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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20F3N3O3
Molecular Weight 395.3756
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORBIFLOXACIN

SMILES

C[C@H]1CN(C[C@@H](C)N1)C2=C(F)C3=C(C(=O)C(=CN3C4CC4)C(O)=O)C(F)=C2F

InChI

InChIKey=QIPQASLPWJVQMH-DTORHVGOSA-N
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+

HIDE SMILES / InChI

Description

Orbifloxacin (brand name Orbax) is a fluoroquinolone antibiotic which is approved for use in dogs and cats, abd marketed by Schering-Plough Animal Health. Orbifloxacin is a synthetic broad-spectrum antibacterial agent from the class of fluoroquinolone carboxylic acid derivatives. Orbifloxacin is the international nonproprietary name for 1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-7-(cis-3,5-dimethyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid. ORBAX® Oral Suspension is a malt flavored antibiotic suspension containing 30 mg/mL of orbifloxacin and sorbic acid as a preservative. ORBAX® Oral Suspension is indicated for the treatment of urinary tract infections (cystitis) and also for skin and soft tissue infections (wounds and abscesses). Orbifloxacin is bactericidal against a wide range of gram-negative and gram-positive organisms and exerts its antibacterial effect through interference with the bacterial enzyme DNA gyrase which is needed for the maintenance and synthesis of bacterial DNA.

CNS Activity

Originator

Target Info

Target Info

Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
ORBAX
Primary
ORBAX
PMID

PMID

TitleDatePMID
Pharmacokinetics of orbifloxacin and its concentration in body fluids and in endometrial tissues of mares.
2001 Jul
Determination of quinolones and fluoroquinolones in fish tissue and seafood by high-performance liquid chromatography with electrospray ionisation tandem mass spectrometric detection.
2002 Dec 20
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.
2002 Feb
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using liquid chromatography-fluorescence-multiple mass spectrometry.
2002 Nov 15
Determination of plasma and skin concentrations of orbifloxacin in dogs with clinically normal skin and dogs with pyoderma.
2002 Winter
In vitro antimicrobial activity of orbifloxacin against Staphylococcus intermedius isolates from canine skin and ear infections.
2004 Aug
Modulation of cellular immune response by orbifloxacin in noninfected and E. coli-infected mice.
2005
Inhibitory effect of several fluoroquinolones on hepatic microsomal cytochrome P-450 1A activities in dogs.
2005 Dec
Multiresidue determination of fluoroquinolones in shrimp by liquid chromatography-fluorescence-mass spectrometry.
2005 Jul-Aug
Hepatocellular toxicosis associated with the alternate administration of carprofen and meloxicam in a siberian husky.
2005 Oct
The pharmacokinetics of orbifloxacin in the horse following oral and intravenous administration.
2006 Jun
Comparison of pharmacodynamic and pharmacokinetic indices of efficacy for 5 fluoroquinolones toward pathogens of dogs and cats.
2006 Nov-Dec
Efficacy of orbifloxacin tablets for the treatment of superficial and deep pyoderma due to Staphylococcus intermedius infection in dogs.
2006 Oct
Lack of inhibitory effects of several fluoroquinolones on cytochrome P-450 3A activities at clinical dosage in dogs.
2007 Feb
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].
2007 Jul
Antimicrobial testing of selected fluoroquinolones against Pseudomonas aeruginosa isolated from canine otitis.
2007 Nov-Dec
Pharmacokinetics and milk penetration of orbifloxacin after intravenous, subcutaneous, and intramuscular administration to lactating goats.
2007 Sep
Implementation of terbium-sensitized luminescence in sequential-injection analysis for automatic analysis of orbifloxacin.
2008 Dec
Pharmacokinetic-pharmacodynamic integration of orbifloxacin in rabbits after intravenous, subcutaneous and intramuscular administration.
2008 Feb
[Multiresidue determination of quinolones in animal and fishery products by HPLC].
2008 Jun
Pharmacokinetics and milk penetration of orbifloxacin after intravenous and intramuscular injections to dromedary lactating camels (Camelus dromedaries).
2008 Jun
Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae.
2008 Jun
Quality by design, part III: study of curing process of sustained release coated products using NIR spectroscopy.
2008 Sep
Quality by design, part II: application of NIR spectroscopy to monitor the coating process for a pharmaceutical sustained release product.
2008 Sep
Quality by design, part I: application of NIR spectroscopy to monitor tablet manufacturing process.
2008 Sep
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.
2008 Sep 18
Human-to-dog transmission of methicillin-resistant Staphylococcus aureus.
2009 Aug
Pharmacokinetics and milk distribution characteristics of orbifloxacin following intravenous and intramuscular injection in lactating ewes.
2009 Aug
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].
2009 Jan
Approaches for application of sub and supercritical fluid extraction for quantification of orbifloxacin from plasma and milk: application to disposition kinetics.
2009 Jan 5
Free-radical-induced oxidative and reductive degradation of fluoroquinolone pharmaceuticals: kinetic studies and degradation mechanism.
2009 Jul 9
Pharmacokinetics and pharmacokinetic/pharmacodynamic integration of orbifloxacin in Korean Hanwoo cattle.
2009 Jun
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.
2009 Mar
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.
2010 Apr
Rapid determination of fluoroquinolone residues in honey by a microbiological screening method and liquid chromatography.
2010 Jul-Aug
Short communication: Fluoroquinolone susceptibility of Staphylococcus aureus strains isolated from caprine clinical mastitis in southeast Spain.
2010 Nov
Solvent-free microwave-assisted extraction of fluoroquinolones from soil and liquid chromatography-fluorescence determination.
2010 Nov 19
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.
2010 Sep-Oct
Patent

Patent

Sample Use Guides

In Vivo Use Guide
for dogs: oral Suspension is 1.1 to 3.4 mg/lb (2.5 to 7.5 mg/kg) of body weight administered once daily
Route of Administration: Oral
In Vitro Use Guide
The minimum inhibitory concentrations (MICs) of orbifloxacin against 240 field S. intermedius isolates (69 skin and 171 ear isolates) ranged from 0.016 to 8 mg l(-1), with MIC50 and MIC90 equal to 0.5 and 1 mg l(-1), respectively.
Name Type Language
ORBIFLOXACIN
GREEN BOOK   INN   MART.   MI   USP   USP-RS  
INN  
Official Name English
ORBIFLOXACIN [USP-RS]
Common Name English
ORBIFLOXACIN [MI]
Common Name English
ORBIFLOXACIN [GREEN BOOK]
Common Name English
ORBIFLOXACIN [MART.]
Common Name English
ORBIFLOXACIN [INN]
Common Name English
1-CYCLOPROPYL-7-(CIS-3,5-DIMETHYL-1-PIPERAZINYL)-5,6,8-TRIFLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID
Systematic Name English
ORBIFLOXACIN [USP]
Common Name English
ORBAX
Brand Name English
ORBIFLOXACIN [JAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01MA95
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
CFR 21 CFR 520.1616
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
CFR 21 CFR 524.1610
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
CFR 21 CFR 520.1618
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
Code System Code Type Description
EVMPD
SUB09454MIG
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
INN
7025
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
CAS
113617-63-3
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
WIKIPEDIA
ORBIFLOXACIN
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
EPA CompTox
113617-63-3
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
NCI_THESAURUS
C72635
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
RXCUI
995897
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M8227
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL295433
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY
PUBCHEM
60605
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY SWITZERF
MESH
C095163
Created by admin on Tue Mar 06 11:25:18 UTC 2018 , Edited by admin on Tue Mar 06 11:25:18 UTC 2018
PRIMARY