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Cefonicid

Cefonicid structure

CAS No:
61270-58-4
Formula:
C18H18N6O8S3
Chemical Name:
Cefonicid
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[(hydroxyphenylacetyl)amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-hydroxyphenylacetyl]amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-,(6R,7R)-;(6R,7R)-7-[[(2R)-2-Hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefonicid;Monicid;162143-29-5
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: A cephalosporin bearing {[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl and (R)-2-hydroxy-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.

Solid

Cefonicid is a cephalosporin bearing {[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl and (R)-2-hydroxy-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug. It is a conjugate acid of a cefonicid(2-).|A second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.|Cefonicid is a second-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. Cefonicid binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted.

Cefonicid Basic Attributes

Molecular Weight：

542.57

Exact Mass：

542.57

EC Number：

612-109-6

UNII：

6532B86WFG

DSSTox ID：

DTXSID7022758

NCI Thesaurus Code：

C65299

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

264

XLogP3：

-0.45

Density：

1.9±0.1 g/cm3

Refractive Index：

1.852

Water Solubility：

8.95e-01 g/L

Safety Information

Precautionary statement(s)：

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

Hazard Statements：

H317

Toxicity

Protein Binding：

98% bound to plasma proteins.

Drug Information

Drug Indication：

For the treatment of bacterial infections caused by susceptible microorganisms.

Pharmacology：

Cefonicid is a second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.

MeSH：

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

Metabolism/Metabolites：

Not metabolized.

Biological Half-Life：

4.5 hours

Mechanism of Action：

Cefonicid, like the penicillins, is a beta-lactam antibiotic. 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：

Cefonicid

Cefonicid Use and Manufacturing

A semi-synthetic cephalosporin antibiotic related to Cefamandole. Antibacterial

Computed Properties

Molecular Weight:542.6
XLogP3:-1.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:9
Exact Mass:542.03482507
Monoisotopic Mass:542.03482507
Topological Polar Surface Area:264
Heavy Atom Count:35
Complexity:999
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl acetate

Sodium bicarbonate

Isopropanol