1-ethyl-4-oxo-7-(pyridin-4-yl)-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 696
• Molecular Formular: C17H14N2O3
• Molecular Mass: 294.30466
• Monoisotopic Mass: 294.10044232
• SMILES: O=c1c2c(n(CC)cc1C(=O)O)cc(cc2)c1ccncc1
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc(cc2)c1ccncc1
• InChI: InChI=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)
• InChIKey: XBPZXDSZHPDXQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-4-oxo-7-(pyridin-4-yl)-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: rosoxacin
• Brand Name: Eracine; Eradacil; Eradacin; Roxadyl; Winuron
• Synonyms: ROS; Rosoxacino [INN-Spanish]; Rosoxacine [INN-French]; Acrosoxacin; Rosoxacin

Database IDs

• CAS Number: 40034-42-2
• PubChem SID: 160964159; 46508469
• PubChem CID: 287180

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.1820016
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.9825406
• LogD (pH = 7.4): 0.8942017
• Log P: 1.899295
• Molar Refractivity: 83.0557 cm^3
• Polarizability: 32.14734 Å^3
• Polar Surface Area: 70.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.85
• LOG S: -3.46
• Solubility (Water): 1.02e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.0209 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]
• Hydrophobicity(logP): 3

DETAILS

DrugBank - DB00817

• Drug Groups: approved
• Description: Rosoxacin is a quinolone derivative antibiotic for the treatment of bacterial infection of respiratory tract, urinary tract, GI, CNS and immuno compromised patients. Rosoxacin is known to be effective against penicillin resistant strains and is a single dose orally administered drug, which avoids all complications of parenteral administration seen with penicillin, especially anaphylactic shock.
• Indication: For the treatment of bacterial infection of respiratory tract, urinary tract, GI, CNS and immuno compromised patients.
• Pharmacology: Rosoxacin is a nonfluorinated quinolone antibiotic. Its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Rosoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.
• Affected Organisms: Enteric bacteria and other eubacteria