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

Stem definition	Drug id	CAS RN
antibiotics, cefalosporanic acid derivatives	537	79350-37-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cefixime cefixim cefiximine cefixoral	A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases. Molecular weight: 453.44 Formula: C16H15N5O7S2 CLOGP: 0.25 LIPINSKI: 1 HAC: 12 HDO: 4 TPSA: 184.51 ALOGS: -3.64 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cefixime
cefixim
cefiximine
cefixoral

A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.

Molecular weight: 453.44
Formula: C16H15N5O7S2
CLOGP: 0.25
LIPINSKI: 1
HAC: 12
HDO: 4
TPSA: 184.51
ALOGS: -3.64
ROTB: 8

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.40	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.06 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	41 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	29.33 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	47 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.24 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.31 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	3.20 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
April 28, 1989	FDA

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
Drug hypersensitivity	66.05	21.03	79	3027	265163	53080797
Gastroenteritis staphylococcal	43.40	21.03	7	3099	83	53345877
Secretion discharge	33.64	21.03	15	3091	10491	53335469
Panic attack	31.35	21.03	18	3088	21400	53324560
Mucocutaneous candidiasis	30.61	21.03	4	3102	8	53345952
Dysbiosis	29.89	21.03	7	3099	615	53345345
Biopsy colon abnormal	27.44	21.03	5	3101	126	53345834
Movement disorder	25.48	21.03	15	3091	18666	53327294
Gastrointestinal mucosa hyperaemia	25.45	21.03	5	3101	190	53345770
Pulmonary congestion	24.77	21.03	14	3092	16142	53329818
Oligohydramnios	23.79	21.03	10	3096	6066	53339894
Vaginal infection	23.08	21.03	10	3096	6531	53339429
Foetal growth restriction	22.19	21.03	10	3096	7164	53338796
Premature baby	22.14	21.03	14	3092	19787	53326173
Pulmonary mass	22.00	21.03	14	3092	19990	53325970
Candida test positive	21.85	21.03	6	3100	998	53344962
Disorientation	21.43	21.03	18	3088	39341	53306619

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
Oral pustule	44.37	25.15	8	1423	254	32511841
Psoriatic arthropathy	36.14	25.15	17	1414	17843	32494252

Pharmacologic Action:

Source	Code	Description
ATC	J01DD08	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Third-generation cephalosporins
ATC	J01RA15	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
CHEBI has role	CHEBI:36047	antibacterial drugs
CHEBI has role	CHEBI:88188	allergenic drug
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Acute otitis media	indication	3110003
Gonorrhea	indication	15628003	DOID:7551
Acute gonococcal cervicitis	indication	20943002	DOID:10615
Acute gonococcal urethritis	indication	29864006
Bronchitis	indication	32398004	DOID:6132
Streptococcal tonsillitis	indication	41582007
Upper respiratory infection	indication	54150009
Urinary tract infectious disease	indication	68566005
Tonsillitis	indication	90176007	DOID:10456
Acute bacterial bronchitis	indication	233598009
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Streptococcus pyogenes infection	indication	302809008
Infective otitis media	indication	312218008
Pharyngitis	indication	405737000	DOID:2275
Acute exacerbation of chronic bronchitis	indication	425748003
Haemophilus Influenzae Acute Otitis Media	indication
Haemophilus Influenzae Chronic Bronchitis	indication
Streptococcus Pneumoniae Chronic Bronchitis	indication
Haemophilus Influenzae Bronchitis	indication
Moraxella Catarrhalis Acute Otitis Media	indication
Streptococcus Pneumoniae Bronchitis	indication
Pneumonia due to Escherichia coli	off-label use	51530003
Acute bacterial sinusitis	off-label use	75498004
Haemophilus Parahaemolyticus Pneumonia	off-label use
Haemophilus Parainfluenzae Pneumonia	off-label use
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	2.45	acidic
pKa2	2.54	acidic
pKa3	3.24	Basic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
500MG/5ML	SUPRAX	LUPIN LTD	N202091	Feb. 20, 2013	RX	FOR SUSPENSION	ORAL	9233112	Dec. 14, 2028	METHODS FOR TREATING BACTERIAL INFECTIONS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		IC50	4.24	WOMBAT-PK
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1	Enzyme	P19174	PLCG1_HUMAN		IC50	5.92	CHEMBL
Bacterial penicillin-binding protein	Enzyme		PBPA_ECOLI PBPB_ECOLI DACC_ECOLI PBP2_ECOLI FTSI_ECOLI DACA_ECOLI DACB_ECOLI	INHIBITOR			CHEMBL	CHEMBL
Streptokinase A	Enzyme		STRP_STRP1		EC50	7.22	WOMBAT-PK

External reference:

ID	Source
4019391	VUID
N0000147544	NUI
D00258	KEGG_DRUG
C0060400	UMLSCUI
CHEBI:472657	CHEBI
C04	PDB_CHEM_ID
CHEMBL1541	ChEMBL_ID
D020682	MESH_DESCRIPTOR_UI
DB00671	DRUGBANK_ID
10898	IUPHAR_LIGAND_ID
125110-14-7	SECONDARY_CAS_RN
97I1C92E55	UNII
5362065	PUBCHEM_CID
25033	RXNORM
233747	MMSL
4374	MMSL
d00072	MMSL
002737	NDDF
387536009	SNOMEDCT_US
96052006	SNOMEDCT_US
4019391	VANDF

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	16714-766	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	27 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	16714-767	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	27 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-201	TABLET	400 mg	ORAL	ANDA	27 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-203	TABLET, CHEWABLE	100 mg	ORAL	ANDA	19 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-203	TABLET, CHEWABLE	100 mg	ORAL	ANDA	19 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-205	TABLET, CHEWABLE	200 mg	ORAL	ANDA	19 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-205	TABLET, CHEWABLE	200 mg	ORAL	ANDA	19 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-206	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	27 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-207	POWDER, FOR SUSPENSION	500 mg	ORAL	NDA	27 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	27437-208	CAPSULE	400 mg	ORAL	NDA	27 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	43598-673	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	22 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	43598-674	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	22 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	54348-797	CAPSULE	400 mg	ORAL	ANDA	27 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	62250-663	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	27 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	62250-664	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	27 sections
Cefixime	HUMAN PRESCRIPTION DRUG LABEL	1	62250-668	POWDER, FOR SUSPENSION	500 mg	ORAL	ANDA	27 sections
Cefixime	Human Prescription Drug Label	1	65862-751	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	25 sections
Cefixime	Human Prescription Drug Label	1	65862-752	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	25 sections
CEFIXIME	Human Prescription Drug Label	1	67877-584	CAPSULE	400 mg	ORAL	ANDA	24 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	68180-202	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	27 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	68180-405	POWDER, FOR SUSPENSION	100 mg	ORAL	ANDA	25 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	68180-407	POWDER, FOR SUSPENSION	200 mg	ORAL	ANDA	25 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	68180-416	CAPSULE	400 mg	ORAL	ANDA	25 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	68180-423	CAPSULE	400 mg	ORAL	NDA authorized generic	25 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	70518-2749	CAPSULE	400 mg	ORAL	ANDA	24 sections
CEFIXIME	HUMAN PRESCRIPTION DRUG LABEL	1	70518-3221	CAPSULE	400 mg	ORAL	NDA authorized generic	25 sections
SUPRAX	HUMAN PRESCRIPTION DRUG LABEL	1	70934-079	CAPSULE	400 mg	ORAL	NDA	28 sections