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Cefpirome

Cefpirome structure

CAS No:
84957-29-9
Formula:
C22H22N6O5S2
Chemical Name:
Cefpirome
Synonyms:
5H-Cyclopenta[b]pyridinium,1-[[(6R,7R)-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-,inner salt;5H-1-Pyrindinium,1-[[7-[[(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-,inner salt,[6R-[6α,7β(Z)]]-;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-,inner salt;HR 810;Cefpirome;Antibiotic HR 810;5H-Cyclopenta[b]pyridinium,1-[[7-[[(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-,inner salt,[6R-[6α,7β(Z)]]-;Cefrom
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefpirome is a fourth-generation cephalosporin. Trade names include Cefrom, Keiten, Broact, and Cefir. Cefpirome is considered highly active against Gram-negative bacteria, including Pseudomonas aeruginosa, and Gram-positive bacteria.

Cefpirome Basic Attributes

Molecular Weight：

514.58

Exact Mass：

514.10900

EC Number：

1592732-453-0

HScode：

3003201900

Characteristics

PSA：

207.46000

XLogP3：

-0.1339

Appearance：

White or almost white crystalline powder

Toxicity：

LD50 in mice, rats (g/kg): 1.9-2.4, 1.9-2.15 i.v.; 3.8-4.2, 5.8-6.55 i.p. (Donaubauer, Mayer)

Safety Information

hazard class code：

36/37/38-42/43

safety instructions：

22-26-36/37/39

Marks：

Precautionary statement(s)：

S22-S26-S36/37/39

Cefpirome Use and Manufacturing

Methods of Manufacturing

Cefotaxime (I) and 2, 3-cyclopentapyridine are heated in water in the presence of potassium iodide to obtain cefpirome. Or after converting its side chain to iodide, and 2, 3-cyclopentenopyridine refluxed in dichloromethane to obtain cefpirome. Or directly acylate with the active compound (III) and compound (IV) to obtain cefpirome.

Uses

Cephalosporin antibiotic Claforan

Computed Properties

Molecular Weight:514.6
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:6
Exact Mass:514.10931017
Monoisotopic Mass:514.10931017
Topological Polar Surface Area:208
Heavy Atom Count:35
Complexity:955
Defined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

104498-86-4

Material

Potassium iodide