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)C(F)=C3C(=O)C(=CN(C4CC4)C3=C2F)C(O)=O

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 1064
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 1064

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 8429	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 8.616672E11
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 8429	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 8.616672E11

PubMed

Title	Date	PubMed
Pharmacokinetics of orbifloxacin and its concentration in body fluids and in endometrial tissues of mares.	2001 Jul	11480524
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	12489859
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.	2002 Feb	11874520
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using liquid chromatography-fluorescence-multiple mass spectrometry.	2002 Nov 15	12383483
Determination of plasma and skin concentrations of orbifloxacin in dogs with clinically normal skin and dogs with pyoderma.	2002 Winter	12584677
In vitro antimicrobial activity of orbifloxacin against Staphylococcus intermedius isolates from canine skin and ear infections.	2004 Aug	15120955
Modulation of cellular immune response by orbifloxacin in noninfected and E. coli-infected mice.	2005	16237956
Inhibitory effect of several fluoroquinolones on hepatic microsomal cytochrome P-450 1A activities in dogs.	2005 Dec	16343288
Multiresidue determination of fluoroquinolones in shrimp by liquid chromatography-fluorescence-mass spectrometry.	2005 Jul-Aug	16152936
Hepatocellular toxicosis associated with the alternate administration of carprofen and meloxicam in a siberian husky.	2005 Oct	16276063
The pharmacokinetics of orbifloxacin in the horse following oral and intravenous administration.	2006 Jun	16669863
Comparison of pharmacodynamic and pharmacokinetic indices of efficacy for 5 fluoroquinolones toward pathogens of dogs and cats.	2006 Nov-Dec	17186841
Efficacy of orbifloxacin tablets for the treatment of superficial and deep pyoderma due to Staphylococcus intermedius infection in dogs.	2006 Oct	17078249
Lack of inhibitory effects of several fluoroquinolones on cytochrome P-450 3A activities at clinical dosage in dogs.	2007 Feb	17217399
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2007 Jul	17970104
Antimicrobial testing of selected fluoroquinolones against Pseudomonas aeruginosa isolated from canine otitis.	2007 Nov-Dec	17975212
Pharmacokinetics and milk penetration of orbifloxacin after intravenous, subcutaneous, and intramuscular administration to lactating goats.	2007 Sep	17699040
Implementation of terbium-sensitized luminescence in sequential-injection analysis for automatic analysis of orbifloxacin.	2008 Dec	18958455
Pharmacokinetic-pharmacodynamic integration of orbifloxacin in rabbits after intravenous, subcutaneous and intramuscular administration.	2008 Feb	18177323
Multiresidue determination of quinolones in animal and fishery products by HPLC.	2008 Jun	18633210
Pharmacokinetics and milk penetration of orbifloxacin after intravenous and intramuscular injections to dromedary lactating camels (Camelus dromedaries).	2008 Jun	18471152
Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae.	2008 Jun	18471102
Quality by design, part III: study of curing process of sustained release coated products using NIR spectroscopy.	2008 Sep	18481309
Quality by design, part II: application of NIR spectroscopy to monitor the coating process for a pharmaceutical sustained release product.	2008 Sep	18481308
Quality by design, part I: application of NIR spectroscopy to monitor tablet manufacturing process.	2008 Sep	18300297
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.	2008 Sep 18	18395369
Human-to-dog transmission of methicillin-resistant Staphylococcus aureus.	2009 Aug	19751611
Pharmacokinetics and milk distribution characteristics of orbifloxacin following intravenous and intramuscular injection in lactating ewes.	2009 Aug	19614838
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009 Jan	19449537
Approaches for application of sub and supercritical fluid extraction for quantification of orbifloxacin from plasma and milk: application to disposition kinetics.	2009 Jan 5	19046687
Free-radical-induced oxidative and reductive degradation of fluoroquinolone pharmaceuticals: kinetic studies and degradation mechanism.	2009 Jul 9	19507813
Pharmacokinetics and pharmacokinetic/pharmacodynamic integration of orbifloxacin in Korean Hanwoo cattle.	2009 Jun	19646085
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009 Mar	19680903
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.	2010 Apr	20175091
Rapid determination of fluoroquinolone residues in honey by a microbiological screening method and liquid chromatography.	2010 Jul-Aug	20922969
Short communication: Fluoroquinolone susceptibility of Staphylococcus aureus strains isolated from caprine clinical mastitis in southeast Spain.	2010 Nov	20965339
Solvent-free microwave-assisted extraction of fluoroquinolones from soil and liquid chromatography-fluorescence determination.	2010 Nov 19	20950813
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.	2010 Sep-Oct	21140677

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 `Fri Dec 15 15:44:30 UTC 2023` Edited by `admin` on `Fri Dec 15 15:44:30 UTC 2023`
Record UNII	660932TPY6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

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

ORBAX

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA95

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

CFR

21 CFR 520.1616

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

CFR

21 CFR 524.1610

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

CFR

21 CFR 520.1618

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

NCI_THESAURUS

C795

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

Code System Code Type Description

EVMPD

SUB09454MIG

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

PRIMARY

SMS_ID

100000083324

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

INN

7025

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

DRUG BANK

DB11443

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

PRIMARY

CAS

113617-63-3

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

PRIMARY

WIKIPEDIA

ORBIFLOXACIN

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

DAILYMED

660932TPY6

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

PRIMARY

EPA CompTox

DTXSID7046201

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

NCI_THESAURUS

C72635

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

RXCUI

995897

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

RxNorm

NSC

758614

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

RS_ITEM_NUM

1478673

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

MERCK INDEX

m8227

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

Merck Index

FDA UNII

660932TPY6

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

ChEMBL

CHEMBL295433

Created by admin on Fri Dec 15 15:44:30 UTC 2023 , Edited by admin on Fri Dec 15 15:44:30 UTC 2023

PRIMARY

PUBCHEM

60605

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

MESH

C095163

Created by admin on Fri Dec 15 15:44:31 UTC 2023 , Edited by admin on Fri Dec 15 15:44:31 UTC 2023

PRIMARY

Related Record Type Details


					2899SY5GHK

DESFLUORO 5-HYDROXY ORBIFLOXACIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					XJC83A5BC5

1-CYCLOPROPYL-7-(CIS-3,5-DIMETHYLPIPERAZIN-1-YL)-6,8-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					GNN7YW3PJ2

1-CYCLOPROPYL-5,6,7,8-TETRAFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					QH7W5PWD8L

7-((2-AMINOPROPYL)AMINO)-1-CYCLOPROPYL-5,6-DIFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					9W49RM6XVT

DESCARBOXYL ORBIFLOXACIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					RDJ8NT5Q7D

1-CYCLOPROPYL-5,7-BIS(CIS-3,5-DIMETHYLPIPERAZIN-1-YL)6,8-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					DNE8F8DTN2

1-CYCLOPROPYL-5-(CIS-3,5-DIMETHYLPIPERAZIN-1-YL)-6,7,8-TRIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					660932TPY6

ORBIFLOXACIN

ACTIVE MOIETY

Details

SMILES

InChI

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

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

PubMed

Patents

Sample Use Guides

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