ChemFOnt: Showing chemical card for Enrofloxacin (CFc000011085)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:58:44 UTC

Chemfont ID

CFc000011085

Molecule Identification

Common Name

Enrofloxacin

Definition

Enrofloxacin is a veterinary antibacterial agent, used in poultry. Enrofloxacin is a fluoroquinolone antibiotic sold by the Bayer Corporation under the trade name Baytril(r). Enrofloxacin is currently FDA-approved for treatment of individual pets and domestic animals in the United States. In September 2005, the FDA withdrew approval of Baytril for use in water to treat flocks of poultry, as this practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium Campylobacter, a human pathogen. Fluoroquinolones such as ciprofloxacin are widely used in the treatment of human disease. Enrofloxacin is a synthetic chemotherapeutic agent from the class of the fluoroquinolone carboxylic acid derivatives. It has antibacterial activity against a broad spectrum of Gram-negative and Gram-positive bacteria. Its mechanism of action is not thoroughly understood, but it is believed to act by inhibiting bacterial DNA gyrase (a type-II topoisomerase), thereby preventing DNA supercoiling and DNA synthesis. It is a bactericidal agent. The bactericidal activity of enrofloxacin is concentration dependent, with susceptible bacteria cell death occurring within 20-30 minutes of exposure. Enrofloxacin has demonstrated a significant post-antibiotic effect for both Gram-negative and Gram-positive bacteria and is active in both stationary and growth phases of bacterial replication. http://www.fda.gov/cvm/Documents/baytrilDDL.pdf is a broken lin

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Baytril	ChEBI
ERFX	Kegg
1-Cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 9ci	HMDB
Bay VP 2674	HMDB
CFPQ	HMDB
Endrofloxicin	HMDB
Enrofloxacine	HMDB
Enrofloxacino	HMDB
Enrofloxacinum	HMDB
Enroxil	HMDB
N-Ethylciprofloxacin	HMDB
Bay-VP-2674	HMDB

Chemical Formula

C₁₉H₂₂FN₃O₃

Average Molecular Weight

359.3947

Monoisotopic Molecular Weight

359.16451979

IUPAC Name

1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

baytril

CAS Registry Number

93106-60-6

SMILES

CCN1CCN(CC1)C1=CC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O

InChI Identifier

InChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26)

InChI Key

SPFYMRJSYKOXGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-3-carboxylic acid
Fluoroquinolone
N-arylpiperazine
Aminoquinoline
Haloquinoline
Dihydroquinolone
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Dialkylarylamine
Tertiary aliphatic/aromatic amine
N-alkylpiperazine
Benzenoid
Pyridine
Aryl fluoride
Piperazine
Aryl halide
1,4-diazinane
Vinylogous amide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Amine
Organic oxide
Organohalogen compound
Organofluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:35720 )
N-arylpiperazine (CHEBI:35720 )
cyclopropanes (CHEBI:35720 )
N-alkylpiperazine (CHEBI:35720 )
quinolone (CHEBI:35720 )
quinolinemonocarboxylic acid (CHEBI:35720 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029861)
Cytoplasm (HMDB: HMDB0029861)

Source

Exogenous

Exogenous (HMDB: HMDB0029861)

Food

Food (HMDB: HMDB0029861)

Endogenous

Endogenous (HMDB: HMDB0029861)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029861)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.61 g/L	ALOGPS
logP	0.58	ALOGPS
logP	1.15	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	6.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.98 m³·mol⁻¹	ChemAxon
Polarizability	37.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon