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

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	MOL RATIO 1 MOL RATIO (average)

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

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.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 26	Binding Agent 1,076
DNA gyrase 26	Binding Agent 1,076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections (cystitis) 3	Curative		Approved 8,583	ORBAX
Skin and soft tissue infections 33	Curative		Approved 8,583	ORBAX

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 inducer 1,087	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP1A2 2,153 CYP2C19 2,057	P-gp 2,052

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP19A1 430	inhibitor 4,027	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2,052	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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PubMed

Show entries

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

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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.