Cloxacillin (CED0003254)

Record Information
Version1.0
Creation Date2016-05-25 18:25:28 UTC
Update Date2026-08-20 02:26:10 UTC
Accession NumberCHEM022246
Identification
Common NameCloxacillin
ClassSmall Molecule
Description
Cloxacillin is an organic compound with the chemical formula C19H18ClN3O5S and an average molecular weight of 435.88 g/mol. Cloxacillin 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 three protein targets: Penicillin-binding protein 1A (pbpA), Penicillin-binding protein 2X (pbpX), and D-alanyl-D-alanine carboxypeptidase DacA (dacA). It is used within the healthcare, pharmaceuticals, and veterinary sectors as an antibiotic and part of the penicillins. Exposure to the substance occurs through oral, intravenous, intramuscular, and inhalation routes. Cloxacillin has been found in or released from 16 recorded sources. These include drinking water and water supply sources such as drinking water. Within food, food processing, and cookware, it is associated with processing meats, food preservation, and agglomerated sugar products. Household cleaning and consumer product sources include soap detergents, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and tobacco smoke filters. Additionally, it is found in electrical and electronic equipment, specifically within television systems, video games, hybrid capacitors, antennas, and electrically stimulated smoking devices.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
(3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillinChEBI
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acidChEBI
CloxacilinaChEBI
CloxacillineChEBI
CloxacillinumChEBI
MCIPCKegg
OrbeninKegg
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanateGenerator
Cloxacillin sodiumHMDB
ChloroxacillinHMDB
TegopenHMDB
Cloxacillin, sodiumHMDB
SyntarpenHMDB
Sodium, cloxacillinHMDB
Sodium cloxacillinHMDB
Chemical FormulaC19H18ClN3O5S
Average Molecular Mass435.881 g/mol
Monoisotopic Mass435.066 g/mol
CAS Registry Number61-72-3
IUPAC Name(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namecloxacillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O
InChI IdentifierInChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
InChI KeyLQOLIRLGBULYKD-JKIFEVAISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Penam
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Beta-lactam
  • Isoxazole
  • Lactam
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.053 g/LALOGPS
logP2.61ALOGPS
logP2.3ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.64 m³·mol⁻¹ChemAxon
Polarizability41.64 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-9442300000-e216b172b6089bc0b628Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9201100000-8c62d7bf4821412834e5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-0980100000-1acb1c4e617b9afd066cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-0980100000-1acb1c4e617b9afd066cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-0980100000-1acb1c4e617b9afd066cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a5a-0560910000-05dcf2cead0bc1f49482Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-1900000000-a2a9637ec3640b22d439Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03g0-1981500000-b5aa89e8243c95661294Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03mi-1980000000-5959a8cd3ff0d7b69e86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0900-4940000000-4f39d56cd5b7d76c29f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0092000000-f42335fd75afb22d0d5bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0795000000-0f4a7aa6aa6b6709cf76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2920000000-e0da457c632e3e5d44daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1051900000-02e2b7b8281ef5861490Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9250100000-ed86f55f0155aa43591cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001m-9632000000-a8ea4618ee5a92c98b3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0110900000-7f26bb1ece4516994fc6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-022i-0590300000-7f87c7e79e0101a13c0dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-1950000000-43f0f287563f32d24bb4Not 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
6211.0Log mg/kg[3500:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, 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 structureNucleoproteinP15682Influenza A virus (strain A/Wilson-Smith/1933 H1N1)Predicted (SEA)0.233548
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)63.9142
Click to view 3D structureG-protein coupled bile acid receptor 1Q80T02Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)356.082
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)84.7778
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)176.406
Click to view 3D structureHexokinase HKDC1Q2TB90HumansPredicted (SEA)75.9808
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)4236.87
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3888.02
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)3694.72
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)3333.89
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)5.60514
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)3241.17
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)10.7432
Click to view 3D structureC-terminal processing protease of the D1 proteinQ36792Spinacia oleraceaPredicted (SEA)23.5883
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)720.884
Click to view 3D structurePhenylalanine--tRNA ligase alpha subunitQ8P1K1Streptococcus pyogenes serotype M18 (strain MGAS8232)Predicted (SEA)4.82665
E3 ubiquitin-protein ligase SMURF2 structureClick to view 3D structureE3 ubiquitin-protein ligase SMURF2Q9HAU4HumansPredicted (SEA)34.5651
Leukemia inhibitory factor receptor structureClick to view 3D structureLeukemia inhibitory factor receptorP42702HumansPredicted (SEA)61.1116
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)541.675
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5780.46
Neuropeptide Y receptor type 1 structureClick to view 3D structureNeuropeptide Y receptor type 1P25929HumansPredicted (SEA)408.241
Concentrations
Not Available
External Links
DrugBank IDDB01147
HMDB IDHMDB0015278
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCloxacillin
Chemspider ID5873
ChEBI ID49566
PubChem Compound ID6098
Kegg Compound IDC06923
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16540070
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16853954
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24858821
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25305230
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25582344
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26365730
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27446834
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27889744
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7417768
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8566082