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Cefepime
Also known as: Maxipime, 88040-23-7, Cefepima, Cefepimum [latin], Cefepima [spanish], Cefepimum
Molecular Formula
C19H24N6O5S2
Molecular Weight
480.6  g/mol
InChI Key
HVFLCNVBZFFHBT-ZKDACBOMSA-N
FDA UNII
807PW4VQE3

A fourth-generation cephalosporin antibacterial agent that is used in the treatment of infections, including those of the abdomen, urinary tract, respiratory tract, and skin. It is effective against PSEUDOMONAS AERUGINOSA and may also be used in the empiric treatment of FEBRILE NEUTROPENIA.
Cefepime is a Cephalosporin Antibacterial.
1 2D Structure

Cefepime

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 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
2.1.3 InChI Key
HVFLCNVBZFFHBT-ZKDACBOMSA-N
2.1.4 Canonical SMILES
C[N+]1(CCCC1)CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)[O-]
2.1.5 Isomeric SMILES
C[N+]1(CCCC1)CC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
807PW4VQE3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Axpim

2. Bmy 28142

3. Bmy-28142

4. Bmy28142

5. Cefepim

6. Cefepime Hydrochloride

7. Maxipime

8. Quadrocef

2.3.2 Depositor-Supplied Synonyms

1. Maxipime

2. 88040-23-7

3. Cefepima

4. Cefepimum [latin]

5. Cefepima [spanish]

6. Cefepimum

7. Bmy-28142

8. Cfpm

9. Axepim

10. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

11. 807pw4vqe3

12. 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)-1-methylpyrrolidinium Hydroxide, Inner Salt, 7(sup 2)-(z)-(o-methyloxime)

13. Vnrx-5022

14. Chebi:478164

15. J01de01

16. Bmy 28142

17. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

18. Cefepime (usan/inn)

19. Unii-807pw4vqe3

20. Cefepime [usan:inn:ban]

21. Cefepime, Antibiotic For Culture Media Use Only

22. Cefepime [usan]

23. Cefepime [inn]

24. Cefepime [mi]

25. Cefepime [vandf]

26. Cefepime [who-dd]

27. Chembl186

28. Schembl65720

29. Pyrrolidinium, 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)-1-methyl-, Hydroxide, Inner Salt, (6r-(6alpha,7beta(z)))-

30. Dtxsid70873208

31. Bcpp000292

32. Hms2089m18

33. Hy-b0692

34. Bdbm50350470

35. Akos015850865

36. Akos016014147

37. Bcp9000504

38. Db01413

39. 7beta-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(1-methylpyrrolidinium-1-yl)methyl]-3,4-didehydrocepham-4-carboxylate

40. As-76125

41. Cs-0009590

42. C-2468

43. C08111

44. D02376

45. Ab01275446-01

46. Q27294816

47. 1-{[(6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium

48. Pyrrolidinium, 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)-1-methyl-, Hydroxide, Inner Salt, (6r-(6.alpha.,7.beta.(z)))-

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 480.6 g/mol
Molecular Formula C19H24N6O5S2
XLogP3-0.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass480.12496023 g/mol
Monoisotopic Mass480.12496023 g/mol
Topological Polar Surface Area204 Ų
Heavy Atom Count32
Formal Charge0
Complexity869
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMaxipime
PubMed HealthCefepime (Injection)
Drug ClassesAntibiotic
Drug LabelMAXIPIME (cefepime hydrochloride, USP) is a semi-synthetic, broad spectrum, cephalosporin antibiotic for parenteral administration. The chemical name is 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)-glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0] o...
Active IngredientCefepime hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 500mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyHospira

2 of 2  
Drug NameMaxipime
PubMed HealthCefepime (Injection)
Drug ClassesAntibiotic
Drug LabelMAXIPIME (cefepime hydrochloride, USP) is a semi-synthetic, broad spectrum, cephalosporin antibiotic for parenteral administration. The chemical name is 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)-glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0] o...
Active IngredientCefepime hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 500mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyHospira

4.2 Drug Indication

For the treatment of pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae, or Enterobacter species. Also for empiric treatment of febrile neutropenic patients and uncomplicated and complicated urinary tract infections (including pyelonephritis) caused by Escherichia coli or Klebsiella pneumoniae, when the infection is severe, or caused by Escherichia coli, Klebsiella pneumoniae, or Proteus mirabilis, when the infection is mild to moderate, including cases associated with concurrent bacteremia with these microorganisms. Also for the treatment of uncomplicated skin and skin structure infections caused by Staphylococcus aureus (methicillin-susceptible strains only) or Streptococcus pyogenes and complicated intra-abdominal infections (used in combination with metronidazole) caused by Escherichia coli, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Enterobacter species, or Bacteroides fragilis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefepime is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime is active against Gram-positive and Gram-negative bacteria, with greater activity against both than third-generation antibiotics. Cefepime has good activity against important pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, Enterobacteriaceae, and multiple drug resistant Streptococcus pneumoniae. 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


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFEPIME
5.3.2 FDA UNII
807PW4VQE3
5.3.3 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DE - Fourth-generation cephalosporins

J01DE01 - Cefepime


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability of cefepime after an IM dose of 50 mg/kg was 82.3 (±15)% in eight patients.


Route of Elimination

Elimination of cefepime is principally via renal excretion with an average (SD) half-life of 2 (0.3) hours and total body clearance of 120 (8) mL/min in healthy volunteers. Cefepime is excreted in human milk.


Volume of Distribution

18.0 2.0 L

0.3 0.1 L/kg [Pediatric]


Clearance

120 mL/min [Healthy adult male receiving a single 30-minute IV infusions of cefepime]

3.3 +/-1.0 mL/min/kg [Petriatic patients (2 months 11 years of age) receiving a single IV dose]


5.6 Metabolism/Metabolites

Hepatic. Cefepime is metabolized to N-methylpyrrolidine (NMP) which is rapidly converted to the N-oxide (NMP-N-oxide).


5.7 Biological Half-Life

2.0 (± 0.3) hours in normal patients. The average half-life in patients requiring hemodialysis was 13.5 (± 2.7) hours and in patients requiring continuous peritoneal dialysis was 19.0 (± 2.0) hours.


5.8 Mechanism of Action

Cephalosporins are bactericidal and have the same mode of action as other beta-lactam antibiotics (such as penicillins). Cephalosporins disrupt the synthesis of the peptidoglycan layer of bacterial cell walls. The peptidoglycan layer is important for cell wall structural integrity, especially in Gram-positive organisms. The final transpeptidation step in the synthesis of the peptidoglycan is facilitated by transpeptidases known as penicillin binding proteins (PBPs).


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