5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

• ChemBase ID: 104463
• Molecular Formular: C13H11NO5
• Molecular Mass: 261.23014
• Monoisotopic Mass: 261.06372246
• SMILES: CCn1cc(C(=O)O)c(=O)c2cc3c(OCO3)cc12
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc1OCOc1c2
• InChI: InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
• InChIKey: KYGZCKSPAKDVKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• IUPAC Traditional name: ossian; 5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• Synonyms: 5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid; 5,8-Dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid; Oxolinic acid; OXOLINIC ACID; Utibid; Prodoxol; Starner; 5-Ethyl-5,8-dihydro-8-oxo-1,3-Dioxolo[4,5-g]quinoline-7-carboxylic Acid; 1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic Acid; NSC 110364; Nidantin; Ossian; Oxoboi; Pietil; Prodoxal; Uritrate; Urotrate; W 4565

Database IDs

• CAS Number: 14698-29-4
• EC Number: 238-750-8
• MDL Number: MFCD00056775
• Beilstein Number: 620635
• PubChem SID: 24278604; 162092766
• PubChem CID: 4628

CALCULATED PROPERTIES

• Acid pKa: 5.579866
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0903233
• LogD (pH = 7.4): -0.46510977
• Log P: 1.3531469
• Molar Refractivity: 65.8433 cm^3
• Polarizability: 24.676064 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.5 M NaOH: soluble50 mg/mL, clear, very faintly yellow; Aqueous Base
• Apperance: White Solid
• Melting Point: >260°C (dec.)

Safety Information

• Storage Condition: 2-8°C, Desiccate; Refrigerator
• RTECS: JI5075000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 22-24/25; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: DNA-gyrase inhibitor; Reported to reduce brain HIAA levels in rats; Reported to reduce brain serotonin levels in rats

Product Information

• Purity: ≥97.0% (T); 95+%
• Suitability: suitable for 1694 per US EPA
• Application(s): Antibacterial agent effective against Proteus; Antibiotic
• Empirical Formula (Hill Notation): C13H11NO5

DETAILS

Sigma Aldrich - O0877

Application
Oxolinic acid is a quinolone antibiotic used for studies on DNA winding and coiling and for studies on dopaminergic neurotransmission processes. It is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia coli and Salmonella enterica. It is added to culture medium for the isolation of Gardnerella vaginalis1.
Biochem/physiol Actions
Oxolinic acid is a DNA-gyrase (topoisomerase II) inhibitor used for studies on DNA winding and coiling. Acts as a dopamine reuptake inhibitor for studies on dopaminergic neurotransmission processes.

Toronto Research Chemicals - O857500

Quinolone antibacterial.

REFERENCES

• DiCarlo, et al.: Arch. Biochem. Biophys., 127, 503 (1968)
• Crew, et al.: Xenobiotica, 1, 193 (1968)
• Wright, H.T., et al.: Science, 213, 455 (1968)
• Turner, F.J. et al., Antimicrob. Agents Chemother., 1967, 475, (props)
• Kaminsky, D. et al., J. Med. Chem., 1968, 11, 160, (synth, pharmacol)
• Crew, M.C. et al., Xenobiotica, 1971, 1, 193, (metab)
• Biere, H. et al., Annalen, 1976, 1972, (synth)
• Mitscher, L.A. et al., J. Med. Chem., 1978, 21, 485, (synth)
• Glickman, R. et al., Am. J. Hosp. Pharm., 1979, 36, 1077, (rev)
• Katritzky, A.R. et al., Org. Magn. Reson., 1981, 16, 280, (cmr)
• Smrz, R. et al., Cesk. Farm., 1983, 32, 211, (synth)
• Cygler, M. et al., Acta Cryst. C, 1985, 41, 1052, (cryst struct)
• Granik, V.G. et al., Khim.-Farm. Zh., 1987, 21, 1249; CA, 109, 22333g, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2676, (synonyms)
• Betbeder, D. et al., Med. Sci. Res., 1988, 16, 141, (activity)
• Pesticide Manual, 9th edn., 1991, No. 9220
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A1262
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 189
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, OOG000