Cefsulodin

Cefsulodin

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
Identifiers
CAS Number	52152-93-9
ATC code	J01DD03 (WHO)
PubChem	CID 5284530
ChemSpider	4447588
UNII	OV42LHE42B
KEGG	D02005
ChEMBL	CHEMBL1617285
Chemical data
Formula	C22H21N4O8S2^+
Molar mass	533.556 g/mol
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 Key:SYLKGLMBLAAGSC-IKZMBGHXSA-N
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Cefsulodin is a third-generation cephalosporin antibiotic with 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 uses. Current attempts (i.e. IDEXX Laboratories) of increasing purity and stability of cefsulodin center around recrystallization. Typically, the process entails: Cefsulodin is dissolved in an organic solvent, sodium ions, water, or any mixture thereof, then subsequently recrystallized through separation of the unwanted fraction. Recently, TOKU-E has found the main cause of cefsulodin instability stems from one key impurity in 7-aminocephalosporanic acid, a raw material used in the synthesis of cefsulodin. 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 ultrapure, ultrastable, and ultrapotent cefsulodin.^[1]

General use

Cefuslodin is most commonly used in cefsulodin-irgasan-novobiocin agar to select for Yersinia microorganisms.^[2] This agar is most often used in water and beverage testing.

Susceptibility data

The following represents MIC susceptibility data for various P. aeruginosa strains.

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

^[3]

References

1. , TOKU-E Technical Application Sheet.
2. "BAM Media M35: Cefsulodin-Irgasan Novobiocin Agar or Yersinia Selective Agar". Retrieved 2 September 2012.
3. http://antibiotics.toku-e.com/antimicrobial_474.html