Cefoxitin
Cefoxitin
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Cefoxitin

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Catalog Number PR35607660
CAS 35607-66-0
Structure
Description Cefoxitin is a semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase. It has a role as an antibacterial drug
Synonyms Mefoxin; CEPHOXITIN; Cefoxitina; Cefoxitine
IUPAC Name (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Weight 427.5
Molecular Formula C16H17N3O7S2
InChI WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
InChI Key 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
Associated Therapies Antibiotic pre-surgical prophylaxis
Drug Categories Amides; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; beta-Lactams; Cephalosporins; Cephamycins; Heterocyclic Compounds, Fused-Ring; Lactams; Nephrotoxic agents; Second-Generation Cephalosporins; Sulfur Compounds; Thiazines
Drug Interactions Abacavir-Cefoxitin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab-The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefoxitin.
Aceclofenac-The risk or severity of nephrotoxicity can be increased when Cefoxitin is combined with Aceclofenac.
Acemetacin-The risk or severity of nephrotoxicity can be increased when Cefoxitin is combined with Acemetacin.
Acenocoumarol-The risk or severity of bleeding can be increased when Cefoxitin is combined with Acenocoumarol.
Half-Life The half-life after an intravenous dose is 41 to 59 minutes.
Isomeric SMILES CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
Type Small Molecule
Therapeutic Category Antibacterials
Pharmacology

Indications

Cefoxitin is utilized for treating serious infections caused by susceptible strains of microorganisms. It is particularly effective against a variety of bacteria that pose significant health risks, providing a targeted approach to managing bacterial infections.

Pharmacodynamics

As a cephamycin antibiotic, Cefoxitin is often grouped with second-generation cephalosporins. It exhibits activity against a broad spectrum of gram-negative bacteria, including anaerobes. A notable feature of Cefoxitin is the presence of a methoxy group at the 7a position, which confers exceptional stability against beta-lactamases, including both penicillinases and cephalosporinases, inherent to gram-negative bacteria.

Metabolism

Cefoxitin undergoes minimal metabolic transformation. Approximately 85 percent of the drug is excreted unchanged by the kidneys within a six-hour timeframe, indicating its predominantly renal elimination pathway.

Mechanism of Action

Cefoxitin exhibits its bactericidal effect through the inhibition of bacterial cell wall synthesis. This mechanism disrupts the structural integrity of the cell wall, ultimately leading to the elimination of the bacterial cells. The interruption in the synthesis process prevents proper cell wall formation, rendering the bacteria unable to sustain their cellular architecture and survive.

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