gatifloxacin   Click here for help

GtoPdb Ligand ID: 10816

Synonyms: AM-1155 | AM1155 | Gatiflo® | GTFX | Tequin® | Zymar®
Approved drug
gatifloxacin is an approved drug
Compound class: Synthetic organic
Comment: Gatifloxacin is a synthetic fourth-generation fluoroquinolone antibacterial with broad-spectrum activity against Gram-negative and Gram-positive pathogens.

gatifloxacin is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 83.8
Molecular weight 375.16
XLogP 4.21
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1c(N2CCNC(C2)C)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
Isomeric SMILES COc1c(N2CCNC(C2)C)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
Withdrawn drug? Yes
IUPAC Name Click here for help
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7423 gatifloxacin
Synonyms Click here for help
AM-1155 | AM1155 | Gatiflo® | GTFX | Tequin® | Zymar®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Gatifloxacin
Other databases
CAS Registry No. 112811-59-3 (source: WHO INN record)
DrugCentral Ligand 1280
GtoPdb PubChem SID 405560257
PubChem CID 5379
Search Google for chemical match using the InChIKey XUBOMFCQGDBHNK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XUBOMFCQGDBHNK
Search PubMed clinical trials gatifloxacin
Search PubMed titles gatifloxacin
Search PubMed titles/abstracts gatifloxacin
UniChem Compound Search for chemical match using the InChIKey XUBOMFCQGDBHNK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XUBOMFCQGDBHNK-UHFFFAOYSA-N

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MedChemExpress
Gatifloxacin (links to external site)
Cat. No. HY-10581