lomefloxacin   Click here for help

GtoPdb Ligand ID: 12407

Synonyms: Maxaquin® | NY-198 | SC-47111 | Uniquin®
Approved drug
lomefloxacin is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Lomefloxacin is a fluoroquinolone antibacterial compound with activity against both Gram-negative and Gram-positive bacteria [2].
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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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 CDK toolkit. 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 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 72.88
Molecular weight 351.35
XLogP 2.26
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCN1C=C(C(=O)C2=C1C(=C(C(=C2)F)N3CCNC(C)C3)F)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=CC(=C(C(=C21)F)N3CCNC(C3)C)F)C(=O)O
InChI InChI=1S/C17H19F2N3O3/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25)
InChI Key ZEKZLJVOYLTDKK-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Lomefloxacin hydrochloride has approval from the US FDA with a 'Boxed Warning' to highlight the risk of serious adverse reactions. It is indicated for the treatment of infections caused by susceptible strains of bacteria, including acute bacterial exacerbation of chronic bronchitis and urinary tract infections, only when no other treatment options are available. An oral formulation was marketed in the US (under the trade name Maxaquin®) but has since been discontinued. The drug is marketed in Italy, under the trade name Uniquin®, however the EMA has issued restrictive guidelines on the use of fluoroquinolone containing medicines [1].
External links Click here for help
For extended ADME data see the following:

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