, ▁but ▁only ▁in ▁a ▁limited ▁number ▁of ▁countries . ▁ ▁It ▁was ▁occasionally ▁used ▁in ▁France ▁( and ▁a ▁few ▁other ▁European ▁Count ries ) ▁to ▁treat ▁ur inary ▁tract ▁in fe ctions ▁under ▁the ▁trade ▁name ▁Ap ur one . ▁However ▁this ▁was ▁a ▁limited ▁indic ation ▁because ▁only ▁minimal ▁ser um ▁levels ▁were ▁achieved . ▁ ▁History ▁The ▁first ▁qu in ol one ▁used ▁was ▁n al id ix ic ▁acid ▁( was ▁market ed ▁in ▁many ▁countries ▁as ▁Neg ram ) ▁followed ▁by ▁the ▁flu oro quin ol one ▁fl um equ ine . ▁The ▁first - gener ation ▁flu oro quin ol one ▁agents , ▁such ▁as ▁fl um equ ine , ▁had ▁poor ▁distribution ▁into ▁the ▁body ▁t issues ▁and ▁limited ▁activity . ▁ ▁As ▁such ▁they ▁were ▁used ▁mainly ▁for ▁treatment ▁of ▁ur inary ▁tract ▁in fe ctions . ▁Fl um equ ine ▁( ben zo ▁qu in ol iz ine ) ▁was ▁first ▁pat ented ▁in ▁ 1 9 7 3 , ▁( G erman ▁Pat ent ) ▁by ▁R ik ker ▁L abs . ▁ ▁Fl um equ ine ▁is ▁a ▁known ▁ant im icro b ial ▁comp ound ▁described ▁and ▁claimed ▁in ▁U . S . ▁Pat . ▁No . ▁ 3 , 8 9 6 , 1 3 1 ▁( Example ▁ 3 ), ▁July ▁ 2 2 , ▁ 1 9 7 5 . ▁Fl um equ ine ▁is ▁the ▁first ▁qu in ol one ▁comp ound ▁with ▁a ▁flu or