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Cefacetrile

Cefacetrile structure

CAS No:
10206-21-0
Formula:
C13H13N3O6S
Chemical Name:
Cefacetrile
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-(2-cyanoacetamido)-3-(hydroxymethyl)-8-oxo-,acetate (ester);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[(cyanoacetyl)amino]-8-oxo-,(6R-trans)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-(2-cyanoacetamido)-3-(hydroxymethyl)-8-oxo-,acetate;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[(cyanoacetyl)amino]-8-oxo-,(6R,7R)-;(6R,7R)-3-[(Acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Cyanoacetamidocephalosporanic acid;Cefacetrile;Cephacetrile;Cephacetril;91768-90-0
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Pale Beige Solid

Solid

Cefacetrile is a cephalosporin.|A derivative of 7-aminocephalosporanic acid.|Cephacetrile is a broad-spectrum first-generation cephalosporin with antibacterial activity. Cephacetrile 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.

Cefacetrile Basic Attributes

Molecular Weight：

339.327

Exact Mass：

339.32

EC Number：

233-508-8

UNII：

FDM21QQ344

DSSTox ID：

DTXSID0022779

NCI Thesaurus Code：

C81037

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

162

XLogP3：

-0.45

Density：

1.59±0.1 g/cm3(Predicted)

Melting Point：

133-135°C

Boiling Point：

757.5±60.0 °C(Predicted)

Flash Point：

412ºC

Refractive Index：

1.639

Water Solubility：

2.43e+00 g/L

Storage Conditions：

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Vapor Pressure：

4.02E-25mmHg at 25°C

Safety Information

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

Toxicity

Protein Binding：

23 to 38%

Drug Information

Drug Indication：

Cefacetrile is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections.

Pharmacology：

Cefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.

MeSH：

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

Absorption：

Vd of 0.2 to 0.5L/.kg

Biological Half-Life：

1.2 hours

Mechanism of Action：

In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

MeSH Entry Terms：

C 36278 Ba

Cefacetrile Use and Manufacturing

A cephalosporin antibiotic.

Computed Properties

Molecular Weight:339.33
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:6
Exact Mass:339.05250632
Monoisotopic Mass:339.05250632
Topological Polar Surface Area:162
Heavy Atom Count:23
Complexity:664
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes