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{{Short description|Antibiotic}} |
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{{Drugbox| verifiedrevid = 295331117 |
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{{more citations needed|date=August 2014}} |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 386256471 |
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| IUPAC_name = 1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid |
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| IUPAC_name = 1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid |
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| image=Rosoxacin.png |
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| image = Rosoxacin.svg |
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<!--Clinical data--> |
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| CASNo_Ref = {{cascite}} |
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| tradename = Eradacil |
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| CAS_number=40034-42-2 |
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| Drugs.com = {{drugs.com|international|rosoxacin}} |
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| ATC_prefix=J01 |
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| pregnancy_AU = |
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| ATC_suffix=MB01 |
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| pregnancy_US = |
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| ATC_supplemental= |
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| legal_UK = |
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| PubChem=287180 |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 40034-42-2 |
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| ATC_prefix = J01 |
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| ATC_suffix = MB01 |
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| PubChem = 287180 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB00817 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 253208 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 3Y1OT3J4NW |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D02305 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 131715 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 291157 |
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<!--Chemical data--> |
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| C=17 | H=14 | N=2 | O=3 |
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| C=17 | H=14 | N=2 | O=3 |
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| melting_point = 290 |
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| molecular_weight = 294.30 g/mol |
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| smiles = CCn1cc(C(=O)O)c(=O)c2ccc(-c3ccncc3)cc21 |
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| bioavailability = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| metabolism = |
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| StdInChI = 1S/C17H14N2O3/c1-2-19-10-14(17(21)22)16(20)13-4-3-12(9-15(13)19)11-5-7-18-8-6-11/h3-10H,2H2,1H3,(H,21,22) |
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| protein_bound = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| elimination_half-life = |
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| StdInChIKey = XBPZXDSZHPDXQU-UHFFFAOYSA-N |
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| excretion = |
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| pregnancy_AU = |
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| pregnancy_US = |
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| legal_US = |
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| legal_UK = |
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}} |
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}} |
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'''Rosoxacin''' (also known as acrosoxacin, tradename Eradacil) is a quinolone antibiotic indicated for the treatment of urinary tract infections and certain sexually transmitted diseases. Rosoxacin is not available in the United States. |
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'''Rosoxacin''' (also known as acrosoxacin, tradename Eradacil) is a ] indicated for the treatment of urinary tract infections and certain ]s. Rosoxacin is not available in the United States. |
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It was developed in 1978 by George Lesher and his colleagues at ] (now part of ]), as an extension of the work that originally led to ].<ref>{{cite journal | vauthors = Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, Singh B, Thielking WH, Williams GL, Lesher GY |display-authors=6 |title=1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. I. Synthesis of 3- and 4-(3-aminophenyl)pyridine intermediates |journal=Journal of Heterocyclic Chemistry |date=1984 |volume=21 |issue=6 |pages=1849–1856 |doi=10.1002/jhet.5570210654}}</ref><ref>{{cite journal | vauthors = Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, Singh B, Thielking WH, Williams GL, Lesher GY |display-authors=6 |title=1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. II. Synthesis |journal=Journal of Heterocyclic Chemistry |date=1984 |volume=21 |issue=6 |pages=1857–1863 |doi=10.1002/jhet.5570210655}}</ref> |
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It was developed by Sanofi-Synthelabo (now part of ]). |
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It is classified as first generation.<ref name="pmid2173670">{{cite journal |author=Przybilla B, Georgii A, Bergner T, Ring J |title=Demonstration of quinolone phototoxicity in vitro |journal=Dermatologica |volume=181 |issue=2 |pages=98–103 |year=1990 |pmid=2173670 |doi= 10.1159/000247894|url=}}</ref> |
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It is classified as a first generation quinolone.<ref name="pmid2173670">{{cite journal | vauthors = Przybilla B, Georgii A, Bergner T, Ring J | title = Demonstration of quinolone phototoxicity in vitro | journal = Dermatologica | volume = 181 | issue = 2 | pages = 98–103 | year = 1990 | pmid = 2173670 | doi = 10.1159/000247894 }}</ref> |
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==See also== |
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==Synthesis== |
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The synthesis of rosoxacin begins with a modified ] employing as component parts ], two equivalents of ], and one of ]. Oxidation of the resulting dihydropyridine ('''2''') with nitric acid followed by saponification, decarboxylation, and reduction of the nitro group with iron and HCl acid gives aniline '''3'''. This undergoes the classic sequence of ] with methoxymethylenemalonate ester to form the 4-hydroxyquinoline ring, and then alkylation with ] and saponification of the ester to complete the synthesis of the antibacterial agent rosoxacin ('''4'''). |
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==References== |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{QuinoloneAntiBiotics}} |
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{{QuinoloneAntiBiotics}} |
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{{antibiotic-stub}} |
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{{antibiotic-stub}} |