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Identification
NameFlucloxacillin
Accession NumberDB00301  (APRD00609)
TypeSmall Molecule
GroupsApproved
DescriptionAntibiotic analog of cloxacillin.
Structure
Thumb
Synonyms
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin
Floxacillin
Floxapen
Flucloxacilina
Flucloxacillin
Flucloxacilline
Flucloxacillinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluclox 250liquid250 mgoralAyerst Laboratories1981-12-311997-08-15Canada
Fluclox 250 Cap 250mgcapsule250 mgoralAyerst Laboratories1981-12-311997-08-15Canada
Fluclox 500 Cap 500mgcapsule500 mgoralAyerst Laboratories1981-12-311997-08-15Canada
Fluclox-125 Pws 125mg/5mlpowder for solution125 mgoralWyeth Ayerst Canada Inc.1995-12-311997-01-14Canada
Fluclox-250 Cap 250mgcapsule250 mgoralWyeth Ayerst Canada Inc.1995-12-311997-08-14Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FlopenAspen
FloxapenGSK
FlucloxACI
SesamolNot Available
SoftapenNot Available
StaphylexActavis
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Flucloxacillin sodium
34214-51-2
Thumb
  • InChI Key: PARMJFIQRZRMHG-VICXVTCVSA-M
  • Monoisotopic Mass: 493.0486566
  • Average Mass: 493.869
DBSALT000345
Categories
UNII43B2M34G2V
CAS number5250-39-5
WeightAverage: 453.872
Monoisotopic: 453.056147271
Chemical FormulaC19H17ClFN3O5S
InChI KeyInChIKey=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
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)[[email protected]]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Aryl chloride
  • Heteroaromatic compound
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Oxazole
  • Isoxazole
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Oxacycle
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat bacterial infection by susceptible microorganisms.
PharmacodynamicsFlucloxacillin 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 actionBy 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.
Related Articles
AbsorptionBioavailability is 50–70% following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life0.75–1 hour
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier-0.9862
Caco-2 permeable-0.8734
P-glycoprotein substrateNon-substrate0.6184
P-glycoprotein inhibitor INon-inhibitor0.8765
P-glycoprotein inhibitor IINon-inhibitor0.9438
Renal organic cation transporterNon-inhibitor0.965
CYP450 2C9 substrateNon-substrate0.8279
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6012
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.926
Ames testNon AMES toxic0.6791
CarcinogenicityCarcinogens 0.5695
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.0834 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9997
hERG inhibition (predictor II)Non-inhibitor0.8323
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Liquidoral250 mg
Capsuleoral500 mg
Powder for solutionoral125 mg
Capsuleoral250 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.58SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0545 mg/mLALOGPS
logP2.69ALOGPS
logP2.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.85 m3·mol-1ChemAxon
Polarizability41.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Nayler, J.H.C.; U.S. Patent 3.239307; March 8,1966; assigned to Beecharn Group Limited, England.

General ReferencesNot Available
External Links
ATC CodesJ01CF05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolFlucloxacillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Flucloxacillin.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Flucloxacillin.
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Flucloxacillin.
DicoumarolFlucloxacillin may increase the anticoagulant activities of Dicoumarol.
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Flucloxacillin.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Flucloxacillin.
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Flucloxacillin.
Ethyl biscoumacetateFlucloxacillin may increase the anticoagulant activities of Ethyl biscoumacetate.
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Flucloxacillin.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Flucloxacillin.
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Flucloxacillin.
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Flucloxacillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Flucloxacillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Flucloxacillin.
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Flucloxacillin.
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Flucloxacillin resulting in a loss in efficacy.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Flucloxacillin.
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Flucloxacillin.
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Flucloxacillin.
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Flucloxacillin.
PhenindioneFlucloxacillin may increase the anticoagulant activities of Phenindione.
PhenprocoumonFlucloxacillin may increase the anticoagulant activities of Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Flucloxacillin.
PiperacillinThe serum concentration of Flucloxacillin can be increased when it is combined with Piperacillin.
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Flucloxacillin.
ProbenecidThe serum concentration of Flucloxacillin can be increased when it is combined with Probenecid.
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Flucloxacillin.
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Flucloxacillin.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Flucloxacillin.
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Flucloxacillin.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Flucloxacillin.
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Flucloxacillin.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Flucloxacillin.
WarfarinFlucloxacillin may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take on an empty stomach.

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
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:17139284 ]
  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:17016423 ]
  3. Lacey RW: Mechanisms of resistance to beta-lactam antibiotics in Staphylococcus aureus. Scand J Infect Dis Suppl. 1984;42:64-71. [PubMed:6335600 ]
  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. doi: 10.1111/j.1574-6976.2007.00097.x. Epub 2008 Feb 11. [PubMed:18266857 ]
  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:318800 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 19, 2016 10:44