ChemFOnt: Showing chemical card for Flumequine (CFc000022729)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:10 UTC

Chemfont ID

CFc000022729

Molecule Identification

Common Name

Flumequine

Definition

Ciprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division. Flumequine is a 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The molecular formula is C14H12FNO3 It is a white powder, odorless, flavorless, insoluble in water but soluble in organic solvent. Flumequine is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed. It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries. It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone. However this was a limited indication because only minimal serum levels were achieved. The first quinolone used was nalidixic acid (was marketed in many countries as Negram) followed by the fluoroquinolone flumequine. The first-generation fluoroquinolone agents, such as flumequine, had poor distribution into the body tissues and limited activity. As such they were used mainly for treatment of urinary tract infections. Flumequine (benzo quinolizine) was first patented in 1973, (German Patent) by Rikker Labs. Flumequine is a known antimicrobial compound described and claimed in U.S. Pat. No. 3,896,131 (Example 3), July 22, 1975. Flumequine is the first quinolone compound with a fluorine atom at the C6-position of the related quinolone basic molecular structure. Even though this was the first fluoroquinolone, it is oftentimes overlooked when classifying the drugs within this class by generations and excluded from such a list. There continues to be considerable debate as to whether or not this DNA damage is to be considered one of the mechanisms of action concerning the severe adverse reactions experienced by some patients following fluoroquinolone therapy.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
FLM	Kegg
Apurone	Kegg
9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate	HMDB
Flumequine	MeSH

Chemical Formula

C₁₄H₁₂FNO₃

Average Molecular Weight

261.2484

Monoisotopic Molecular Weight

261.08012146

IUPAC Name

7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0⁵,¹³]trideca-2,5(13),6,8-tetraene-3-carboxylic acid

Traditional Name

flumequine

CAS Registry Number

42835-25-6

SMILES

CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O

InChI Identifier

InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)

InChI Key

DPSPPJIUMHPXMA-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
Dihydroquinolone
Haloquinoline
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Benzenoid
Pyridine
Aryl fluoride
Aryl halide
Vinylogous amide
Heteroaromatic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:85269 )
quinolone antibiotic (CHEBI:85269 )
3-oxo monocarboxylic acid (CHEBI:85269 )
pyridoquinoline (CHEBI:85269 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041895)

Source

Exogenous

Exogenous (HMDB: HMDB0041895)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	1.62	ALOGPS
logP	2.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.87 m³·mol⁻¹	ChemAxon
Polarizability	25.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041895

DrugBank ID

DB08972

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flumequine

METLIN ID

Not Available

PubChem Compound

3374

PDB ID

Not Available

ChEBI ID

85269

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Flumequine (CFc000022729)

MOL for CFc000022729 (Flumequine)

3D MOL for CFc000022729 (Flumequine)

3D SDF for CFc000022729 (Flumequine)

3D-SDF for CFc000022729 (Flumequine)

PDB for CFc000022729 (Flumequine)

3D PDB for CFc000022729 (Flumequine)

SMILES for CFc000022729 (Flumequine)

INCHI for CFc000022729 (Flumequine)

Structure for CFc000022729 (Flumequine)

3D Structure for CFc000022729 (Flumequine)