Cefepime

Cefepime

Systematic (IUPAC) name
(6R,7R,Z)- 7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)- 3-((1-methylpyrrolidinium-1-yl)methyl)-8-oxo-5-thia- 1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate
Clinical data
Trade names	Maxipime
AHFS/Drugs.com	monograph
MedlinePlus	a698021
Pregnancy cat.	B1 (Au)
Legal status	S4 (Au)
Routes	Intravenous, intramuscular
Pharmacokinetic data
Bioavailability	100% (IM)
Metabolism	Hepatic 15%
Half-life	2 hours
Excretion	Renal 70–99%
Identifiers
CAS number	88040-23-7 Y
ATC code	J01DE01
PubChem	CID 5479537
DrugBank	DB01413
ChemSpider	4586395 Y
UNII	807PW4VQE3 Y
KEGG	D02376 Y
ChEBI	CHEBI:478164 Y
ChEMBL	CHEMBL186 Y
Chemical data
Formula	C19H24N6O5S2
Mol. mass	480.56 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1 Y Key:HVFLCNVBZFFHBT-ZKDACBOMSA-N Y
Y(what is this?)  (verify)

Cefepime (INN) (pronounced /ˈsɛfɨpiːm/, /ˈkɛfɨpiːm/) is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both Gram-negative and Gram-positive organisms than third-generation agents. Cefepime hydrochloride was first marketed in 1994 and is currently marketed under various trade names including Neopime(Neomed)Maxipime, Maxcef, Cepimax, Cepimex, and Axepim. A 2007 meta-analysis suggested that when data of trials were combined, mortality was increased in patients treated with cefepime compared with other β-lactam antibiotics.^[1] In response, the U.S. Food and Drug Administration performed their own meta-analysis which found that there was no mortality difference.^[2]

Clinical use

Main article: Cephalosporin

Cefepime is usually reserved to treat moderate-severe nosocomial pneumonia, infections caused by multi-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.^[3] The use of cefepime might become less common, since it has been associated to an increase mortality when used for different types of infections. <-- not true since 2009 - http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/DrugSafetyInformationforHeathcareProfessionals/ucm167254.htm fix pls

Cefepime has good activity against important pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, and multiple drug resistant Streptococcus pneumoniae. A particular strength is its activity against Enterobacteriaceae. Whereas other cephalosporins are degraded by many plasmid- and chromosome-mediated beta-lactamases, cefepime is stable and is a front line agent when infection with Enterobacteriaceae is known or suspected.

Chemistry

The combination of the syn-configuration of the methoxyimino moiety and the aminothiazolyl moiety confers extra stability to β-lactamase enzymes produced by many bacteria. The N-methylpyrrolidine moiety increases penetration into Gram-negative bacteria. These factors increases the activity of cefepime against otherwise resistant organisms including Pseudomonas aeruginosa and Staphylococcus aureus.

References

1. ^ Yahav D, Paul M, Fraser A, Sarid N, Leibovici L (2007). "Efficacy and safety of cefepime: a systematic review and meta-analysis". Lancet Infect Dis 7 (5): 338–48. doi:10.1016/S1473-3099(07)70109-3. PMID 17448937. 
2. ^ "Information for Healthcare Professionals: Cefepime (marketed as Maxipime)". http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/DrugSafetyInformationforHeathcareProfessionals/ucm167254.htm. Retrieved 2009-08-02. 
3. ^ Chapman TM, Perry CM (2003). "Cefepime: a review of its use in the management of hospitalized patients with pneumonia". Am J Respir Med 2 (1): 75–107. PMID 14720024. 

External links

• Maxipime fact sheet – Elan Pharmaceuticals
• [1]- "POTENTOX" A unique combination of CEFEPIME AND AMIKACIN for resistant pathogen - Venus Remedies Limited,#51/52,Industrial Area,Phase -1,Panchkula,Haryana - INDIA [2]