| Identification | More | [Name]
Cefpirome sulfate | [CAS]
98753-19-6 | [Synonyms]
1-[[(6r,7r)-7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5h-cyclopenta[b]pyridinium sulfate
CEFPIROME SULFATE
(6r-rboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-
5h-1-pyrindinium,1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-ca
7-beta(z)))-(6-alphsulfate(1:1)
hr810sulfate
Cefquinome sulphate
CefpiromeSulfateC22H22N6O5S2H2So4
CefpiromeSulfate3%
1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-cyclopenta[b]pyrindinium Inner Salt
Broact
Cefrom
Keiti
Quinolinium, 1-(6R,7R)-7-(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetylamino-2-carboxy-8-oxo-5-thia-1-azabicyclo4.2.0oct-2-en-3-ylmethyl-5,6,7,8-tetrahydro-, inner salt
5H-Cyclopenta[b]pyridinium, 1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-, sulfate (1:1)
Keiten
1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridinium sulfate
cefpiromeSodium
Keitin)
Cefquinome base | [EINECS(EC#)]
685-392-7 | [Molecular Formula]
C22H24N6O9S3 | [MDL Number]
MFCD01688770 | [Molecular Weight]
612.66 | [MOL File]
98753-19-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Powder | [Melting point ]
198-2020C (dec) | [alpha ]
25D -4.7° (c = 5 in H2O) | [RTECS ]
UW8970000 | [storage temp. ]
Store at 0-5°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [color ]
White to Off-White | [Usage]
Fourth generation cephalosporin antibiotic | [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) |
| Hazard Information | Back Directory | [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]
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 |
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