cefepime Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, cefalosporanic acid derivatives	535	88040-23-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cefepime dihydrochloride hydrate cefepime cefepime hydrochloride cefimen tsefepim cefepime HCl	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. Molecular weight: 480.56 Formula: C19H24N6O5S2 CLOGP: -5.97 LIPINSKI: 1 HAC: 11 HDO: 2 TPSA: 150.04 ALOGS: -4.49 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cefepime dihydrochloride hydrate
cefepime
cefepime hydrochloride
cefimen
tsefepim
cefepime HCl

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.

Molecular weight: 480.56
Formula: C19H24N6O5S2
CLOGP: -5.97
LIPINSKI: 1
HAC: 11
HDO: 2
TPSA: 150.04
ALOGS: -4.49
ROTB: 7

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
4	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	85 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.28 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	2.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.78 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.90 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 18, 1996	FDA	HOSPIRA INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Acute kidney injury	348.39	66.71	102	708	28020	2329255
Status epilepticus	322.92	66.71	61	749	2417	2354858
Encephalopathy	303.04	66.71	64	746	4497	2352778
Myoclonus	206.10	66.71	42	768	2441	2354834
Neurotoxicity	158.86	66.71	33	777	2097	2355178
Sepsis	142.42	66.71	47	763	18441	2338834
Pyrexia	137.52	66.71	61	749	53647	2303628
Drug reaction with eosinophilia and systemic symptoms	132.50	66.71	34	776	5484	2351791
Mental status changes	132.11	66.71	34	776	5548	2351727
Tubulointerstitial nephritis	131.89	66.71	29	781	2409	2354866
Klebsiella infection	124.28	66.71	23	787	794	2356481
Thrombocytopenia	113.37	66.71	40	770	19091	2338184
Rash	112.91	66.71	55	755	59503	2297772
Confusional state	111.21	66.71	42	768	24302	2332973
Febrile neutropenia	105.43	66.71	33	777	10849	2346426
Drug hypersensitivity	100.18	66.71	47	763	46596	2310679
Clostridium difficile infection	90.19	66.71	22	788	2868	2354407
Drug resistance	87.12	66.71	21	789	2603	2354672
Blood creatinine increased	81.70	66.71	27	783	10506	2346769
Renal failure	72.08	66.71	28	782	17321	2339954
Pancytopenia	67.84	66.71	24	786	11428	2345847

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Acute kidney injury	339.02	52.68	122	783	34822	1711054
Encephalopathy	249.74	52.68	61	844	4391	1741485
Myoclonus	189.00	52.68	43	862	2252	1743624
Tubulointerstitial nephritis	137.68	52.68	35	870	2923	1742953
Neurotoxicity	129.83	52.68	31	874	1993	1743883
Rash	126.59	52.68	63	842	38630	1707246
Drug ineffective	125.50	52.68	74	831	63727	1682149
Acute generalised exanthematous pustulosis	125.16	52.68	27	878	1095	1744781
Confusional state	121.05	52.68	51	854	21227	1724649
Status epilepticus	119.18	52.68	29	876	2017	1743859
Septic shock	110.75	52.68	37	868	8072	1737804
Pyrexia	110.19	52.68	61	844	46339	1699537
Thrombocytopenia	76.21	52.68	37	868	21212	1724664
Multiple organ dysfunction syndrome	76.06	52.68	29	876	9213	1736663
Clostridium difficile colitis	74.59	52.68	19	886	1585	1744291
Febrile neutropenia	74.36	52.68	30	875	11070	1734806
Drug reaction with eosinophilia and systemic symptoms	72.53	52.68	24	881	5046	1740830
Renal tubular necrosis	64.72	52.68	18	887	2101	1743775
Mental status changes	64.47	52.68	23	882	6052	1739824
Haemodialysis	60.97	52.68	18	887	2598	1743278
Neutropenia	60.03	52.68	30	875	18230	1727646
Enterococcal infection	58.70	52.68	14	891	887	1744989
Clostridium difficile infection	58.40	52.68	16	889	1765	1744111
Toxic epidermal necrolysis	58.27	52.68	17	888	2354	1743522
Botulism	55.95	52.68	8	897	23	1745853
Meningitis candida	54.10	52.68	7	898	6	1745870
Pancytopenia	53.71	52.68	24	881	11333	1734543
Drug resistance	53.09	52.68	17	888	3213	1742663
Drug hypersensitivity	53.07	52.68	26	879	15109	1730767

Pharmacologic Action:

