Details of the Drug

General Information of Drug (ID: DMHVWIK)

Drug Name
Cefepime
Synonyms
Axepim; CFPM; Cefepima; Cefepimum; Cepimax; Cepimex; Maxcef; Maxipime; Cefepima [Spanish]; Cefepimum [Latin]; BMY 28142; Axepim (TN); BMY-28142; Cefepime [USAN:INN]; Cepimax (TN); Cepimex (TN); Maxcef (TN); Maxipime (TN); Cefepime (USAN/INN); (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; (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; 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); 7beta-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(1-methylpyrrolidinium-1-yl)methyl]-3,4-didehydrocepham-4-carboxylate
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 480.6
Topological Polar Surface Area (xlogp) -0.1
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Bioavailability
The bioavailability of drug is 82.3% [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 2.2 mL/min/kg [4]
Elimination
85% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.0 +/- 0.3 hours (in normal patients) [4]
Metabolism
The drug is metabolized via the hepatic [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.78% [4]
Vd
The volume of distribution (Vd) of drug is 18.0 +/- 2.0 L [5]
Chemical Identifiers
Formula
C19H24N6O5S2
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
Canonical 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
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
InChIKey
HVFLCNVBZFFHBT-ZKDACBOMSA-N
Cross-matching ID
PubChem CID
5479537
ChEBI ID
CHEBI:478164
CAS Number
88040-23-7
DrugBank ID
DB01413
TTD ID
D0A1CB
VARIDT ID
DR00585

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein 2 (Bact mrdA) TTHWB7G MRDA_ECOLI Modulator [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cefepime (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefepime and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [9]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefepime and Plazomicin. Urinary tract infection [GC08] [10]

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 BDDCS applied to over 900 drugs
3 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
6 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7 A comparative trial of imipenem versus ceftazidime in the release of endotoxin and cytokine generation in patients with gram-negative urosepsis. Urosepsis Study Group. J Endotoxin Res. 2000;6(1):25-31.
8 Growth of Escherichia coli: significance of peptidoglycan degradation during elongation and septation. J Bacteriol. 2008 Jun;190(11):3914-22.
9 Cerner Multum, Inc. "Australian Product Information.".
10 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".