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

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 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 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 1997

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
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
Hepatocellular toxicosis associated with the alternate administration of carprofen and meloxicam in a siberian husky.	2005 Oct	16276063
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
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
Quality by design, part II: application of NIR spectroscopy to monitor the coating process for a pharmaceutical sustained release product.	2008 Sep	18481308
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009 Jan	19449537
Free-radical-induced oxidative and reductive degradation of fluoroquinolone pharmaceuticals: kinetic studies and degradation mechanism.	2009 Jul 9	19507813
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.

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

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CFR

21 CFR 520.1616

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CFR

21 CFR 524.1610

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CFR

21 CFR 520.1618

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NCI_THESAURUS

C795

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Code System Code Type Description

EVMPD

SUB09454MIG

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SMS_ID

100000083324

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INN

7025

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DRUG BANK

DB11443

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CAS

113617-63-3

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WIKIPEDIA

ORBIFLOXACIN

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DAILYMED

660932TPY6

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EPA CompTox

DTXSID7046201

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NCI_THESAURUS

C72635

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RXCUI

995897

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RxNorm

NSC

758614

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RS_ITEM_NUM

1478673

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MERCK INDEX

m8227

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Merck Index

FDA UNII

660932TPY6

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ChEMBL

CHEMBL295433

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PUBCHEM

60605

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MESH

C095163

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ACTIVE MOIETY


					660932TPY6

ORBIFLOXACIN

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