Source	Code	Description
ATC	J01DE01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Fourth-generation cephalosporins
ATC	J01RA06	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
CHEBI has role	CHEBI:36047	antibacterial drug
FDA EPC	N0000175488	Cephalosporin Antibacterial
FDA CS	M0003827	Cephalosporins

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Infection due to Pseudomonas aeruginosa	indication	11218009
Pneumonia due to Streptococcus	indication	34020007
Pneumonia due to Pseudomonas	indication	41381004
Bacterial pneumonia	indication	53084003	DOID:874
Klebsiella cystitis	indication	60867007
Infectious disease of abdomen	indication	128070006
Bacterial infection due to Klebsiella pneumoniae	indication	186435004
Bacterial peritonitis	indication	197171003
Pneumococcal pneumonia	indication	233607000
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Streptococcus pyogenes infection	indication	302809008
Bacterial urinary infection	indication	312124009
Infection due to Staphylococcus aureus	indication	406602003
Urinary tract infection caused by Klebsiella	indication	369001000119100
Complicated Proteus UTI	indication
E. Coli Pyelonephritis	indication
Complicated Urinary Tract Infections	indication
Complicated Bacteroides Peritonitis	indication
Complicated Streptococcus Peritonitis	indication
Klebsiella Pyelonephritis	indication
Complicated E. Coli Peritonitis	indication
Enterobacter Pneumonia	indication
Complicated Klebsiella Peritonitis	indication
Proteus Pyelonephritis	indication
Myoclonus	contraindication	17450006
Colitis	contraindication	64226004	DOID:0060180
Blood coagulation disorder	contraindication	64779008	DOID:1247
Factor II deficiency	contraindication	73975000
Disorder of brain	contraindication	81308009	DOID:936
Seizure disorder	contraindication	128613002
Impaired renal function disorder	contraindication	197663003
Pseudomembranous enterocolitis	contraindication	397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.32	acidic
pKa2	13.31	acidic
pKa3	3.1	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Bacterial penicillin-binding protein	Enzyme		DACA_ECOLI DACB_ECOLI DACC_ECOLI FTSI_ECOLI PBP2_ECOLI PBPA_ECOLI PBPB_ECOLI	INHIBITOR				CHEMBL	CHEMBL

External reference:

ID	Source
D000077723	MESH_DESCRIPTOR_UI
4024049	VUID
N0000022054	NUI
C0055003	UMLSCUI
D01157	KEGG_DRUG
370371004	SNOMEDCT_US
d03882	MMSL
20481	RXNORM
96048006	SNOMEDCT_US
4024049	VANDF
004974	NDDF
807PW4VQE3	UNII
6092	INN_ID
CHEMBL186	ChEMBL_ID
123171-59-5	SECONDARY_CAS_RN
9WT	PDB_CHEM_ID
DB01413	DRUGBANK_ID
CHEBI:478164	CHEBI
CHEMBL1200962	ChEMBL_ID
5479537	PUBCHEM_CID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
CEFEPIME HYDROCHLORIDE AND DEXTROSE	HUMAN PRESCRIPTION DRUG LABEL	1	0264-3193	INJECTION, SOLUTION	1 g	INTRAVENOUS	NDA	19 sections
CEFEPIME HYDROCHLORIDE AND DEXTROSE	HUMAN PRESCRIPTION DRUG LABEL	1	0264-3195	INJECTION, SOLUTION	2 g	INTRAVENOUS	NDA	19 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	0338-1301	INJECTION, SOLUTION	1 g	INTRAVENOUS	NDA	18 sections
Cefepime Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3222	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	14 sections
Cefepime Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3223	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	14 sections
cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	25021-121	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	25021-122	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	44567-240	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	44567-241	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6144	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6145	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6146	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6147	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	63323-326	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	63323-340	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
CEFEPIME	HUMAN PRESCRIPTION DRUG LABEL	1	66288-8100	INJECTION, POWDER, FOR SOLUTION	100 g	INTRAVENOUS	ANDA	18 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	66794-209	INJECTION, POWDER, FOR SOLUTION	10 g	INTRAMUSCULAR	ANDA	15 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	66794-210	INJECTION, POWDER, FOR SOLUTION	20 g	INTRAVENOUS	ANDA	15 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	67184-1002	INJECTION, POWDER, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	67184-1003	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	67184-1004	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	71288-008	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	17 sections
Cefepime	HUMAN PRESCRIPTION DRUG LABEL	1	71288-009	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	17 sections