | doi = 10.1136/adc.49.9.743 }}</ref> |
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== Overdose == |
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In case of overdose the patient experiences [[headache]], visual disturbances, balance disorders, [[mental confusion]], metabolic acidosis and [[seizures]].<ref name="pmid17175866">{{cite journal | vauthors = Eizadi-Mood N | title = Nalidixic acid overdose and metabolic acidosis | journal = CJEM | volume = 8 | issue = 2 | pages = 78 | date = March 2006 | pmid = 17175866 | doi = 10.1017/s148180350001349x | doi-access = free }}</ref> |
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== Spectrum of bacterial susceptibility and resistance == |
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''[[Aeromonas hydrophila]]'', ''[[Clostridium]]'' and ''[[Haemophilus]]'' are generally susceptible to nalidixic acid, while other bacteria such as ''[[Bifidobacteria]]'', ''[[Lactobacillus]]'', ''[[Pseudomonas]]'' and ''[[Staphylococcus]]'' are resistant.<ref>{{ cite web | title = Nalidixic acid spectrum of bacterial susceptibility and Resistance | url = http://www.toku-e.com/Upload/Products/PDS/20120522005430.pdf | publisher = Toku-E | date = 2011-09-14 | access-date = 2012-05-14 | archive-url = https://web.archive.org/web/20160110130057/http://www.toku-e.com/Upload/Products/PDS/20120522005430.pdf | archive-date = 2016-01-10 | url-status = dead }}</ref> ''Salmonella enterica'' serovar Typhimurium strain ATCC14028 acquires nalidixic acid resistance when ''gyrB'' gene is mutated (strain IR715).<ref name="pmid7868611">{{cite journal | vauthors = Stojiljkovic I, Bäumler AJ, Heffron F | title = Ethanolamine utilization in Salmonella typhimurium: nucleotide sequence, protein expression, and mutational analysis of the cchA cchB eutE eutJ eutG eutH gene cluster | journal = Journal of Bacteriology | volume = 177 | issue = 5 | pages = 1357–66 | date = March 1995 | pmid = 7868611 | pmc = 176743 | doi = 10.1128/jb.177.5.1357-1366.1995 }}</ref> |
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== See also == |
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*[[Amfonelic acid]] |
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*[[Oxolinic acid]] |
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== References == |
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{{reflist|33em}} |
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== External links == |
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* {{MedlinePlusDrugInfo|medmaster|a682042}}{{dead link|date=June 2012}} |
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* {{ cite web | url = http://www.healthdigest.org/topics/category/1464-nalidixic-acid-dosage-interactions-side-effects-how-to-use | publisher = HealthDigest.org | title = Nalidixic acid }} |
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{{QuinoloneAntiBiotics}} |
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{{Authority control}} |
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[[Category:Quinolone antibiotics]] |
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[[Category:Naphthyridines]] |
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[[Category:WIN compounds]] |
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[[Category:Carboxylic acids]] |
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[[Category:Topoisomerase inhibitors]] |