sodium (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 130739
• Molecular Formular: C16H16N3NaO7S2
• Molecular Mass: 449.43391
• Monoisotopic Mass: 449.03273615
• SMILES: CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)[O-])NC(=O)Cc1cccs1.[Na+]
• Canonical SMILES: CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])COC(=O)N.[Na+]
• InChI: InChI=1S/C16H17N3O7S2.Na/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19;/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22);/q;+1/p-1/t14-,16+;/m1./s1
• InChIKey: GNWUOVJNSFPWDD-XMZRARIVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium cefoxitin(1-)
• Synonyms: Cefoxitin sodium salt; (6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Betacef; Cefaxilin Sodium; Cenomycin; Farmoxin; MK 306; Mefoxin; Mefoxithin; Mefoxitin; Merxin; Serviflox; Cefoxitin Sodium Salt; 头孢西丁 钠盐

Database IDs

• CAS Number: 33564-30-6
• EC Number: 251-574-6
• MDL Number: MFCD00079042
• PubChem SID: 162225017; 24892725
• PubChem CID: 23667300

CALCULATED PROPERTIES

• Acid pKa: 3.5866818
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.619845
• LogD (pH = 7.4): -3.059385
• Log P: 0.28835905
• Molar Refractivity: 109.6014 cm^3
• Polarizability: 38.192413 Å^3
• Polar Surface Area: 151.09 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: >160°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: XI0330500
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: analytical standard, for drug analysis
• Shelf Life: (limited shelf life, expiry date on the label)

DETAILS

Toronto Research Chemicals - C243200

Semi-synthetic antibiotic derived from Cephamycin C, possessing high resistance to β-lactamase inactivation. An antibacterial.

REFERENCES

• Wallick, H., et al.: Antimicrob. Agents Chemother., 5, 25 (1974)
• Brenner, G.S., et al.: Anal. Profiles Drug Subs., 11, 169 (1974)