sodium (6R,7S)-3-[(carbamoyloxy)methyl]-7-(2H3)methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163924
• Molecular Formular: C16H16N3NaO7S2
• Molecular Mass: 449.43391
• Monoisotopic Mass: 449.03273615
• SMILES: S1[C@H]2N(C(=C(C1)COC(=O)N)C(=O)[O-])C(=O)[C@]2(NC(=O)Cc1sccc1)OC.[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-(^2H₃)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 (6R,7S)-3-[(carbamoyloxy)methyl]-7-(^2H₃)methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-(methoxy-d3)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Betacef-d3; Cefaxilin-d3 Sodium; Cenomycin-d3; Farmoxin-d3; MK 306-d3; Mefoxin-d3; Mefoxithin-d3; Mefoxitin-d3; Merxin-d3; Serviflox-d3; Cefoxitin-d3 Sodium Salt

Database IDs

• PubChem SID: 162258059
• PubChem CID: 71314614

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

DETAILS

Toronto Research Chemicals - C243202

Labelled Cefoxitin. 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)