Cefmatilen

Chemical compound

none

Identifiers

IUPAC name

(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)- 2-(hydroxyimino)acetyl]amino}-8-oxo-3-{[(1H-1,2,3- triazol-4-ylsulfanyl)methyl]sulfanyl}-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS Number

140128-74-1^Y
154776-45-1 (HCl · H₂O)

PubChem CID

9690121

ChemSpider

4912110^Y

UNII

T750UM24H8

ChEMBL

ChEMBL2104438

CompTox Dashboard (EPA)

DTXSID50161236

Chemical and physical dataFormulaC₁₅H₁₄N₈O₅S₄Molar mass514.57 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=N\O)/C3=CSC(=N3)N)C(=O)O)SCSC4=NNN=C4

InChI

InChI=1S/C15H14N8O5S4/c16-15-18-5(2-30-15)8(21-28)11(24)19-9-12(25)23-10(14(26)27)6(3-29-13(9)23)31-4-32-7-1-17-22-20-7/h1-2,9,13,28H,3-4H2,(H2,16,18)(H,19,24)(H,26,27)(H,17,20,22)/b21-8-/t9-,13-/m1/s1^Y
Key:UEQVTKSAEXANEZ-YCRCPZNHSA-N^Y

(verify)

Cefmatilen (INN, codenamed S-1090) is an orally-active cephalosporin antibiotic. It was developed in Japan and first described in 1992.^[1]

In vitro, cefmatilen is highly active against a variety of Gram-positive and Gram-negative bacteria, including Streptococcus pyogenes and Neisseria gonorrhoeae.^[1]

References

^ ^a ^b Tsuji M, Ishii Y, Ohno A, Miyazaki S, Yamaguchi K (November 1995). "In vitro and in vivo antibacterial activities of S-1090, a new oral cephalosporin". Antimicrob Agents Chemother. 39 (11): 2544–51. doi:10.1128/aac.39.11.2544. PMC 162981. PMID 8585742.

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