CEFPIROME

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H22N6O5S2
Molecular Weight	514.577
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[N+]3=C4CCCC4=CC=C3)=C(N2C1=O)C([O-])=O)C5=CSC(N)=N5

InChI

InChIKey=DKOQGJHPHLTOJR-WHRDSVKCSA-N

InChI=1S/C22H22N6O5S2/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/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1

HIDE SMILES / InChI

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 31 Target ID: CHEMBL2362972 Sources: http://www.drugsupdate.com/generic/view/769/Cefpirome	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://adisinsight.springer.com/drugs/800000486	Curative		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
57.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
86.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
36.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
59.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
119 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	2000 mg single, intravenous dose: 2000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
91 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day steady-state, intravenous dose: 1000 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
85.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
58.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
131 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
150 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
77.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
119 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
84 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
138 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
259 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	2000 mg single, intravenous dose: 2000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
124 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day steady-state, intravenous dose: 1000 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
117 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
128 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
127 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
242 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
306 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	2000 mg single, intravenous dose: 2000 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day steady-state, intravenous dose: 1000 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.76 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1564130/	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10401943/	2 g 2 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered: CIPROFLOXACIN	CIPROFLOXACIN	CEFPIROME plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9506005/			CEFPIROME plasma	Homo sapiens

Doses

Dose	Population	Adverse events
1 g 2 times / day multiple, intramuscular Highest studied dose Dose: 1 g, 2 times / day Route: intramuscular Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1601759/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1601759/	Other AEs: Headache... Other AEs: Headache (mild, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1601759/
2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	Disc. AE: Skin rash... Other AEs: Anemia, Diarrhea... AEs leading to discontinuation/dose reduction: Skin rash (1 pt) Other AEs: Anemia (2 patients) Diarrhea (1 pt) Nausea (1 pt) Headache (1 pt) Aspartate aminotransferase increase (3 patients) alanine aminotransferase (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
50 mg/kg 1 times / day single, intravenous Highest studied dose Dose: 50 mg/kg, 1 times / day Route: intravenous Route: single Dose: 50 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8619595/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8619595/	Sources: https://pubmed.ncbi.nlm.nih.gov/8619595/

AEs

AE	Significance	Dose	Population
Headache	mild, 2 patients	1 g 2 times / day multiple, intramuscular Highest studied dose Dose: 1 g, 2 times / day Route: intramuscular Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1601759/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1601759/
Diarrhea	1 pt	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
Headache	1 pt	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
Nausea	1 pt	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
Skin rash	1 pt Disc. AE	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
Anemia	2 patients	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
Aspartate aminotransferase increase	3 patients	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/
alanine aminotransferase	3 patients	2 g 2 times / day multiple, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10965103/

PubMed

Title	Date	PubMed
In vitro activity of cefpirome: a new fourth generation cephalosporin.	2007-07-24	17642976

Patents

Sample Use Guides

In Vivo Use Guide

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

The MIC for the strains resistant to cefpirome were found to be > 16 mg/L to > 256 mg/L.

Name

Type

Language

CEFIR

Preferred Name

English

CEFPIROME

Official Name

English

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-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-

Systematic Name

English

cefpirome [INN]

Common Name

English

Cefpirome [WHO-DD]

Common Name

English

1-(((6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-6,7-DIHYDRO-5H-1-PYRINDINIUM HYDROXIDE, INNER SALT, 72-(Z)-(O-METHYLOXIME)

Systematic Name

English

HR-810 FREE BASE

Code

English

CEFPIROME [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01DE02