norfloxacin   Click here for help

GtoPdb Ligand ID: 12408

Synonyms: AM-715 | Chibroxin® | MK-0366 | Noroxin®
Approved drug
norfloxacin is an approved drug (FDA (1986), EMA)
Compound class: Synthetic organic
Comment: Norfloxacin is a fluoroquinolone compound with broad-spectrum antibacterial activity [3].
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 319.33
XLogP 1.69
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)N3CCNCC3)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O
InChI InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChI Key OGJPXUAPXNRGGI-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Norfloxacin has approval from the US FDA with a 'Boxed Warning' to highlight the risk of serious adverse reactions. An oral formulation (Noroxin®) and an ophthalmic solution (Chibroxin®) were marketed in the US by Merck but are now discontinued. The drug has EMA approval and is marketed in a number of European countries, however the EMA has issued restrictive guidelines on the use of fluoroquinolone containing medicines [2]. In 2008, the EMA withdrew authorisation for the use of oral formulations of norfloxacin to treat complicated pyelonephritis [1]. Other national approval agencies may have granted marketing authorisation. See Drugs.com's International Drug Names list for further information.
External links Click here for help
For extended ADME data see the following:

Drugs.com