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Cefonicid

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Cefonicid
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
ATC code	J01DC06 (WHO)
Identifiers
IUPAC name (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetyl)amino]-8-oxo- 3-{[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl}- 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	61270-58-4
PubChemCID	43594
ChemSpider	39734^Y
UNII	6532B86WFG
KEGG	D07644^Y
ChEBI	CHEBI:3491^Y
ChEMBL	ChEMBL1601^Y
CompTox Dashboard(EPA)	DTXSID7022758
Chemical and physical data
Formula	C₁₈H₁₈N₆O₈S₃
Molar mass	542.56 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O
InChI InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1^Y Key:DYAIAHUQIPBDIP-AXAPSJFSSA-N^Y
(verify)

Cefonicide (orcefonicid) is acephalosporin antibiotic.^[1]

It has a density of 1.92g/cm³.

Synthesis

[edit]

Injectable semi-synthetic cephalosporin antibiotic related tocefamandole,q.v.

Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of1 with the appropriately substituted tetrazole thiole2. The mandelic acid amide C-7 side chain is reminiscent ofcefamandole.

References

[edit]

^Saltiel E, Brogden RN (September 1986). "Cefonicid. A review of its antibacterial activity, pharmacological properties and therapeutic use".Drugs.32 (3):222–59.doi:10.2165/00003495-198632030-00002.PMID 3530703.S2CID 243051006.
^DE 2611270, Berges, David Alan, "Cephalosporin-Derivate [Cephalosporin derivatives]", published 1976-09-30, assigned toSmithKline Corp.
^D. A. Berges,U.S. patent 4,048,311 (1977 toSmith Kline).
^U.S. patent 4,093,723,U.S. patent 4,159,373 (1978, 1979 both toSmith Kline).

Antibacterials active on thecell wall andenvelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ /Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems /Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization:Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking:Ramoplanin^§

Intracellular