Cefsulodin

Chemical compound

J01DD03 (WHO)

Identifiers

IUPAC name

4-(aminocarbonyl)-1-[((6R,7R)-2-carboxy-8-oxo-7-{[phenyl(sulfo)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]pyridinium

CAS Number

62587-73-9^Y
Sodium salt: 52152-93-9^Y

PubChem CID

5284530

ChemSpider

4447588^Y

UNII

OV42LHE42B
Sodium salt: 2D087186PY^Y

KEGG

D02005^Y

ChEMBL

ChEMBL1617285^N

CompTox Dashboard (EPA)

DTXSID6022769

Chemical and physical dataFormulaC₂₂H₂₁N₄O₈S₂⁺Molar mass533.55 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(c3ccccc3)S(=O)(=O)O)C[n+]4ccc(C(=O)N)cc4)C([O-])=O

InChI

InChI=1S/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17?,21-/m1/s1^Y
Key:SYLKGLMBLAAGSC-IKZMBGHXSA-N^Y

^NY (what is this?) (verify)

Cefsulodin is a third-generation cephalosporin antibiotic that is active against Pseudomonas aeruginosa and was discovered by Takeda Pharmaceutical Company in 1977.^[1]^[2]^[3]^[4]

TAP Pharmaceuticals had a new drug application on file with FDA for cefsulodin under the brand name Cefonomil as of 1985.^[5]

Cefsulodin is most commonly used in cefsulodin-irgasan-novobiocin agar to select for Yersinia microorganisms.^[6] This agar is most often used in water and beverage testing.^{[citation needed]}

Susceptibility data

The following represents MIC susceptibility data for various P. aeruginosa strains:^[7]

Pseudomonas aeruginosa PA13 (resistant strain): 32 μg/ml
Pseudomonas aeruginosa (wild-type, susceptible): 4 - 8 μg/ml

References

^ "TOKU-E Technical Application Sheet" (PDF). Archived from the original (PDF) on 27 September 2011.
^ Smith BR (1984). "Cefsulodin and ceftazidime, two antipseudomonal cephalosporins". Clinical Pharmacy. 3 (4): 373–85. PMID 6380902.
^ Neu HC, Scully BE (1984). "Activity of cefsulodin and other agents against Pseudomonas aeruginosa". Reviews of Infectious Diseases. 6 (Suppl 3): S667–77. doi:10.1093/clinids/6.supplement_3.s667. PMID 6443768.
^ Wright DB (November 1986). "Cefsulodin". Drug Intelligence & Clinical Pharmacy. 20 (11): 845–9. doi:10.1177/106002808602001104. PMID 3536385. S2CID 243377437.
^ "Lupron Is First Abbott-Takeda Product to Reach U.S. Market". Pink Sheet. 15 April 1985.
^ "BAM Media M35: Cefsulodin-Irgasan Novobiocin Agar or Yersinia Selective Agar". Food and Drug Administration. Retrieved 2 September 2012.
^ "Cefsulodin | the Antimicrobial Index Knowledgebase - TOKU-E".

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-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

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§