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Cefotetan

Cefotetan structure

CAS No:
69712-56-7
Formula:
C17H17N7O8S4
Chemical Name:
Cefotetan
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7S)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,[6R-(6α,7α)]-;1,3-Dithietane,5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid deriv.;(6R,7S)-7-[[[4-(2-Amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefotetan;Apacef
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefotetan is a semisynthetic cephamycin antibiotic that exerts its bactericidal effects by inhibition of cell-wall synthesis[1].

Cefotetan is a semi-synthetic second-generation cephamycin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl, methoxy and {[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino groups at the 3, 7alpha, and 7beta positions, respectively, of the cephem skeleton. It is resistant to a wide range of beta-lactamases and is active against a broad spectrum of aerobic and anaerobic Gram-positive and Gram-negative microorganisms. It has a role as an antibacterial drug. It is a conjugate acid of a cefotetan(2-).|A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.|Cefotetan is a semi-synthetic, broad-spectrum, beta-lactamase-resistant, second-generation cephalosporin antibiotic derived from cephalosporium. The bactericidal activity of cefotetan disodium is caused by an inhibition of bacterial cell wall synthesis via inhibition of cross-linking of peptidoglycans. This results in a reduction of cell wall stability and causes cell lysis. Cefotetan disodium is more active against gram-negative organisms and less active against gram-positive organisms compared to first-generation cephalosporins.

Cefotetan Basic Attributes

Molecular Weight：

575.62

Exact Mass：

575.62

EC Number：

277-834-9

DSSTox ID：

DTXSID1022762

NCI Thesaurus Code：

C61664

ATC Code：

J - Antiinfectives for systemic use

HScode：

2941906000

Characteristics

PSA：

321

XLogP3：

0.1

Density：

2.1±0.1 g/cm3

Melting Point：

173-178°C (dec.)

Refractive Index：

1.921

Storage Conditions：

Store at 0-5°C

Toxicity：

Peritoneal-rat LD50: 8250 mg/kg; peritoneal-mouse LD50: 8120 mg/kg

Flammability characteristics：

Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Transport codes：

NONH for all modes of transport

RTECS Number：

XI0330800

Storage features：

The warehouse is low-temperature, ventilated and dry

Precautionary statement(s)：

P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501

Hazard Statements：

H315

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 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

practically nontoxic

Protein Binding：

Cefotetan is 88% plasma protein bound.

Drug Information

Drug Indication：

For prophylaxis and treatment of bacterial infections.|FDA Label

Pharmacology：

Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

MeSH：

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

Absorption：

No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.|10.4 L [elderly patients (greater than 65 years) with normal renal function]|1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]

Metabolism/Metabolites：

Biological Half-Life：

In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged

Mechanism of Action：

The bactericidal action of cefotetan results from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis.

MeSH Entry Terms：

Apacef

Cefotetan Use and Manufacturing

Uses

An antibiotic related to Cephalosporin, used in the treatment of bacterial infections.

Use Classification：

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

Computed Properties

Molecular Weight:575.6
XLogP3:0.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:9
Exact Mass:575.00214522
Monoisotopic Mass:575.00214522
Topological Polar Surface Area:321
Heavy Atom Count:36
Complexity:1090
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Cefotetan

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Cefotetan

CAS No.: 69712-56-7

Content: 99.00%

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