Cefpirome sulfate Chemical Properties

Melting point:

198-2020C (dec)

alpha 

25D -4.7° (c = 5 in H2O)

RTECS 

UW8970000

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in DMSO

form 

Solid

color 

White to Off-White

λmax

265nm(Buffer)(lit.)

Merck 

14,1940

InChIKey

RKTNPKZEPLCLSF-YBZTWAOJNA-N

SMILES

S(=O)(O)(O)=O.C(C1CS[C@@H]2[C@H](NC(=O)/C(=N\OC)/C3N=C(N)SC=3)C(=O)N2C=1C(=O)[O-])[N+]1C2CCCC=2C=CC=1 |&1:9,10,r|

CAS DataBase Reference

98753-19-6(CAS DataBase Reference)

Safety Information

HS Code 

2941.90.3000

Cefpirome sulfate Usage And Synthesis

Description

Cefpirome sulfate is a new injectable cephalosporin indicated for the treatment of severe urinary and respiratory tract infections, including septicemia and nosocomial infections. Cefpirome sulfate is reported to be the first true fourth-generation cephalosporin due to its similar activities to third-generation antibiotics against Gram-positive bacteria and to first-generation antibiotics against Gram-negative bacteria. Its efficacy against P.aeruginosa is comparable to ceftazidime. The broad spectrum of activity includes Klebsiella, methicillin-sensitive staphylococci, penicillin-resistant pneumococci, E.coli which generates extended-spectrum beta-lactamases and multi-resistant organisms such as Citrobacter, Enterobacter and Serratia.

Chemical Properties

White Crystalline Powder

Originator

Hoechst AG (Germany)

Uses

A fourth generation cephalosporin antibiotic

Definition

ChEBI: Cefpirome sulfate is an azaheterocycle sulfate salt. It is functionally related to a cefpirome.

brand name

Cefrom (Hoechst-Roussel).

Synthesis

The present invention employs a microwave-assisted synthesis method to synthesize cefpirome hydrogensulfate in the following steps: (1) 7-aminocephalosporanic acid (2.72 g, 0.01 mol, Compound I) was mixed homogeneously with (Z)-S-2-benzothiazolyl-2-amino-alpha-(methoxyimino)-4-thiazole thioacetate (AEMA, 3.85 g, 0.011 mol, Compound VII) was homogeneously mixed and ground, followed by the addition of 2,3-cyclopentenopyridine (2.3 g, 0.011 mol, Compound IV) and concentrated sulfuric acid (10.88 g, 98 wt%). (2) The microwave reaction was carried out sequentially: 300 W for 1 min, 450 W for 1 min and 750 W for 2 min. (3) After completion of the reaction, deionized water (29.92 g) was added to the residue, mixed and filtered, the filtrate was collected and the solvent was removed to obtain a white solid. The resulting solid was dried under vacuum at 50 °C for 4 h. Cefpirome hydrogen sulfate (5.09 g, yield 99.0%, purity ≥99.9%) was finally obtained.

References

[1] Patent: CN105646542, 2016, A. Location in patent: Paragraph 0027; 0040; 0041; 0042; 0043; 0044; 0045

Cefpirome sulfate(98753-19-6)Related Product Information

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• calcium sulfate
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• Glycine
• Potassium sulfate
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• Colistin sulfate
• Cefpirome
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• Betaine
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• sulfate