Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H22N6O5S2.H2O4S |
Molecular Weight | 612.656 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.[H][C@]12SCC(C[N+]3=C4CCCC4=CC=C3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C5=CSC(N)=N5)C([O-])=O
InChI
InChIKey=RKTNPKZEPLCLSF-QHBKFCFHSA-N
InChI=1S/C22H22N6O5S2.H2O4S/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27;1-5(2,3)4/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32);(H2,1,2,3,4)/b26-15-;/t16-,20-;/m1./s1
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/9211085Curator's Comment: description was created based on several sources, including
http://www.drugsupdate.com/generic/view/769/Cefpirome
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9211085
Curator's Comment: description was created based on several sources, including
http://www.drugsupdate.com/generic/view/769/Cefpirome
Cefpirome is a semisynthetic, broad-spectrum, fourth-generation cephalosporin with antibacterial activity. Cefpirome binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis. Cefpirome is an injectable extended-spectrum or 'fourth generation' cephalosporin. Its antibacterial activity encompasses many of the pathogens involved in hospital-acquired infections such as Enterobacteriaceae, methicillin-susceptible Staphylococcus aureus, coagulase-negative staphylococci and viridans group streptococci. Cefpirome also has in vitro activity against Streptococcus pneumoniae regardless of penicillin susceptibility. It is stable against most plasmid- and chromosome-mediated beta-lactamases, with the exception of the extended-spectrum plasmid-mediated SHV enzymes. Intravenous cefpirome 2g twice daily has shown clinical efficacy comparable to that of ceftazidime 2g 3 times daily in the treatment of hospitalised patients with moderate to severe infections. Clinical response and bacteriological eradication rates were similar in patients with severe pneumonia or septicaemia treated with either cefpirome or ceftazidime. Cefpirome appeared more effective than ceftazidime in the eradication of bacteria in patients with febrile neutropenia in 1 study; however, clinical response rates were similar in the 2 treatment groups. The tolerability of cefpirome appears similar to that of ceftazidime and other third generation cephalosporins, diarrhoea being the most frequently observed event. Thus, cefpirome is likely to be a valuable extended-spectrum agent for the treatment of severe infections. Cefpirome offers improved coverage against some Gram-positive pathogens and Enterobacteriaceae producing class I beta-lactamases compared with the third generation cephalosporins, although this has yet to be demonstrated in clinical trials.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1601757
Curator's Comment: Mean CSF concentrations were 0.50 +/- 0.11 mg/L at 1-2 h post dose (n = 4), 0.57 +/- 0.13 mg/L at 2-4 h post dose (n = 4), 0.76 +/- 0.34 mg/L at 4-6 h post dose (n = 7), and 0.83 +/- 0.29 mg/L at 6-8.3 h post dose (n = 5). Blood:brain barrier permeability to cefpirome may not be a limiting factor as CSF concentrations were rapidly attained.
Originator
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9124983
intravenously in a dose of 1 g twice a day for the treatment course of 5-7-10 days
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/17642976
Curator's Comment: n the gram positive group of organisms (Staphylococcus aureus and coagulase negative staphylococci); 96 strains out of 177 (54.2%) were resistant to cefpirome (Cpo). In the Enterobacteriaceae group, 66.0% of the isolates were resistant to Cpo; while for Pseudomonas and other non-fermentors, the corresponding figures were 70.7% for Cpo. The MIC for the strains resistant to Cpo were found to be > 16 mg/L to > 256 mg/L.
The MIC for the strains resistant to cefpirome were found to be > 16 mg/L to > 256 mg/L.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C357
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DBSALT002707
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
CHEMBL65794
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
236104
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | RxNorm | ||
|
BA5ALU2ZT9
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
9960551
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
m3211
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID8046909
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
SUB01131MIG
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
AA-102
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
3503
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
C87463
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
98753-19-6
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY | |||
|
100000090532
Created by
admin on Fri Dec 15 15:42:32 GMT 2023 , Edited by admin on Fri Dec 15 15:42:32 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD