Alatrofloxacin

Identification

Summary

Alatrofloxacin is a fluoroquinolone antibiotic used to treat a variety of bacterial infections.

Generic Name

Alatrofloxacin

DrugBank Accession Number

DB09335

Background

Alatrofloxacin is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt. It was withdrawn from the U.S. market in 2001.

Type

Small Molecule

Groups

Approved, Withdrawn

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Alatrofloxacin (DB09335)

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Weight

Average: 558.518
Monoisotopic: 558.183852418

Chemical Formula

C₂₆H₂₅F₃N₆O₅

Synonyms

• Alatrofloxacin

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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Alatrofloxacin mesylate	2IXX802851	157605-25-9	CYETUYYEVKNSHZ-LGOOQLFJSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Trovan I.V.	Liquid	5 mg / mL	Intravenous	Pfizer Canada Ulc	1998-12-23	2001-11-22

Categories

Drug Categories

• Anti-Infective Agents
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• Narrow Therapeutic Index Drugs
• Quinolines
• Quinolones
• Topoisomerase II Inhibitors
• Topoisomerase Inhibitors

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Naphthyridine carboxylic acids and derivatives / Fluoroquinolones / Pyridinecarboxylic acids / Dialkylarylamines / Aminopyridines and derivatives / Fluorobenzenes / Piperidines / Aryl fluorides / Imidolactams / Vinylogous amides / Pyrrolidines / Heteroaromatic compounds / Amino acids / Carboxylic acids / Carboximidic acids / Monocarboxylic acids and derivatives / Azacyclic compounds / Propargyl-type 1,3-dipolar organic compounds / Hydrocarbon derivatives / Monoalkylamines / Organic oxides / Organofluorides / Organooxygen compounds / Organopnictogen compounds

show 14 more

Substituents

Alpha peptide / Amine / Amino acid / Amino acid or derivatives / Aminopyridine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid / Dialkylarylamine / Diazanaphthalene / Fluorobenzene / Fluoroquinolone / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Naphthyridine / Naphthyridine carboxylic acid / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperidine / Primary aliphatic amine / Primary amine / Propargyl-type 1,3-dipolar organic compound / Pyridine / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Pyrrolidine / Vinylogous amide

show 34 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

7QVV6I50DT

CAS number

146961-76-4

InChI Key

UUZPPAMZDFLUHD-VUJLHGSVSA-N

InChI

InChI=1S/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1

IUPAC Name

7-[(1R,5S,6S)-6-[(2S)-2-[(2S)-2-aminopropanamido]propanamido]-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

SMILES

[H][C@@]12CN(C[C@]1([H])[C@H]2NC(=O)[C@H](C)NC(=O)[C@H](C)N)C1=NC2=C(C=C1F)C(=O)C(=CN2C1=CC=C(F)C=C1F)C(O)=O

References

General References

Not Available

External Links

PubChem Compound

3086677

PubChem Substance

310265213

ChemSpider

21243647

RxNav

141440

ChEBI

135829

ChEMBL

CHEMBL1201197

ZINC

ZINC000100067477

Wikipedia

Alatrofloxacin

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Liquid	Intravenous	5 mg / mL

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6080756	No	2000-06-27	2016-07-05
US6194429	No	2001-02-27	2018-07-23

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0388 mg/mL	ALOGPS
logP	0.65	ALOGPS
logP	-0.83	Chemaxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.41	Chemaxon
pKa (Strongest Basic)	8.09	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	9	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	157.96 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	135.64 m3·mol-1	Chemaxon
Polarizability	52.84 Å3	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4l-0000590000-182bd234e60f6100f442
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0100960000-5bf99f18036141a04d6d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05fr-0000930000-57f891b7301ca4684581
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-006x-6000940000-2e129aaf8c60f35061cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0541-0019430000-62b8e782b09c29df829e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014l-0001920000-d4c7214bc8a9eb47c42d

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	231.62674	predicted	DeepCCS 1.0 (2019)
[M+H]+	233.52216	predicted	DeepCCS 1.0 (2019)
[M+Na]+	239.30008	predicted	DeepCCS 1.0 (2019)

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Drug created at November 26, 2015 23:56 / Updated at February 02, 2024 22:53