sodium (2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 154003
• Molecular Formular: C17H19N2NaO6S
• Molecular Mass: 402.39733
• Monoisotopic Mass: 402.08615162
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)c1c(cccc1OC)OC)C(=O)[O-])C.[Na+]
• Canonical SMILES: COc1cccc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)OC.[Na+]
• InChI: InChI=1S/C17H20N2O6S.Na/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4;/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23);/q;+1/p-1/t11-,12+,15-;/m1./s1
• InChIKey: MGFZNWDWOKASQZ-UMLIZJHQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium methicillin(1-)
• Synonyms: Sodium (2,6-dimethoxyphenyl)penicillin; Sodium methicillin; Methicillin sodium salt; (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Azapen; BRL 1241; Belfacillin; Celbenin; Sodium 6-(2',6'-dimethoxybenzamido)penicillanate; Penaureus; Staficyn; Staphcillin; Synticillin; Methicillin Sodium; Methicillin 钠盐

Database IDs

• CAS Number: 132-92-3
• EC Number: 205-083-9
• MDL Number: MFCD07787409
• PubChem SID: 162248142
• PubChem CID: 23667627

CALCULATED PROPERTIES

• Acid pKa: 2.964299
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.7098374
• LogD (pH = 7.4): -2.6935103
• Log P: 0.78517
• Molar Refractivity: 104.2399 cm^3
• Polarizability: 36.30344 Å^3
• Polar Surface Area: 108.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: XH8950000
• 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

Product Information

• Purity: ≥85% (HPLC)
• Salt Data: Na+
• Empirical Formula (Hill Notation): C17H19N2NaO6S
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - 51454

Application
Methicillin is used to study bacterium susceptibility 1, methicillin-resistance in Staphylococcus aureus 2, and to inhibit cell-wall synthesis 3.
Biochem/physiol Actions
Methicillin inhibits cell wall synthesis. In Legionella pneumophila, methicillin causes the formation of membranous lesions through which cytoplasmic contents are lost 3.

Toronto Research Chemicals - M260175

Semi-synthetic antibiotic related to Penicillin. Antimicrobial.

REFERENCES

• Robinson, B., et al.: Biochem. Med. Metab. Biol., 48, 122 (1992)
• Lesnefsky, E., et al.: J. Biol. Chem., 279, 47961 (1992)
• Marroquin, L., et al.: Toxicol. Sci., 97, 539 (1992)