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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20F3N3O3
Molecular Weight 395.3763
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORBIFLOXACIN

SMILES

C[C@@]1([H])CN(C[C@@]([H])(C)N1)c2c(c(c3c(c2F)n(cc(c3=O)C(=O)O)C4CC4)F)F

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 395.3763
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

861667200000
Curative
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

861667200000
PubMed

PubMed

TitleDatePubMed
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
Comparison of pharmacodynamic and pharmacokinetic indices of efficacy for 5 fluoroquinolones toward pathogens of dogs and cats.
2006 Nov-Dec
Pharmacokinetics and milk penetration of orbifloxacin after intravenous, subcutaneous, and intramuscular administration to lactating goats.
2007 Sep
[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
Pharmacokinetics and milk distribution characteristics of orbifloxacin following intravenous and intramuscular injection in lactating ewes.
2009 Aug
Pharmacokinetics and pharmacokinetic/pharmacodynamic integration of orbifloxacin in Korean Hanwoo cattle.
2009 Jun
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
Patents

Patents

Sample Use Guides

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
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 Jun 25 21:00:25 UTC 2021
Edited
by admin
on Fri Jun 25 21:00:25 UTC 2021
Record UNII
660932TPY6
Record Status Validated (UNII)
Record Version
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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
NSC-758614
Code English
ORBIFLOXACIN [MART.]
Common Name English
ORBIFLOXACIN [USP MONOGRAPH]
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
Classification Tree Code System Code
WHO-VATC QJ01MA95
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
CFR 21 CFR 520.1616
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
CFR 21 CFR 524.1610
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
CFR 21 CFR 520.1618
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
NCI_THESAURUS C795
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
Code System Code Type Description
EVMPD
SUB09454MIG
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
INN
7025
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
DRUG BANK
DB11443
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
CAS
113617-63-3
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
USP_CATALOG
1478673
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
ORBIFLOXACIN
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
EPA CompTox
113617-63-3
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
NCI_THESAURUS
C72635
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
RXCUI
995897
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M8227
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY Merck Index
FDA UNII
660932TPY6
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
ChEMBL
CHEMBL295433
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
PUBCHEM
60605
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
MESH
C095163
Created by admin on Fri Jun 25 21:00:25 UTC 2021 , Edited by admin on Fri Jun 25 21:00:25 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY