Rosoxacin

Identification

Generic Name
Rosoxacin
DrugBank Accession Number
DB00817
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 294.3047
Monoisotopic: 294.100442324
Chemical Formula
C17H14N2O3
Synonyms
  • 1-ethyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acid
  • Acrosoxacin
  • Rosoxacin
  • Rosoxacina
  • Rosoxacine
  • Rosoxacino
  • Rosoxacinum
External IDs
  • TO 133
  • Win 35213

Pharmacology

Indication

For the treatment of bacterial infection of respiratory tract, urinary tract, GI, CNS and immuno compromised patients.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

Rosoxacin binds to and inhibits the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

TargetActionsOrganism
ADNA gyrase subunit B
inhibitor
Escherichia coli (strain K12)
ADNA topoisomerase 4 subunit A
inhibitor
Escherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Rosoxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Rosoxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Rosoxacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Rosoxacin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Rosoxacin.
Food Interactions
Not Available

Products

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International/Other Brands
Eradacil (Sanofi-Aventis) / Roxadyl

Categories

ATC Codes
J01MB01 — Rosoxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Phenylpyridines / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
4-phenylpyridine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Dihydroquinoline / Dihydroquinolone / Heteroaromatic compound / Hydrocarbon derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
3Y1OT3J4NW
CAS number
40034-42-2
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0014955
KEGG Drug
D02305
PubChem Compound
287180
PubChem Substance
46508469
ChemSpider
253208
RxNav
35797
ChEBI
131715
ChEMBL
CHEMBL291157
ZINC
ZINC000000002042
Therapeutic Targets Database
DAP000929
PharmGKB
PA164776843
Wikipedia
Rosoxacin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)290 °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
logP1.89Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6Chemaxon
pKa (Strongest Basic)4.89Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-0090000000-7e0bd8194d1adb5fe029
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-0090000000-892b68ee044640972c2c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-006w-0090000000-5534281b432dbe1f4ac5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-ed23c2d93095b01307ca
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-feec9c26eb52839dd417
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-016s-0090000000-c5c07099ccda8e511bf5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0290000000-97a701762a1b298d9b9f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.9870959
predicted
DarkChem Lite v0.1.0
[M-H]-183.7852959
predicted
DarkChem Lite v0.1.0
[M-H]-166.2495
predicted
DeepCCS 1.0 (2019)
[M+H]+183.4541959
predicted
DarkChem Lite v0.1.0
[M+H]+184.3359959
predicted
DarkChem Lite v0.1.0
[M+H]+168.6075
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.8940959
predicted
DarkChem Lite v0.1.0
[M+Na]+183.4544959
predicted
DarkChem Lite v0.1.0
[M+Na]+175.47713
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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, inc...
Gene Name
gyrB
Uniprot ID
P0AES6
Uniprot Name
DNA gyrase subunit B
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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 th...
Gene Name
parC
Uniprot ID
P0AFI2
Uniprot Name
DNA topoisomerase 4 subunit A
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
This drug is a quinolone derivative, and these agents are known to inhibit CYP1A2.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [Article]
  2. English BA, Dortch M, Ereshefsky L, Jhee S: Clinically significant psychotropic drug-drug interactions in the primary care setting. Curr Psychiatry Rep. 2012 Aug;14(4):376-90. doi: 10.1007/s11920-012-0284-9. [Article]
  3. Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:44