Cefsulodin

Title: Cefsulodin
CAS Registry Number: 62587-73-9
CAS Name: 4-(Aminocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-phenylsulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium inner salt
Additional Names: 7-(a-sulphophenylacetamido)-3-(4¢-carbamoylpyridinium)methyl-3-cephem-4-carboxylic acid
Molecular Formula: C22H20N4O8S2
Molecular Weight: 532.55
Percent Composition: C 49.62%, H 3.79%, N 10.52%, O 24.03%, S 12.04%
Literature References: Third generation cephalosporin antibiotic. Prepn: S. Morimoto et al., DE 2234280; eidem, US 4065619 (1973, 1977 both to Takeda). Prepn and separation of isomers: H. Nomura et al., J. Med. Chem. 17, 1312 (1974). In vitro and in vivo antibacterial activity: K. Tsuchiya et al., Antimicrob. Agents Chemother. 13, 137 (1978). Absorption, distribution, excretion in mice, rats, dogs: eidem, J. Antibiot. 31, 593 (1978). Activity and susceptibility to b-lactamases: A. King et al., Antimicrob. Agents Chemother. 17, 165 (1980). In vitro comparison with other antibacterials: H. Grimm, Arzneim.-Forsch. 30, 1478 (1980). Clinical pharmacology: J. Fuellhaas et al., Curr. Chemother., Proc. 10th Int. Congr. Chemother. (Washington, D.C., 1978) 2, 848-851. Review of activity: H. C. Neu, B. E. Scully, Rev. Infect. Dis. 6, Suppl. 3, S667-S677 (1984). Review: A. Bryskier, Lyon Pharm. 34, 343-355 (1983); D. B. Wright, Drug Intell. Clin. Pharm. 20, 845-849 (1986).
Derivative Type: Sodium salt
CAS Registry Number: 52152-93-9
Additional Names: Sulcephalosporin
Manufacturers' Codes: Abbott 46811; CGP-7174/E; SCE-129
Trademarks: Cefomonil (TAP); Monaspor (Novartis); Pseudocef (Grenthal); Pyocefal (Cassenne-Takeda); Takesulin (Takeda); Tilmapor (Novartis); Ulfaret (Takeda)
Molecular Formula: C22H19N4NaO8S2
Molecular Weight: 554.53
Percent Composition: C 47.65%, H 3.45%, N 10.10%, Na 4.15%, O 23.08%, S 11.56%
Properties: Colorless needles from ethanol/water, mp 175° (dec). LD50 in mice (mg/kg): >4000 i.p.; >15000 orally (Bryskier).
Melting point: mp 175° (dec)
Toxicity data: LD50 in mice (mg/kg): >4000 i.p.; >15000 orally (Bryskier)
Derivative Type: d-Form sodium salt
Properties: [a]D23 +16.5° (c = 1.08 in water). uv max (water): 263 nm (e 14600).
Optical Rotation: [a]D23 +16.5° (c = 1.08 in water)
Absorption maximum: uv max (water): 263 nm (e 14600)
Derivative Type: l-Form sodium salt
Properties: [a]D23 -16.8° (c = 1.01 in water).
Optical Rotation: [a]D23 -16.8° (c = 1.01 in water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefteram Ceftezole Ceftibuten Ceftizoxime Ceftobiprole Medocaril

Cefsulodin
Cefsulodin.png
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 52152-93-9 YesY
ATC code J01DD03
PubChem CID 5284530
ChemSpider 4447588 YesY
UNII OV42LHE42B YesY
KEGG D02005 YesY
ChEMBL CHEMBL1617285 N
Chemical data
Formula C22H21N4O8S2+
Mol. mass 533.556 g/mol
 N (what is this?)  (verify)

Cefsulodin is a third generation cephalosporin antibiotic that has very specific activity against Pseudomonas aeruginosa. It has no significant activity against other Gram-negative bacteria and very limited activity against Gram-positive bacteria and anaerobic bacteria. Cefsulodin was first synthesized and patented by the Takeda Pharmaceutical Company in 1977. In 2002, Takeda stopped production of Cefsulodin. Many years of low-stability cefsulodin production has led to a widespread reduction of laboratory and research usages. Current attempts (i.e. IDEXX Laboratories) of increasing purity and stability of cefsulodin center around recrystallization. Typically the process entails the following: Cefsulodin is dissolved in an organic solvent, sodium, water or any mixture thereof, then subsequently recrystallized through separation of the unwanted fraction. Recently, TOKU-E has found that the main cause of cefsulodin instability stems from one key impurity in 7-ACA (7-aminocephalosporanic acid- a raw material used in the synthesis of cefsulodin). In order to produce high-purity, high-stability cefsulodin, TOKU-E uses industrial HPLC to remove significant quantities of this impurity in 7-ACA and thus produces ultra-pure, ultra-stable, and ultra potent cefsulodin.[1]