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Identification
NameRosoxacin
Accession NumberDB00817  (APRD00369)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
Acrosoxacin
ROS
Rosoxacin
Rosoxacine
Rosoxacino
Rosoxacinum
Roxadyl
External Identifiers
  • TO 133
  • Win 35213
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EradacilSanofi-Aventis
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII3Y1OT3J4NW
CAS number40034-42-2
WeightAverage: 294.3047
Monoisotopic: 294.100442324
Chemical FormulaC17H14N2O3
InChI KeyInChIKey=XBPZXDSZHPDXQU-UHFFFAOYSA-N
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)
IUPAC Name
1-ethyl-4-oxo-7-(pyridin-4-yl)-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CCN1C=C(C(O)=O)C(=O)C2=C1C=C(C=C2)C1=CC=NC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • 4-phenylpyridine
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of bacterial infection of respiratory tract, urinary tract, GI, CNS and immuno compromised patients.
PharmacodynamicsRosoxacin 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.
Mechanism of actionRosoxacin binds to and inhibits the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9953
Blood Brain Barrier+0.8044
Caco-2 permeable+0.6365
P-glycoprotein substrateNon-substrate0.5522
P-glycoprotein inhibitor INon-inhibitor0.8418
P-glycoprotein inhibitor IINon-inhibitor0.7855
Renal organic cation transporterNon-inhibitor0.8055
CYP450 2C9 substrateNon-substrate0.7741
CYP450 2D6 substrateNon-substrate0.8696
CYP450 3A4 substrateNon-substrate0.7172
CYP450 1A2 substrateNon-inhibitor0.7953
CYP450 2C9 inhibitorNon-inhibitor0.864
CYP450 2D6 inhibitorNon-inhibitor0.9328
CYP450 2C19 inhibitorNon-inhibitor0.8731
CYP450 3A4 inhibitorNon-inhibitor0.9181
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7267
Ames testNon AMES toxic0.8588
CarcinogenicityNon-carcinogens0.8638
BiodegradationNot ready biodegradable0.9751
Rat acute toxicity2.3043 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9583
hERG inhibition (predictor II)Non-inhibitor0.8496
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point290 °CPhysProp
water solubility0.0209 mg/mL at 25 °CMEYLAN,WM et al. (1996)
logP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.102 mg/mLALOGPS
logP1.85ALOGPS
logP1.9ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.18ChemAxon
pKa (Strongest Basic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.5 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.06 m3·mol-1ChemAxon
Polarizability30.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01MB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Magnesium ion binding
Specific Function:
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, including catenanes and knotted rings.
Gene Name:
gyrB
Uniprot ID:
P0AES6
Molecular Weight:
89949.195 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Zweerink MM, Edison A: Inhibition of Micrococcus luteus DNA gyrase by norfloxacin and 10 other quinolone carboxylic acids. Antimicrob Agents Chemother. 1986 Apr;29(4):598-601. [PubMed:3010848 ]
  4. Hirai K, Aoyama H, Suzue S, Irikura T, Iyobe S, Mitsuhashi S: Isolation and characterization of norfloxacin-resistant mutants of Escherichia coli K-12. Antimicrob Agents Chemother. 1986 Aug;30(2):248-53. [PubMed:3532944 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function:
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule. MukB stimulates the relaxation activity of topoisomerase IV and also has a modest effect on decatenation.
Gene Name:
parC
Uniprot ID:
P0AFI2
Molecular Weight:
83830.455 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Zweerink MM, Edison A: Inhibition of Micrococcus luteus DNA gyrase by norfloxacin and 10 other quinolone carboxylic acids. Antimicrob Agents Chemother. 1986 Apr;29(4):598-601. [PubMed:3010848 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23