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]
Staphylococcus aureus infection	N.A.	Approved	[2]
Streptococcal pneumonia	N.A.	Approved	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

480.6

Logarithm of the Partition Coefficient (xlogp)

-0.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: The bioavailability of drug is 82.3% []
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 [3]
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 []
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 []

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

Repurposed Drugs (RPD)

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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	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Dihydrofolate reductase (DHFR)	OT3DVIGM	DYR_HUMAN	Gene/Protein Processing	[6]
HLA class II histocompatibility antigen, DRB1 beta chain (HLA-DRB1)	OTRGGIFP	DRB1_HUMAN	Gene/Protein Processing	[7]
Rho GTPase-activating protein 45 (ARHGAP45)	OTL86FEQ	HMHA1_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]	[8]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Cefepime and Plazomicin.	Urinary tract infection [GC08]	[9]
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References

1	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2	Cefepime FDA Label
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6	Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity. J Biochem Mol Toxicol. 2015 Mar;29(3):135-9.
7	Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
8	Cerner Multum, Inc. "Australian Product Information.".
9	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".