Flucloxacillin (CED0003617)

Record Information
Version1.0
Creation Date2016-05-25 18:19:34 UTC
Update Date2026-08-20 02:13:00 UTC
Accession NumberCHEM022085
Identification
Common NameFlucloxacillin
ClassSmall Molecule
Description
Flucloxacillin is an organic compound with the formula C19H17ClFN3O5S and an average molecular weight of 453.87 g/mol. Flucloxacillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The compound is identified as an inhibitor of the protein target penicillin-binding protein 1A (pbpA). It is found in or released from 14 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics and penicillins. It is also linked to food and cookware sources, specifically the processing of meats and fermentation processes for beer. Environmental and consumer sources include drinking water and water supply, as well as household cleaning and consumer products such as bleaching agents, tobacco smoke filters, and non electric simulated smoking devices. Furthermore, it is recorded in electrical and electronic equipment, including antennas, television systems, fixed capacitors and their manufacture, electrically stimulated smoking devices, and electric hearing aids. Recorded exposure routes for the compound include oral and inhalation.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(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 acidChEBI
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillinChEBI
FloxacillinChEBI
FloxapenChEBI
FlucloxacilinaChEBI
FlucloxacillineChEBI
FlucloxacillinumChEBI
MFIPCKegg
(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-carboxylateGenerator
Flucloxacillin-sodiumHMDB
FluorochloroxacillinHMDB
Chemical FormulaC19H17ClFN3O5S
Average Molecular Mass453.872 g/mol
Monoisotopic Mass453.056 g/mol
CAS Registry Number5250-39-5
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
Traditional Nameflucloxacillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O
InChI IdentifierInChI=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
InChI KeyUIOFUWFRIANQPC-JKIFEVAISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as mitomycins. These are polycyclic compounds with a structure based on an aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolequinones
Direct ParentMitomycins
Alternative Parents
Substituents
  • Mitomycin
  • Indole
  • Quinone
  • Pyrrolizine
  • 1,4-diazinane
  • Piperazine
  • Pyrrolidine
  • Vinylogous amide
  • Pyrroline
  • Ketone
  • Aziridine
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Azacycle
  • Secondary amine
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.85 m³·mol⁻¹ChemAxon
Polarizability41.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-9342300000-7f180b75f0b193e6a2bfNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9101010000-2499cba418eeed4ea1e4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ika-1980600000-c09913017680462d6167Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-1890100000-189280e6a5ebaeff7bcbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0900-3930000000-082278659456539aa269Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0029100000-f63d442cb388e6e6a1feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0179100000-cc81474beec5e49ab711Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2943000000-01ada58e630c1108bd3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0110900000-0d61735c2eb814141c04Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2i-0590300000-b1e7d7edf8865b92c33aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01p9-2590000000-21280c81506029576bdbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0030900000-0ee6d1f66c3759d652feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-4190100000-fc1930da2cf7aa599457Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9170000000-0fa52b5f4e2c50ce52adNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6840.0Log mg/kg[3800:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.0778492
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.0778492
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)95.9881
Click to view 3D structureNucleoproteinP15682Influenza A virus (strain A/Wilson-Smith/1933 H1N1)Predicted (SEA)2.95827
Click to view 3D structureC-terminal processing protease of the D1 proteinQ36792Spinacia oleraceaPredicted (SEA)7.23998
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)74.7353
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3090.07
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)210.504
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3890.59
17-beta-hydroxysteroid dehydrogenase 13 structureClick to view 3D structure17-beta-hydroxysteroid dehydrogenase 13Q7Z5P4HumansPredicted (SEA)20.3965
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)261.34
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)181.856
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)126.583
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)76.3701
Vitamin D3 receptor structureClick to view 3D structureVitamin D3 receptorP11473HumansPredicted (SEA)133.589
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)2540.22
Retinoic acid receptor gamma structureClick to view 3D structureRetinoic acid receptor gammaP13631HumansPredicted (SEA)90.2272
Retinoic acid receptor alpha structureClick to view 3D structureRetinoic acid receptor alphaP10276HumansPredicted (SEA)111.48
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)924.537
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)536.303
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)427.548
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)707.338
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)4936.96
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)326.967
Concentrations
Not Available
External Links
DrugBank IDDB00301
HMDB IDHMDB0014446
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlucloxacillin
Chemspider ID20037
ChEBI ID5098
PubChem Compound ID21319
Kegg Compound IDC11748
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15773973
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23032409
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23542420
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25998949
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=5481218