Gemifloxacin (CED0007151)

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:37 UTC

Update Date

2026-05-14 16:58:17 UTC

Accession Number

CHEM022251

Identification

Common Name

Gemifloxacin

Class

Small Molecule

Description

Gemifloxacin is an organic compound with the chemical formula C18H20FN5O4 and an average molecular weight of 389.38 g/mol. Gemifloxacin belongs to the naphthyridines, a subclass of diazanaphthalenes within the organic compounds. It is further categorized as an organoheterocyclic compound. The compound is found in or released from two recorded sources: pharmaceuticals & veterinary products, specifically antibiotics and quinolone antibacterials, as well as healthcare. Recorded exposure routes for the substance include oral and inhalation. Gemifloxacin acts as an inhibitor or modulator of three recorded protein targets: DNA gyrase subunit B (gyrB), DNA topoisomerase 4 subunit A (parC), and DNA gyrase subunit A (gyrA).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Factiv	Kegg
Gemifloxacin mesilate	HMDB
Gemifloxacin mesylate	HMDB
7-(3-Aminomethyl-4-methoxyimino-pyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-(1,8)-naphthyridine-3-carboxylic acid	HMDB
Factive	HMDB

Chemical Formula

C₁₈H₂₀FN₅O₄

Average Molecular Mass

389.381 g/mol

Monoisotopic Mass

389.150 g/mol

CAS Registry Number

175463-14-6

IUPAC Name

7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Traditional Name

gemifloxacin

SMILES

CO\N=C1/CN(CC1CN)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O

InChI Identifier

InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+

InChI Key

ZRCVYEYHRGVLOC-HYARGMPZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridine carboxylic acids and derivatives

Alternative Parents

Substituents

Naphthyridine carboxylic acid
Fluoroquinolone
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Dialkylarylamine
Aminopyridine
Imidolactam
Pyridine
Aryl fluoride
Aryl halide
Heteroaromatic compound
Vinylogous amide
Pyrrolidine
Amino acid
Amino acid or derivatives
Oxime ether
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organohalogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organofluoride
Organonitrogen compound
Organooxygen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:101853 )
1,8-naphthyridine derivative (CHEBI:101853 )
quinolone antibiotic (CHEBI:101853 )
fluoroquinolone antibiotic (CHEBI:101853 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	0.21 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.92	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	5.53	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	121.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.74 m³·mol⁻¹	ChemAxon
Polarizability	39.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-7009000000-6c1e062d9b76f111f18c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00dj-5202900000-fac5d6018c989a382d60	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-0009000000-216eb233a8cd0c046a00	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0096-0109000000-01212fa7e1d9f9ed8c9b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01qi-9301000000-91707fbf708434bd2935	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-0009000000-1a9cdceacdbdcde5efa9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03xu-0019000000-998e1aa5045a6e80b457	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ik9-0229000000-77756438384a40006769	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-0009000000-7c9ea1e02153230b8e99	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-ebc17fb139bdaa964784	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0hh9-0019000000-6a271d23da85cc6a804f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-4ae393c96b503585c9e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-0009000000-eb07db8d835c2d5bcfc9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-1059000000-ca44826b3169690b8ff4	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2130.0	Log mg/kg	[1200:3800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
345	Quinolone antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Gemifloxacin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	DNA topoisomerase 4 subunit A	P0C1U9	Staphylococcus aureus	Predicted (SEA)	0.233548
Click to view 3D structure	Dipeptidyl peptidase 4	P27487	Humans	Predicted (SEA)	29.1156
Click to view 3D structure	DNA gyrase subunit A	P9WG47	Mycobacterium tuberculosis	Predicted (SEA)	1.16774
Click to view 3D structure	Dual specificity protein kinase CLK2	P49760	Humans	Predicted (SEA)	1038.28
Click to view 3D structure	Serine/threonine-protein kinase D3	O94806	Humans	Predicted (SEA)	957.701
Click to view 3D structure	Dual specificity protein kinase CLK4	Q9HAZ1	Humans	Predicted (SEA)	1034.38
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	449.891
Click to view 3D structure	V-type proton ATPase subunit B, brain isoform	P21281	Humans	Predicted (SEA)	2.02408
Click to view 3D structure	MAP kinase-activated protein kinase 3	Q16644	Humans	Predicted (SEA)	1098.45
Click to view 3D structure	Isocitrate lyase	P9WKK7	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	4.35956
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q13627	Humans	Predicted (SEA)	1746.7
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	1916.49
Click to view 3D structure	Ribosomal protein S6 kinase beta-1	P23443	Humans	Predicted (SEA)	1359.64
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	1959.93
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	2523.64
Click to view 3D structure	Serine/threonine-protein kinase Chk1	O14757	Humans	Predicted (SEA)	1752.31
Click to view 3D structure	Serine/threonine-protein kinase PLK1	P53350	Humans	Predicted (SEA)	1586.57
Click to view 3D structure	RAC-gamma serine/threonine-protein kinase	Q9Y243	Humans	Predicted (SEA)	1447.84
Click to view 3D structure	cAMP-dependent protein kinase catalytic subunit alpha	P17612	Humans	Predicted (SEA)	1790.3
Click to view 3D structure	Glycogen synthase kinase-3 alpha	P49840	Humans	Predicted (SEA)	1932.45
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	1975.81
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	2162.26
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	2011.0
Click to view 3D structure	Protein kinase C delta type	Q05655	Humans	Predicted (SEA)	1606.96
Click to view 3D structure	RAC-alpha serine/threonine-protein kinase	P31749	Humans	Predicted (SEA)	1878.42