Ceforanide

Chemical compound

J01DC11 (WHO)

Pharmacokinetic dataProtein binding80.6%MetabolismNilElimination half-life2.6 to 2.98 hoursExcretionRenalIdentifiers

IUPAC name

(6R,7R)-7-{[2-[2-(aminomethyl)phenyl]acetyl]amino}-3-
{[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl}-8-oxo-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS Number

60925-61-3^Y

PubChem CID

43507

DrugBank

DB00923^Y

ChemSpider

39656^Y

UNII

8M1YF8951V

KEGG

D00259^Y

ChEBI

CHEBI:3495^Y

ChEMBL

ChEMBL1201046^N

NIAID ChemDB

007642

CompTox Dashboard (EPA)

DTXSID1022760

Chemical and physical dataFormulaC₂₀H₂₁N₇O₆S₂Molar mass519.55 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3ccccc3CN)CSc4nnnn4CC(=O)O)C(=O)O

InChI

InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1^Y
Key:SLAYUXIURFNXPG-CRAIPNDOSA-N^Y

^NY (what is this?) (verify)

Ceforanide is a second-generation cephalosporin antibiotic.^{[citation needed]}

References

External links

Crowle A, Sbarbaro J, May M (1988). "Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages". Tubercle. 69 (1): 15–25. doi:10.1016/0041-3879(88)90036-0. PMID 3140456.
Campoli-Richards D, Lackner T, Monk J (1987). "Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy". Drugs. 34 (4): 411–37. doi:10.2165/00003495-198734040-00001. PMID 3315624. S2CID 242440792.
Cone L, Barton S, Woodard D (1987). "Treatment of scleroma with ceforanide". Arch Otolaryngol Head Neck Surg. 113 (4): 374–6. doi:10.1001/archotol.1987.01860040036012. PMID 3814386.

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^§