ContaminantDB: Gatifloxacin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:15 UTC

Update Date

2026-03-26 22:58:59 UTC

Accession Number

CHEM002331

Identification

Common Name

Gatifloxacin

Class

Small Molecule

Description

Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin™ for the treatment of respiratory tract infections, having licensed the medication from Kyorin Pharmaceutical Company of Japan. Allergan produces an eye-drop formulation called Zymar™. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. [Wikipedia]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Infective Agent
Antibiotic
Drug
Ester
Ether
Metabolite
Organic Compound
Organofluoride
Quinolone
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid	ChEBI
1-Cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid	ChEBI
AM 1155	ChEBI
Gatifloxacine	ChEBI
Gatifloxacino	ChEBI
Gatifloxacinum	ChEBI
Gatifloxacin anhydrous	Kegg
Zymer	Kegg
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate	Generator
1-Cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylate	Generator
Tequin	MeSH
Zymar	MeSH

Chemical Formula

C₁₉H₂₂FN₃O₄

Average Molecular Mass

375.394 g/mol

Monoisotopic Mass

375.159 g/mol

CAS Registry Number

112811-59-3

IUPAC Name

1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

gatifloxacin

SMILES

COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1

InChI Identifier

InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:5280 )
N-arylpiperazine (CHEBI:5280 )
quinolone antibiotic (CHEBI:5280 )
quinolone (CHEBI:5280 )
quinolinemonocarboxylic acid (CHEBI:5280 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	182-185°C
Boiling Point	Not Available
Solubility	60 mg/mL (at pH 4)

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-0.58	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	8.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.82 m³·mol⁻¹	ChemAxon
Polarizability	38.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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	splash10-03di-1009000000-78a39452af06b1f66c1d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-2003900000-7300cb8bf451e3a14f81	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
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0159-0019000000-9d9810e16459120201fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00kr-0942000000-432aa78e495cb764bf6a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-0922000000-8e80b2969083df9af733	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0169000000-7839341ea49cae9ec8cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0922000000-8e80b2969083df9af733	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0279000000-0ee0061b508877e5251c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00kr-0942000000-432aa78e495cb764bf6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-febde21288cfd8b65bba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-5009000000-2bb94673281db9c71250	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9012000000-ebdcd48decdc15ee504a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0089-0009000000-97fc4892888449eada82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gwb-0039000000-0c4c3d30828e5db88fd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9053000000-4d294aabf5e9cb6ea3b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-cba07e04dae1eba32c79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-3085d1f976b6e0a52538	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05tf-3159000000-79cc5ce3bdd0230c2838	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0009000000-8f66bae3e284a8e7f018	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-750db431dd4870d399aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ri-0197000000-0b9db2d8ea5a518c1b83	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
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ophthalmic. Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

Mechanism of Toxicity

The bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

Metabolism

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes

Minimum Risk Level

Not Available

Health Effects

Antibiotic resistance

Symptoms

The most common side effects from antibiotics are diarrhea, nausea, vomiting. Fungal infections of the mouth, digestive tract and vagina can also occur with antibiotics

Treatment

In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID