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Cefoxitin

Cefoxitin structure

CAS No:
35607-66-0
Formula:
C16H17N3O7S2
Chemical Name:
Cefoxitin
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-,(6R,7S)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R-cis)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R,7S)-;(6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefoxitin;Cephoxitin;39951-67-2
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Solid

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. It is a cephalosporin, a semisynthetic derivative, a beta-lactam antibiotic allergen and a cephamycin. It is a conjugate acid of a cefoxitin(1-).|Cefoxitin is a semi-synthetic, broad-spectrum cepha antibiotic for intravenous administration. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans.|Cefoxitin is a Cephalosporin Antibacterial.|Cefoxitin is a semisynthetic, broad-spectrum, second-generation cephalosporin with antibacterial activity. Cefoxitin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.|A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

Cefoxitin Basic Attributes

Molecular Weight：

427.45

Exact Mass：

427.45

EC Number：

252-641-2

UNII：

6OEV9DX57Y

DSSTox ID：

DTXSID1022764

NCI Thesaurus Code：

C61665

ATC Code：

J - Antiinfectives for systemic use

HScode：

2934999090

Characteristics

PSA：

202

XLogP3：

-0.02

Appearance：

White to off-white crystalline powder

Density：

1.6±0.1 g/cm3

Melting Point：

149-150 °C

Boiling Point：

843℃

Flash Point：

>110°(230°F)

Refractive Index：

1.693

Water Solubility：

Predicted solubility in water is less than 0.2mg/ml

Toxicity：

Intravenous-rat LD50: 8580 mg/kg; Intravenous-mouse LD50: 4970 mg/kg

Flammability characteristics：

Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Packing level：

III

Hazard category：

Transport codes：

3077

RTECS Number：

XI0386500

Storage features：

The warehouse is low-temperature, ventilated and dry

Precautionary statement(s)：

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

Hazard Statements：

H317

GHS Classification：

|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

practically nontoxic

Toxicity Summary：

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.

Drug Information

Drug Indication：

For the treatment of serious infections caused by susceptible strains microorganisms.|FDA Label

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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

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.

Metabolism/Metabolites：

Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).

Biological Half-Life：

The half-life after an intravenous dose is 41 to 59 minutes.

Mechanism of Action：

The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.

MeSH Entry Terms：

Cefoxitin

Cefoxitin Use and Manufacturing

Uses

Antibacterial.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:427.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:8
Exact Mass:427.05079224
Monoisotopic Mass:427.05079224
Topological Polar Surface Area:202
Heavy Atom Count:28
Complexity:744
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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