ORBIFLOXACIN

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 Search

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

Molecular Formula	C19H20F3N3O3
Molecular Weight	395.3756
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4a4cabca-caa0-4df3-bc46-963f0804b54a&type=display
Curator's Comment: description was created based on several sources, including

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.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 26 Target ID: CHEMBL3038482 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4a4cabca-caa0-4df3-bc46-963f0804b54a&type=display	Binding Agent 1076
DNA gyrase 26 Target ID: CHEMBL2094139 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4a4cabca-caa0-4df3-bc46-963f0804b54a&type=display	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections (cystitis) 3 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4a4cabca-caa0-4df3-bc46-963f0804b54a&type=display	Curative		Approved 8583	ORBAX Approved Use Oral Suspension is indicated for the treatment of urinary tract infections (cystitis) in dogs caused by susceptible strains of Staphylococcus pseudintermedius, Proteus mirabilis, Escherichia coli and Enterococcus faecalis. ORBAX® Oral Suspension is also indicated for skin and soft tissue infections (wounds and abscesses) in dogs caused by susceptible strains of Staphylococcus pseudintermedius, Staphylococcus aureus, coagulase positive staphylococci, Pasteurella multocida, Proteus mirabilis, Pseudomonas spp., Klebsiella pneumoniae, Escherichia coli, Enterobacter spp., Citrobacter spp., Enterococcus faecalis, β-hemolytic streptococci (Group G) and Streptococcus equisimilis. Launch Date 1997
Skin and soft tissue infections 33 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4a4cabca-caa0-4df3-bc46-963f0804b54a&type=display	Curative		Approved 8583	ORBAX Approved Use Oral Suspension is indicated for the treatment of urinary tract infections (cystitis) in dogs caused by susceptible strains of Staphylococcus pseudintermedius, Proteus mirabilis, Escherichia coli and Enterococcus faecalis. ORBAX® Oral Suspension is also indicated for skin and soft tissue infections (wounds and abscesses) in dogs caused by susceptible strains of Staphylococcus pseudintermedius, Staphylococcus aureus, coagulase positive staphylococci, Pasteurella multocida, Proteus mirabilis, Pseudomonas spp., Klebsiella pneumoniae, Escherichia coli, Enterobacter spp., Citrobacter spp., Enterococcus faecalis, β-hemolytic streptococci (Group G) and Streptococcus equisimilis. Launch Date 1997

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP1A2 2153 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 173.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 240.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 240.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 230.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 229.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 202.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 225.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 200 \| 202	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/60605#section=BioAssay-Results Page: 240.0

PubMed

Title	Date	PubMed
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.	2010-12-15	21140677
Solvent-free microwave-assisted extraction of fluoroquinolones from soil and liquid chromatography-fluorescence determination.	2010-11-19	20950813
Short communication: Fluoroquinolone susceptibility of Staphylococcus aureus strains isolated from caprine clinical mastitis in southeast Spain.	2010-11	20965339
Rapid determination of fluoroquinolone residues in honey by a microbiological screening method and liquid chromatography.	2010-10-07	20922969
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.	2010-04	20175091
Human-to-dog transmission of methicillin-resistant Staphylococcus aureus.	2009-08	19751611
Pharmacokinetics and milk distribution characteristics of orbifloxacin following intravenous and intramuscular injection in lactating ewes.	2009-08	19614838
Free-radical-induced oxidative and reductive degradation of fluoroquinolone pharmaceuticals: kinetic studies and degradation mechanism.	2009-07-09	19507813
Pharmacokinetics and pharmacokinetic/pharmacodynamic integration of orbifloxacin in Korean Hanwoo cattle.	2009-06	19646085
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009-03	19680903
Approaches for application of sub and supercritical fluid extraction for quantification of orbifloxacin from plasma and milk: application to disposition kinetics.	2009-01-05	19046687
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009-01	19449537
Implementation of terbium-sensitized luminescence in sequential-injection analysis for automatic analysis of orbifloxacin.	2008-12	18958455
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.	2008-09-18	18395369
Quality by design, part III: study of curing process of sustained release coated products using NIR spectroscopy.	2008-09	18481309
Quality by design, part II: application of NIR spectroscopy to monitor the coating process for a pharmaceutical sustained release product.	2008-09	18481308
Quality by design, part I: application of NIR spectroscopy to monitor tablet manufacturing process.	2008-09	18300297
[Multiresidue determination of quinolones in animal and fishery products by HPLC].	2008-06	18633210
Pharmacokinetics and milk penetration of orbifloxacin after intravenous and intramuscular injections to dromedary lactating camels (Camelus dromedaries).	2008-06	18471152
Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae.	2008-06	18471102
Pharmacokinetic-pharmacodynamic integration of orbifloxacin in rabbits after intravenous, subcutaneous and intramuscular administration.	2008-02	18177323
Antimicrobial testing of selected fluoroquinolones against Pseudomonas aeruginosa isolated from canine otitis.	2007-11-03	17975212
Pharmacokinetics and milk penetration of orbifloxacin after intravenous, subcutaneous, and intramuscular administration to lactating goats.	2007-09	17699040
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2007-07	17970104
Lack of inhibitory effects of several fluoroquinolones on cytochrome P-450 3A activities at clinical dosage in dogs.	2007-02	17217399
Comparison of pharmacodynamic and pharmacokinetic indices of efficacy for 5 fluoroquinolones toward pathogens of dogs and cats.	2006-12-26	17186841
Efficacy of orbifloxacin tablets for the treatment of superficial and deep pyoderma due to Staphylococcus intermedius infection in dogs.	2006-10	17078249
The pharmacokinetics of orbifloxacin in the horse following oral and intravenous administration.	2006-06	16669863
Inhibitory effect of several fluoroquinolones on hepatic microsomal cytochrome P-450 1A activities in dogs.	2005-12	16343288
Hepatocellular toxicosis associated with the alternate administration of carprofen and meloxicam in a siberian husky.	2005-10	16276063
Multiresidue determination of fluoroquinolones in shrimp by liquid chromatography-fluorescence-mass spectrometry.	2005-09-13	16152936
Modulation of cellular immune response by orbifloxacin in noninfected and E. coli-infected mice.	2005	16237956
In vitro antimicrobial activity of orbifloxacin against Staphylococcus intermedius isolates from canine skin and ear infections.	2004-08	15120955
Determination of quinolones and fluoroquinolones in fish tissue and seafood by high-performance liquid chromatography with electrospray ionisation tandem mass spectrometric detection.	2002-12-20	12489859
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using liquid chromatography-fluorescence-multiple mass spectrometry.	2002-11-15	12383483
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.	2002-02	11874520
Determination of plasma and skin concentrations of orbifloxacin in dogs with clinically normal skin and dogs with pyoderma.	2002	12584677
Pharmacokinetics of orbifloxacin and its concentration in body fluids and in endometrial tissues of mares.	2001-07	11480524

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:15 GMT 2025`
Record UNII	660932TPY6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ORBAX

Preferred Name

English

ORBIFLOXACIN

Official Name

English

ORBIFLOXACIN [USP-RS]

Common Name

English

ORBIFLOXACIN [MI]

Common Name

English

ORBIFLOXACIN [GREEN BOOK]

Common Name

English

NSC-758614

Code

English

ORBIFLOXACIN [MART.]

Common Name

English

ORBIFLOXACIN [USP MONOGRAPH]

Common Name

English

orbifloxacin [INN]

Common Name

English

ORBIFLOXACIN [JAN]

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 IMPURITY]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA95