sodium (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate

• ChemBase ID: 72771
• Molecular Formular: C19H20N3NaO6S
• Molecular Mass: 441.43337
• Monoisotopic Mass: 441.09705066
• SMILES: o1c(c(c(n1)c1ccccc1)C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-])C.[Na+].O
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1.O.[Na+]
• InChI: InChI=1S/C19H19N3O5S.Na.H2O/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22;;/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
• InChIKey: ZVIYWUUZWWBNMB-VICXVTCVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
• IUPAC Traditional name: sodium oxacillin(1-) hydrate
• Synonyms: (2S,5R,6R)-3,3-Dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt Hydrate; Penicillin P-12 Hydrate; Sodium Oxacillin Hydrate; BRL-1400 Hydrate; Bactocill Hydrate; Bristopen Hydrate; Stapenor Hydrate; Oxacillin Sodium Salt Monohydrate; Oxacillin sodium monohydrate; Oxacillin sodium salt monohydrate; 苯唑西林 钠盐 一水合物

Database IDs

• CAS Number: 7240-38-21; 7240-38-2
• EC Number: 214-636-3
• MDL Number: MFCD00167146
• Beilstein Number: 4287093
• PubChem SID: 162037692; 24897869; 24870315
• PubChem CID: 23694213

CALCULATED PROPERTIES

• Acid pKa: 3.7509665
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.05194399
• LogD (pH = 7.4): -1.5865542
• Log P: 1.697695
• Molar Refractivity: 112.6694 cm^3
• Polarizability: 39.886116 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >179°°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37
• 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
• Linear Formula: C19H18N3O5SNa · H2O

DETAILS

Selleck Chemicals - S2563

Research Area: Infection
Biological Activity:
Oxacillin sodium monohydrate is an antibacterial agent and is a narrow spectrum beta-lactam antibiotic of the penicillin class. Oxacillin sodium monohydrate is a penicillinase-resistant β-lactam. Oxacillin sodium monohydrate is similar to methicillin, and has replaced methicillin in clinical use. [1][2]

Sigma Aldrich - 46589

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

Toronto Research Chemicals - O758500

Semi-synthetic antibiotic related to Penicillin. Antibacterial.

REFERENCES

• Keefe TJ et al. Acta Chir Plast. 1973;15(1):904 passim.
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)