Oxolinic acid

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Oxolinic acid
Oxolinic acid.png
Systematic (IUPAC) name
5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline- 7-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
?
Identifiers
CAS number 14698-29-4 YesY
ATC code J01MB05
PubChem CID 4628
ChemSpider 4467 N
UNII L0A22B22FT N
KEGG D02301 N
ChEBI CHEBI:138856 N
ChEMBL CHEMBL416755 N
Chemical data
Formula C13H11NO5 
Mol. mass 261.23 g/mol
 N (what is this?)  (verify)

Oxolinic acid is a quinolone antibiotic developed in Japan in the 1970s.[1][2] Dosages 12–20 mg/kg orally administered for five to ten days. The antibiotic works by inhibiting the enzyme DNA gyrase. It also acts as a dopamine reuptake inhibitor and has stimulant effects in mice.[3]

Synthesis[edit]

EMME (Ethoxy Methylene Malonic Diethyl Ester)

Oxolinic acid synthesis:[4]

See also[edit]

References[edit]

  1. ^ JP Patent 49138244
  2. ^ Gleckman R, Alvarez S, Joubert DW, Matthews SJ (August 1979). "Drug therapy reviews: oxolinic acid". American Journal of Hospital Pharmacy 36 (8): 1077–9. PMID 384788. 
  3. ^ Garcia de Mateos-Verchere J, Vaugeois JM, Naudin B, Costentin J (December 1998). "Behavioural and neurochemical evidence that the antimicrobial agent oxolinic acid is a dopamine uptake inhibitor". European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 8 (4): 255–9. doi:10.1016/S0924-977X(97)00083-7. PMID 9928913. 
  4. ^ Kaminsky, D.; Meltzer, R. I. (1968). "Quinoline antibacterial agents. Oxolinic acid and related compounds". Journal of Medicinal Chemistry 11 (1): 160–3. doi:10.1021/jm00307a041. PMID 5637164.  edit