(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-carboxylic acid

• ChemBase ID: 1165
• Molecular Formular: C16H17N3O7S2
• Molecular Mass: 427.45208
• Monoisotopic Mass: 427.0507919
• SMILES: S1[C@H]2N(C(=O)[C@@]2(OC)NC(=O)Cc2sccc2)C(=C(C1)COC(=O)N)C(=O)O
• Canonical SMILES: CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N
• InChI: InChI=1S/C16H17N3O7S2/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)/t14-,16+/m1/s1
• InChIKey: WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-carboxylic acid
• IUPAC Traditional name: mefoxitin
• Brand Name: Mefoxin; Mefoxitin
• Synonyms: Cefoxitin

Database IDs

• CAS Number: 35607-66-0
• PubChem SID: 46505845; 160964628
• PubChem CID: 441199

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5866818
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.619845
• LogD (pH = 7.4): -3.059385
• Log P: 0.28835905
• Molar Refractivity: 98.7643 cm^3
• Polarizability: 38.30897 Å^3
• Polar Surface Area: 148.26 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.22
• LOG S: -3.34
• Solubility (Water): 1.95e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.02 [SANGSTER (1993)]

DETAILS

DrugBank - DB01331

• Drug Groups: approved
• Description: Cefoxitin is a semi-synthetic, broad-spectrum cepha antibiotic for intravenous administration. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans.
• Indication: For the treatment of serious infections caused by susceptible strains microorganisms.
• Pharmacology: Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria.
• Toxicity: The acute intravenous LD50 in the adult female mouse and rabbit was about 8.0 g/kg and greater than 1.0 g/kg, respectively. The acute intraperitoneal LD50 in the adult rat was greater than 10.0 g/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).
• Half Life: The half-life after an intravenous dose is 41 to 59 minutes.
• Elimination: Approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period, resulting in high urinary concentrations. Cefoxitin passes into pleural and joint fluids and is detectable in antibacterial concentrations in bile.
• External Links: Wikipedia; RxList; Drugs.com