(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 hydrate sodium

• ChemBase ID: 132650
• Molecular Formular: C19H20ClN3NaO6S
• Molecular Mass: 476.88637
• Monoisotopic Mass: 476.06590334
• SMILES: Cc1c(c(no1)c1ccccc1Cl)C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)O.O.[Na]
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl.O.[Na]
• InChI: InChI=1S/C19H18ClN3O5S.Na.H2O/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);;1H2/t13-,14+,17-;;/m1../s1
• InChIKey: KNNWTOJBVOKDPC-VICXVTCVSA-N

NAMES AND DATABASE IDS

Names

• 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 hydrate sodium
• IUPAC Traditional name: cloxacillin hydrate sodium
• Synonyms: Cloxacillin sodium salt monohydrate; 氯唑西林 钠盐 水合物

Database IDs

• CAS Number: 7081-44-9
• EC Number: 211-390-9
• MDL Number: MFCD00150735
• Beilstein Number: 5403885
• PubChem SID: 24869851; 162226927; 24893156
• PubChem CID: 16213036

CALCULATED PROPERTIES

• Acid pKa: 3.7497845
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.55099535
• LogD (pH = 7.4): -0.9830029
• Log P: 2.3017397
• Molar Refractivity: 106.6371 cm^3
• Polarizability: 41.93821 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: XH8920000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: VETRANAL™, analytical standard
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C19H17ClN3NaO5S · H2O

DETAILS

Sigma Aldrich - C9393

Application
Cloxacillin is a semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. It is also known as cloxacillin sodium. It is used to treat infections caused by penicillin G-resistant staphylococci1. It has been used in studies of topical antibacterial agent for burn and crush wounds2.
Biochem/physiol Actions
Cloxacillin inhibits the last stage of bacterial cell wall synthesis by binding to certain penicillin-binding proteins (PBPs), which results in cell lysis. Cell lysis is mediated by bacterial cell wall autolytic enzymes. Cloxacillin may interfere with autolysin inhibitors. Cloxacillin is used as an AmpC β-lactamase inhibitor in combination with β-lactam antibiotics.
Cloxacillin is used as an AmpC β-lactamase inhibitor in combination with β-lactam antibiotics.

Sigma Aldrich - 46140

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC