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Revision as of 13:33, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456637530 of page Nalidixic_acid for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 03:40, 9 December 2024 edit Doremo (talk | contribs)Autopatrolled, Extended confirmed users124,004 edits consistent spelling 
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{{short description|First of the synthetic quinolone antibiotics}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Infobox drug
{{Drugbox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 394787048 | verifiedrevid = 462258277
| IUPAC_name = 1-ethyl-7-methyl-4-oxo-naphthyridine-3-carboxylic acid | IUPAC_name = 1-Ethyl-7-methyl-4-oxo-naphthyridine-3-carboxylic acid
| image = Nalidixic acid.png | image = Nalidixic Acid Structure.svg

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = NegGram, Wintomylon, others
| Drugs.com = {{drugs.com|CDI|nalidixic_acid}} | Drugs.com = {{drugs.com|CDI|nalidixic_acid}}
| pregnancy_US = B
| pregnancy_category = B <small>]</small>
| legal_US = Not FDA approved
| legal_status =
| routes_of_administration = Oral | routes_of_administration = Oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
Line 18: Line 16:
| metabolism = Partially Hepatic | metabolism = Partially Hepatic
| elimination_half-life = 6-7 hours, significantly longer in ] impairment | elimination_half-life = 6-7 hours, significantly longer in ] impairment

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 389-08-2 | CAS_number = 389-08-2
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3B91HWA56M | UNII = 3B91HWA56M
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00183 | KEGG = D00183
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 100147 | ChEBI = 100147
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 5 | ChEMBL = 5

<!--Chemical data--> <!--Chemical data-->
| C=12 | H=12 | N=2 | O=3 | C=12 | H=12 | N=2 | O=3
| molecular_weight = 232.235 g/mol
| 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MHWLWQUZZRMNGJ-UHFFFAOYSA-N | StdInChIKey = MHWLWQUZZRMNGJ-UHFFFAOYSA-N
}} }}

'''Nalidixic acid''' (tradenames '''Nevigramon''', '''NegGram''', '''Wintomylon''' and '''WIN 18,320''') is the first of the synthetic ]s.

In a technical sense, it is a naphthyridone, not a quinolone: its ring structure is a ] 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>

Synthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of ] 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.

Nalidixic acid is effective primarily against ], with minor anti-] activity. In lower concentrations, it acts in a ] 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.

It has historically been used for treating ], caused, for example, by '']'', '']'', '']'', '']'', and '']''. 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>

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 ] and ] 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.

== Adverse effects ==

Hives, rash, intense itching, or fainting soon after a dose may be a sign of ]. 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 ]s and ],<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 hemolytic anemia,<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 ] and young children, has been reported occasionally increased ].<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>

== Overdose ==

In case of overdose the patient experiences ], visual disturbances, balance disorders, ], metabolic acidosis and ].<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>

== Spectrum of bacterial susceptibility and resistance ==

'']'', '']'' and '']'' are generally susceptible to nalidixic acid, while other bacteria such as '']'', '']'', '']'' and '']'' 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>

== See also ==
*]
*]

== References ==
{{reflist|33em}}

== External links ==
* {{MedlinePlusDrugInfo|medmaster|a682042}}{{dead link|date=June 2012}}
* {{ 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 }}

{{QuinoloneAntiBiotics}}

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