sodium (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-carboxylate

• ChemBase ID: 103129
• Molecular Formular: C19H17ClN3NaO5S
• Molecular Mass: 457.86315
• Monoisotopic Mass: 457.04751362
• SMILES: [Na+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)c3c(onc3c3ccccc3Cl)C)[C@H]2SC1(C)C
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl.[Na+]
• InChI: InChI=1S/C19H18ClN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
• InChIKey: SCLZRKVZRBKZCR-SLINCCQESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (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-carboxylate
• IUPAC Traditional name: sodium cloxacillin(1-)
• Synonyms: Cloxacillin sodium salt; 5-Methyl-3-(o-chlorophenyl)-4-isoxazolyl] pencillin; CLOXACILLIN SODIUM SALT; Sodium Cloxacillin; 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Monosodium Salt; Staphybiotic; (2S,5R,6R)-6-[[[3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Ankerbin; 3-(o-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin Sodium Salt; Austrastaph; BRL 1621 Sodium Salt; Cloxapen; Ekvacillin; Gelstaph; Orbenin; Orbenin Sodium; Prevencilina P; Prostaphilin A; Prostaphlin A; Syntarpen Sodium Salt; Tegopen; Sodium 3-(O-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin

Database IDs

• CAS Number: 642-78-4; 7081-44-9
• EC Number: 211-390-9
• MDL Number: MFCD00063568
• Beilstein Number: 4103180
• PubChem SID: 162102916; 24856654
• PubChem CID: 23675320

CALCULATED PROPERTIES

• Acid pKa: 3.7497845
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.55099535
• LogD (pH = 7.4): -0.9830029
• Log P: 2.3017397
• Molar Refractivity: 117.4742 cm^3
• Polarizability: 41.823692 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• Storage Condition: 2-8°C
• RTECS: XH8750000; XH8920000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Salt Data: Na+
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C19H17ClN3NaO5S
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02150702

Sodium Salt
White micro-crystalline powder
pH 6.0-7.5
Antibacterial

Sigma Aldrich - 27555

Biochem/physiol Actions
Cloxacillin interferes with the last stage of bacterial cell wall synthesis by binding to penicillin-binding proteins. This inhibits the necessary cross-linking and leads to autolysis of the bacteria by autolysins.
Application
Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is used against staphylococci that produce β-lactamase. It is used to study the role of pH in antibiotic effectiveness1 and how oxgall, acid, and hydrogen peroxide stress effects the susceptibility of Bifidobacteria2.

Toronto Research Chemicals - C587460

Cloxacillin is an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lactamase due to its inhibitory effects on beta-lactamase binding.

REFERENCES

• Gibbs, D.L. et al.: Curr. Microbiol., 2, 239 (1979)
• Dmitrova, D. et al.: Farmat., 48, 28 (1979)
• CRaven, N. et al.: Res. Vet. Sci., 29, 57 (1979)