ContaminantDB: Grepafloxacin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:19:57 UTC

Update Date

2026-04-13 20:31:17 UTC

Accession Number

CHEM022098

Identification

Common Name

Grepafloxacin

Class

Small Molecule

Description

Grepafloxacin is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Due to the QTc-prolonging potential, as indicated by the changes in the QT interval on the electrocardiogram, and the risk for cardiovascular adverse events, grepafloxacin was withdrawn in the United States.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Raxar	ChEMBL, HMDB
Grepafloxacin hydrochloride	MeSH, HMDB
Grepafloxacin HCL	MeSH, HMDB
(+--)-1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid	MeSH, HMDB
(+--)-1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid monohydrochloride	MeSH, HMDB

Chemical Formula

C₁₉H₂₂FN₃O₃

Average Molecular Mass

359.395 g/mol

Monoisotopic Mass

359.165 g/mol

CAS Registry Number

119914-60-2

IUPAC Name

1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

grepafloxacin

SMILES

CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O

InChI Identifier

InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)

InChI Key

AIJTTZAVMXIJGM-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
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aryl fluoride
Aryl halide
1,4-diazinane
Piperazine
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Tertiary amine
Azacycle
Secondary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Secondary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:5543 )
quinolone antibiotic (CHEBI:5543 )
fluoroquinolone antibiotic (CHEBI:5543 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	0.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.88	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	37.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr6-1029000000-706de57181850354ad84	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014l-4009700000-5f8c566ab4608e488a1d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-2f5a30d953de1f736ea3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-7029000000-5092d7ae0d6cd5b524bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9030000000-c160b8ef525b23358374	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-0009000000-21915b34d4523001f7f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2079000000-ac0604da9e8b550b1711	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9040000000-825d27f7dab3d78603bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-714280bbcfde93aa7b44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0019000000-5e38035e60ddc6c31a50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1098000000-13c3d9c32132c12b9af2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-eb6c80e8b1d8eb060c07	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-d1bdf823b553634a98a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-1094000000-f623c32b7e5523cef0dc	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00365

HMDB ID

HMDB0259429

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Grepafloxacin

Chemspider ID

65391

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C11368

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Grepafloxacin (CHEM022098)

Structure for CHEM022098: Grepafloxacin