Rosoxacin: Difference between revisions

{{Short description|Antibiotic}}

{{more citations needed|date=August 2014}}

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 386256471

| image = Rosoxacin.svg

<!--Clinical data-->

| tradename = Eradacil

| Drugs.com = {{drugs.com|international|rosoxacin}}

| pregnancy_AU =

| pregnancy_US =

| legal_UK =

| legal_US =

| routes_of_administration =

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| elimination_half-life =

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<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 40034-42-2

| ATC_prefix = J01

| ATC_suffix = MB01

| PubChem = 287180

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB00817

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 253208

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 3Y1OT3J4NW

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D02305

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 131715

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 291157

<!--Chemical data-->

| melting_point = 290

| smiles = CCn1cc(C(=O)O)c(=O)c2ccc(-c3ccncc3)cc21

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XBPZXDSZHPDXQU-UHFFFAOYSA-N

'''Rosoxacin''' (also known as acrosoxacin, tradename Eradacil) is a [[quinolone antibiotic]] indicated for the treatment of urinary tract infections and certain [[sexually transmitted disease]]s. Rosoxacin is not available in the United States.

It was developed in 1978 by George Lesher and his colleagues at [[Sterling Drug|Winthrop-Stearns]] (now part of [[Sanofi-Aventis|sanofi-aventis]]), as an extension of the work that originally led to [[nalidixic acid]].<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>

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>

==Synthesis==

[[File:Rosoxacin synthesis.svg|thumb|center|700px|Rosoxacin synthesis:<ref>{{cite patent | inventor = Lescher Y, Carabateas PM | country = US | number = 3907808 | url = https://patents.google.com/patent/US3907808 | gdate = 23 September 1975 | title = 1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives | assign1 = STWB Inc. }}; Chem. Abstr., 84, 43880p (1975).</ref>]]

The synthesis of rosoxacin begins with a modified [[Hantzsch pyridine synthesis]] employing as component parts [[ammonium acetate]], two equivalents of [[methyl propiolate]], and one of [[3-nitrobenzaldehyde]]. 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 [[Gould-Jacobs reaction]] with methoxymethylenemalonate ester to form the 4-hydroxyquinoline ring, and then alkylation with [[ethyl iodide]] and saponification of the ester to complete the synthesis of the antibacterial agent rosoxacin ('''4''').

== See also ==

* [[Fluoroquinolone]]

== References ==

[[Category:4-Pyridyl compounds]]

[[Category:Carboxylic acids]]

{{antibiotic-stub}}