Orbifloxacin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Orbifloxacin
Accession Number
DB11443
Type
Small Molecule
Groups
Vet approved
Description

Orbifloxacin is a fluoroquinolone antibiotic. It is marketed by Schering-Plough Animal Health and approved for certain infections in dogs.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Orbax
Categories
UNII
660932TPY6
CAS number
113617-63-3
Weight
Average: 395.382
Monoisotopic: 395.145676005
Chemical Formula
C19H20F3N3O3
InChI Key
QIPQASLPWJVQMH-DTORHVGOSA-N
InChI
InChI=1S/C19H20F3N3O3/c1-8-5-24(6-9(2)23-8)17-14(21)13(20)12-16(15(17)22)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6H2,1-2H3,(H,27,28)/t8-,9+
IUPAC Name
1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
[H][C@]1(C)CN(C[C@@]([H])(C)N1)C1=C(F)C(F)=C2C(=O)C(=CN(C3CC3)C2=C1F)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Orbifloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Orbifloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Orbifloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Orbifloxacin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Orbifloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Orbifloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Orbifloxacin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Orbifloxacin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Orbifloxacin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Orbifloxacin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Harada K, Shimizu T, Kataoka Y, Takahashi T: Post-antibiotic effect of orbifloxacin against Escherichia coli and Pseudomonas aeruginosa isolates from dogs. Acta Vet Scand. 2012 Mar 20;54:16. doi: 10.1186/1751-0147-54-16. [PubMed:22433170]
  2. Haines GR, Brown MP, Gronwall RR, Merritt KA, Baltzley LK: Pharmacokinetics of orbifloxacin and its concentration in body fluids and in endometrial tissues of mares. Can J Vet Res. 2001 Jul;65(3):181-7. [PubMed:11480524]
  3. Llorent-Martinez EJ, Ortega-Barrales P, Molina-Diaz A, Ruiz-Medina A: Implementation of terbium-sensitized luminescence in sequential-injection analysis for automatic analysis of orbifloxacin. Anal Bioanal Chem. 2008 Dec;392(7-8):1397-403. doi: 10.1007/s00216-008-2434-9. Epub 2008 Oct 29. [PubMed:18958455]
  4. Morimura T, Nobuhara Y, Matsukura H: Photodegradation products of a new antibacterial fluoroquinolone derivative, orbifloxacin, in aqueous solution. Chem Pharm Bull (Tokyo). 1997 Feb;45(2):373-7. [PubMed:9118451]
  5. Morimura T, Ohno T, Matsukura H, Nobuhara Y: Photodegradation kinetics of the new antibacterial fluoroquinolone derivative, orbifloxacin, in aqueous solution. Chem Pharm Bull (Tokyo). 1995 Jun;43(6):1000-4. [PubMed:7641301]
  6. Szczypka M, Gaweda B, Obminska-Mrukowicz B: Modulation of cellular immune response by orbifloxacin in noninfected and E. coli-infected mice. Immunopharmacol Immunotoxicol. 2005;27(3):461-72. [PubMed:16237956]
  7. Davis JL, Papich MG, Weingarten A: The pharmacokinetics of orbifloxacin in the horse following oral and intravenous administration. J Vet Pharmacol Ther. 2006 Jun;29(3):191-7. [PubMed:16669863]
  8. Gebru E, Lee SJ, Kim JC, Park SC: Allometric scaling of orbifloxacin disposition in nine mammal species: a retrospective analysis. J Vet Med Sci. 2011 Jun;73(6):817-20. Epub 2011 Jan 12. [PubMed:21233597]
  9. Hawkins MG, Taylor IT, Byrne BA, Armstrong RD, Tell LA: Pharmacokinetic-pharmacodynamic integration of orbifloxacin in Japanese quail (Coturnix japonica) following oral and intravenous administration. J Vet Pharmacol Ther. 2011 Aug;34(4):350-8. doi: 10.1111/j.1365-2885.2010.01233.x. Epub 2010 Oct 11. [PubMed:20950349]
External Links
KEGG Drug
D08299
ChemSpider
54631
ChEMBL
CHEMBL295433
Wikipedia
Orbifloxacin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0254 mg/mLALOGPS
logP0.36ALOGPS
logP0.25ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.49ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.21 m3·mol-1ChemAxon
Polarizability37.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Aryl fluorides / Benzenoids
show 13 more
Substituents
Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Dialkylarylamine
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

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. 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. [PubMed:21190921]
  2. Fuhr U, Strobl G, Manaut F, Anders EM, Sorgel F, Lopez-de-Brinas E, Chu DT, Pernet AG, Mahr G, Sanz F, et al.: Quinolone antibacterial agents: relationship between structure and in vitro inhibition of the human cytochrome P450 isoform CYP1A2. Mol Pharmacol. 1993 Feb;43(2):191-9. [PubMed:8429824]
  3. Get to Know an Enzyme: CYP1A2 [Link]

Drug created on February 25, 2016 11:49 / Updated on June 04, 2019 07:21