Cefbuperazone
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| Category | Antibiotics |
| Catalog number | BBF-00715 |
| CAS | 76610-84-9 |
| Molecular Weight | 627.65 |
| Molecular Formula | C22H29N9O9S2 |
| Purity | 97% |
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Description
It is produced by the strain of Semisynthetic third generation cephalosporin for injection. It belongs to the cephalomycin-type compound.
Specification
| Related CAS | 76648-01-6 (sodium salt) |
| Synonyms | CEFBUPERAZONE; Cefbuperazona; Cefbuperazonum; Cerbuperazone; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-(((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)-3-hydroxy-1-oxobutyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6alpha,7alpha,7(2R*,3S*)))- |
| Storage | −20 °C under inert atmosphere |
| IUPAC Name | (6R,7S)-7-[[(2R,3S)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-3-hydroxybutanoyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CCN1CCN(C(=O)C1=O)C(=O)NC(C(C)O)C(=O)NC2(C3N(C2=O)C(=C(CS3)CSC4=NN=NN4C)C(=O)O)OC |
| InChI | InChI=1S/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1 |
| InChI Key | SMSRCGPDNDCXFR-CYWZMYCQSA-N |
Properties
| Appearance | Crystalline Powder |
| Melting Point | 118-120 °C (dec.) |
| Density | 1.77 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol, Water (Sonicated) |
Reference Reading
1. In vitro activity of cefbuperazone and other antimicrobial agents against isolates from the female genital tract
W K Hadley, R L Sweet, M J Ohm-Smith Antimicrob Agents Chemother . 1985 Jun;27(6):958-60. doi: 10.1128/AAC.27.6.958.
Cefbuperazone (BMY 25182), a new cephamycin, showed activity similar to those of moxalactam and other cephalosporin-cephamycins against aerobic and anaerobic bacteria from female genital tract infections. MICs of the antimicrobial agents were less than or equal to 16 micrograms/ml for greater than 97% of organisms tested. All of the anaerobic bacteria tested were susceptible to clindamycin, metronidazole, and chloramphenicol.
2. Experimental studies on the pharmacokinetics and therapeutic effect of cefbuperazone in biliary infection
J Kameyama, H Senda, T Asano, M Tsukamoto, N Murakami, K Amemiya, N Kaneda Curr Med Res Opin . 1989;11(9):577-84.
A study was carried out using an experimental biliary infection model to investigate the pharmacokinetic characteristics and therapeutic effect of cefbuperazone in the rabbit. Thirty rabbits were divided into three equal groups; a control group of normal animals, a group of infected animals receiving no cefbuperazone, and a group of infected animals receiving 50 mg cefbuperazone/kg intramuscularly. The experimental infection was made by direct inoculation of a suspension of E. coli into the common bile duct after ligation. The results showed that extremely high levels of cefbuperazone were achieved in bile and tissues of the biliary tract and were higher than those in the blood. Moreover, the levels were maintained at effective concentrations even after 6 hours. Viable bacterial cells from bile and the gall-bladder were barely detectable 24 and 48 hours after infection in the cefbuperazone-treated group, whilst counts remained high in the other infected group. White blood cell counts were increased at 24 hours after infection but were significantly lower in the cefbuperazone-treated group. Histological examination revealed marked inflammatory changes in the gall-bladder and bile duct of infected, untreated animals but few, mild changes only were seen in cefbuperazone-treated animals. Similarly, total bilirubin and liver enzymes were markedly increased in infected animals, but transaminases and alkaline phosphatase were significantly lower in the treated compared to the untreated group. The findings indicate, therefore, that cefbuperazone can be a useful antibiotic in biliary infection.
3. In vitro activity of Sch 34343 and cefbuperazone against anaerobic bacteria
J Wong, A W Chow, S D Shafran Antimicrob Agents Chemother . 1985 May;27(5):749-52. doi: 10.1128/AAC.27.5.749.
The in vitro activities of Sch 34343, a new penem antibiotic, and cefbuperazone, a new cephamycin antibiotic, were determined against 459 clinical anaerobic bacterial isolates and compared with the activities of imipenem and cefoxitin, respectively, by an agar dilution method. Both penems showed potent and similar activity against all anaerobic bacteria tested, particularly Peptococcus spp., Bacteroides fragilis, and Clostridium perfringens. All organisms except a single strain of Fusobacterium necrogenes were inhibited by an 8 micrograms/ml concentration of either Sch 34343 or imipenem. Overall, gram-positive bacilli, particularly Lactobacillus species, Clostridium difficile, and Bifidobacterium and Actinomyces species, were relatively more resistant to either penem than other genera of anaerobic bacteria tested. Cefbuperazone demonstrated only modest activity against a wide spectrum of anaerobic bacteria. It had excellent and selective activity against B. fragilis and Bacteroides vulgatus but was highly inactive against Bacteroides distasonis and Bacteroides thetaiotaomicron within the B. fragilis group. Both cephamycins showed virtually no activity against C. difficile and Lactobacillus spp. Although cefbuperazone was more active against Bifidobacterium spp., it had less activity against Fusobacterium spp., Eubacterium spp., and all Bacteroides spp. other than B. fragilis and B. vulgatus.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
