Compound ID | 79

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Cefepime + enmetazobactam (Exblifep)

Synonym(s): AAI101  |  OCID 5090

Class: Beta-lactam + beta-lactamase inhibitor

Agent Type: Semisynthetic; Small molecule; Direct acting; Indirect acting; Antibiotic adjuvant;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Enterobacteriaceae; indicated for urinary tract infection, hospital and ventilation acquired bacterial pneumoniae, and complicated intraabdominal infection
Combined with other compounds: Yes
Description: A fourth generation cephalosporin combined with penicillanic acid sulfone
Institute where first reported: Allecra Therapeutics; Orchid Pharma
Year first mentioned: 2015
Highest developmental phase: Approved by FDA in 2024
Development status: Approved
Chemical structure(s):
Cefepime
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Molecular weight:
Iso. 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-]
InChI Key: HVFLCNVBZFFHBT-ZKDACBOMSA-N
Can. SMILES: C[N+]1(CCCC1)CC2=C(C(=O)[O-])N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\OC)/C4=CSC(=N4)N
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
Enmetazobactam
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Molecular weight:
Iso. SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])CN3C=C[N+](=N3)C
InChI Key: HFZITXBUTWITPT-YWVKMMECSA-N
Can. SMILES: C[C@]1(CN2C=C[N+](=N2)C)[C@H](C(=O)[O-])N3C(=O)C[C@H]3S1(=O)=O
InChI: InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/23653540
Guide to Pharmacology: cefepime
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4584277/
  • http://www.ncbi.nlm.nih.gov/pubmed/25712356
  • http://allecra.com/pipeline-2/

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