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
Structure for Rosoxacin (DB00817)
- 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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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ADNA gyrase subunit B inhibitorEscherichia coli (strain K12) ADNA topoisomerase 4 subunit A inhibitorEscherichia 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Rosoxacin. Aceclofenac Aceclofenac may increase the neuroexcitatory activities of Rosoxacin. Acemetacin Acemetacin may increase the neuroexcitatory activities of Rosoxacin. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Rosoxacin. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Rosoxacin. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Eradacil (Sanofi-Aventis) / Roxadyl
Categories
- ATC Codes
- J01MB01 — Rosoxacin
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Fluoroquinolones
- Heterocyclic Compounds, Fused-Ring
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Quinolines
- 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
- External Links
- Human Metabolome Database
- HMDB0014955
- KEGG Drug
- D02305
- PubChem Compound
- 287180
- PubChem Substance
- 46508469
- ChemSpider
- 253208
- 35797
- ChEBI
- 131715
- ChEMBL
- CHEMBL291157
- ZINC
- ZINC000000002042
- Therapeutic Targets Database
- DAP000929
- PharmGKB
- PA164776843
- Wikipedia
- Rosoxacin
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 290 °C PhysProp water solubility 0.0209 mg/mL at 25 °C MEYLAN,WM et al. (1996) logP 3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.102 mg/mL ALOGPS logP 1.85 ALOGPS logP 1.89 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 6 Chemaxon pKa (Strongest Basic) 4.89 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 70.5 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 83.06 m3·mol-1 Chemaxon Polarizability 30.8 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9953 Blood Brain Barrier + 0.8044 Caco-2 permeable + 0.6365 P-glycoprotein substrate Non-substrate 0.5522 P-glycoprotein inhibitor I Non-inhibitor 0.8418 P-glycoprotein inhibitor II Non-inhibitor 0.7855 Renal organic cation transporter Non-inhibitor 0.8055 CYP450 2C9 substrate Non-substrate 0.7741 CYP450 2D6 substrate Non-substrate 0.8696 CYP450 3A4 substrate Non-substrate 0.7172 CYP450 1A2 substrate Non-inhibitor 0.7953 CYP450 2C9 inhibitor Non-inhibitor 0.864 CYP450 2D6 inhibitor Non-inhibitor 0.9328 CYP450 2C19 inhibitor Non-inhibitor 0.8731 CYP450 3A4 inhibitor Non-inhibitor 0.9181 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7267 Ames test Non AMES toxic 0.8588 Carcinogenicity Non-carcinogens 0.8638 Biodegradation Not ready biodegradable 0.9751 Rat acute toxicity 2.3043 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9583 hERG inhibition (predictor II) Non-inhibitor 0.8496
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004i-0090000000-7e0bd8194d1adb5fe029 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002b-0090000000-892b68ee044640972c2c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-006w-0090000000-5534281b432dbe1f4ac5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-ed23c2d93095b01307ca Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0090000000-feec9c26eb52839dd417 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-016s-0090000000-c5c07099ccda8e511bf5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0290000000-97a701762a1b298d9b9f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.9870959 predictedDarkChem Lite v0.1.0 [M-H]- 183.7852959 predictedDarkChem Lite v0.1.0 [M-H]- 166.2495 predictedDeepCCS 1.0 (2019) [M+H]+ 183.4541959 predictedDarkChem Lite v0.1.0 [M+H]+ 184.3359959 predictedDarkChem Lite v0.1.0 [M+H]+ 168.6075 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.8940959 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.4544959 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.47713 predictedDeepCCS 1.0 (2019)
Targets
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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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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]
- 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]
- 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