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Identification
Name Flucloxacillin
Accession Number DB00301 (APRD00609)
Type small molecule
Groups approved
Description

Antibiotic analog of cloxacillin. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Floxacillin
  • Flucloxacilina [INN-Spanish]
  • Flucloxacillin Sodium
  • Flucloxacillin-Sodium
  • Flucloxacilline [INN-French]
  • Flucloxacillinum [INN-Latin]
Brand names
  • Floxapen
  • Fluclox
  • Sesamol
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 5250-39-5
Weight Average: 453.872
Monoisotopic: 453.056147271
Chemical Formula C19H17ClFN3O5S
InChI Key InChIKey=UIOFUWFRIANQPC-JKIFEVAISA-N
InChI
InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
Plain Text
IUPAC Name
(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1F)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes
  • Phenylpropenes
  • Penicillins
  • Cinnamaldehydes
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Phenylpropenes
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Isoxazoles
  • Aryl Halides
  • Carboxylic Acids and Derivatives
  • Halobenzenes
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Cinnamaldehydes
  • Carboxamides and Derivatives
  • Oxazoles
  • Lactams
  • Imines
  • Azetidines
  • Thiazolidines
Pharmacology
Indication Used to treat bacterial infection by susceptible microorganisms.
Pharmacodynamics Flucloxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Flucloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Flucloxacillin results from the inhibition of cell wall synthesis and is mediated through flucloxacillin binding to penicillin binding proteins (PBPs). Flucloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Mechanism of action By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, flucloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that flucloxacillin interferes with an autolysin inhibitor.
Absorption Bioavailability is 50–70% following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic.
Route of elimination Not Available
Half life 0.75–1 hour
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3.2 PhysProp
Predicted Properties
Property Value Source
water solubility 5.45e-02 g/l ALOGPS
logP 2.69 ALOGPS
logP 2.44 ChemAxon Molconvert
logS -3.92 ALOGPS
pKa 13.64 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 112.74 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 106.85 ChemAxon Molconvert
polarizability 41.69 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D04196 Link_out
KEGG Compound C11748 Link_out
PubChem Compound 21319 Link_out
PubChem Substance 46508276 Link_out
ChemSpider 20037 Link_out
ChEBI 5098 Link_out
ChEMBL 5098 Link_out
Therapeutic Targets Database DAP001163 Link_out
PharmGKB PA10266 Link_out
Drug Product Database 525561 Link_out
Wikipedia http://en.wikipedia.org/wiki/Flucloxacillin Link_out
ATC Codes
  • J01CF05
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take on an empty stomach.
Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Lacey RW: Mechanisms of resistance to beta-lactam antibiotics in Staphylococcus aureus. Scand J Infect Dis Suppl. 1984;42:64-71. Pubmed
  4. Mainardi JL, Villet R, Bugg TD, Mayer C, Arthur M: Evolution of peptidoglycan biosynthesis under the selective pressure of antibiotics in Gram-positive bacteria. FEMS Microbiol Rev. 2008 Mar;32(2):386-408. Epub 2008 Feb 11. Pubmed
  5. Barza M: Antimicrobial spectrum, pharmacology and therapeutic use of antibiotics. Part 2: penicillins. Am J Hosp Pharm. 1977 Jan;34(1):57-67. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.