ContaminantDB: Trovafloxacin

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:17 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022159

Identification

Common Name

Trovafloxacin

Class

Small Molecule

Description

Trovafloxacin (sold as Trovan by Pfizer) is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was withdrawn from the market due to the risk of hepatotoxicity. It had better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones. [Wikipedia]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
TVFX	HMDB
7-[(1R,5S)-6-Amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate	HMDB
Trovafloxacin	MeSH

Chemical Formula

C₂₀H₁₅F₃N₄O₃

Average Molecular Mass

416.353 g/mol

Monoisotopic Mass

416.110 g/mol

CAS Registry Number

147059-72-1

IUPAC Name

7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Traditional Name

trovafloxacin

SMILES

[H][C@@]12CN(C[C@]1([H])C2N)C1=C(F)C=C2C(=O)C(=CN(C3=C(F)C=C(F)C=C3)C2=N1)C(O)=O

InChI Identifier

InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16?

InChI Key

WVPSKSLAZQPAKQ-SOSAQKQKSA-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
4-aminopiperidine
Aminopyridine
Halobenzene
Fluorobenzene
Aryl fluoride
Piperidine
Aryl halide
Monocyclic benzene moiety
Pyridine
Imidolactam
Benzenoid
Pyrrolidine
Heteroaromatic compound
Vinylogous amide
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organofluoride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.07 g/L	ALOGPS
logP	0.86	ALOGPS
logP	0.14	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.41	ChemAxon
pKa (Strongest Basic)	9.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.04 m³·mol⁻¹	ChemAxon
Polarizability	38.34 Å³	ChemAxon
Number of Rings	5	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	splash10-000b-2119000000-91742a1b93c82cf212d5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7003900000-4818baa2c2a4f74b2220	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0006900000-2710bf3a67a56277c91a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fyk-0009200000-09205f5639aced9d56b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2109000000-c9470417cb99415a7647	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gi0-0009300000-889348bd48600cb6c1a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0019000000-74abce38948c12f68820	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdi-0269000000-576e128582edeb4bb363	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000900000-3867ec761451154ce3c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-73e5733bc87ce9b57a25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v7j-0019000000-0c5ac23c528b63c072a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0008900000-f2e46d3c5f677f467399	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-cecc830cc169437c1861	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0129000000-26a3bdcab7848d604140	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

Not Available

HMDB ID

HMDB0014823

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

Trovafloxacin

Chemspider ID

56670

ChEBI ID

Not Available

PubChem Compound ID

62959

Kegg Compound ID

C07664

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Trovafloxacin (CHEM022159)

Structure for CHEM022159: Trovafloxacin