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Alatrofloxacin mesylate

PubChem CID
5282517
Structure
Alatrofloxacin mesylate_small.png
Alatrofloxacin mesylate_3D_Structure.png
Molecular Formula
Synonyms
  • Alatrofloxacin mesylate
  • 146961-77-5
  • 157605-25-9
  • Trovan IV
  • Alatrofloxacin mesylate [USAN]
Molecular Weight
654.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-10-11
  • Modify:
    2025-01-04
Description
ALATROFLOXACIN MESYLATE is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1997 and is indicated for bacterial disease. It was withdrawn in at least one region.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Alatrofloxacin mesylate.png

1.2 3D Conformer

3D Conformer of Parent

2 Biologic Description

SVG Image
SVG Image
Sequence
AA

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

7-[(1S,5R)-6-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl]amino]-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;methanesulfonic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C26H25F3N6O5.CH4O3S/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;1-5(2,3)4/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40);1H3,(H,2,3,4)/t10-,11-,14-,15+,20?;/m0./s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

CYETUYYEVKNSHZ-RSUMCGCKSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C[C@@H](C(=O)N[C@@H](C)C(=O)NC1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N.CS(=O)(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C27H29F3N6O8S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

146961-77-5

3.3.2 Deprecated CAS

157605-25-9

3.3.3 UNII

3.3.4 ChEMBL ID

3.3.5 DSSTox Substance ID

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • alatrofloxacin
  • alatrofloxacin mesylate
  • CP 116,517
  • CP 116517
  • CP-116,517
  • CP-116517
  • Trovan

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
654.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
654.17196756 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
654.17196756 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
221Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
45
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1180
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Anti-Infective Agents
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)
Topoisomerase II Inhibitors
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

9 Toxicity

9.1 Toxicological Information

9.1.1 Drug Induced Liver Injury

Compound
alatrofloxacin mesylate
DILI Annotation
Most-DILI-Concern
Severity Grade
8
Label Section
Withdrawn
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 KEGG: Drug Groups

14.4 KEGG : Antimicrobials

14.5 ChemIDplus

14.6 EPA DSSTox Classification

14.7 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  7. Therapeutic Target Database (TTD)
  8. Springer Nature
  9. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  10. PubChem
  11. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  12. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  13. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  15. PATENTSCOPE (WIPO)
CONTENTS