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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15N5O7S2
Molecular Weight 453.4524
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFIXIME ANHYDROUS

SMILES

C=CC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N=C(/C(=N\OCC(=O)O)/c3csc(=N)[nH]3)O

InChI

InChIKey=OKBVVJOGVLARMR-QSWIMTSFSA-N
InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1

HIDE SMILES / InChI

Description

Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall. Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefixime interferes with an autolysin inhibitor. Cefixime is sold under the brand name Suprax, indicated for the treatment of: Uncomplicated Urinary Tract Infections Otitis Media Pharyngitis and Tonsillitis Acute Exacerbations of Chronic Bronchitis Uncomplicated Gonorrhea (cervical/urethral)

Originator

Approval Year

1986
41
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
3315
 9.91 pM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
4033
SUPRAX

Approved Use

To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator.

Launch Date

6.0972479E11
Curative
Approved
4033
SUPRAX

Approved Use

To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator.

Launch Date

6.0972479E11
Curative
Approved
4033
SUPRAX

Approved Use

To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator.

Launch Date

6.0972479E11
Curative
Approved
4033
SUPRAX

Approved Use

To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator.

Launch Date

6.0972479E11
Curative
Approved
4033
SUPRAX

Approved Use

To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator.

Launch Date

6.0972479E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.74 mg/L
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFIXIME ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
34.9 mg × h/L
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFIXIME ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFIXIME ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFIXIME ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2079371/
unhealthy, adult
n = 37
Health Status: unhealthy
Condition: ENT-infections
Age Group: adult
Sex: unknown
Population Size: 37
Sources:
https://pubmed.ncbi.nlm.nih.gov/2079371/
Other AEs: Perioral dermatitis...
Other AEs:
Perioral dermatitis (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2079371/
8 mg/kg 1 times / day multiple, oral
Recommended
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2188437/
unhealthy, children
n = 61
Health Status: unhealthy
Condition: urinary tract infections
Age Group: children
Sex: unknown
Population Size: 61
Sources:
https://pubmed.ncbi.nlm.nih.gov/2188437/
Sources:
https://pubmed.ncbi.nlm.nih.gov/2188437/
AEs

AEs

AESignificanceDosePopulation
Perioral dermatitis 1 patient
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2079371/
unhealthy, adult
n = 37
Health Status: unhealthy
Condition: ENT-infections
Age Group: adult
Sex: unknown
Population Size: 37
Sources:
https://pubmed.ncbi.nlm.nih.gov/2079371/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
753

activator
39
inhibitor
894

activator
7

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
38

CYP2B6
371

CYP2C8/9
23

CYP2C19
700

CYP2E1
424
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
63
 no
CYP1A
63
 no
CYP2B6
465
 no
CYP2B6
465
 no
CYP2C19
738
 no
CYP2C19
738
 no
CYP2C8/9
23
 no
CYP2C8/9
23
 no
CYP2D6
908
 no
CYP2D6
908
 no
CYP2E1
467
 no
CYP2E1
467
 no
CYP3A4
920
 no
CYP3A4
920
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
AK Scientific
K403
Alfa Chemistry
ACM97164562
BOC Sciences
97164-56-2
BioSynth
J-501698
Capot Chemical
13762
Hairui
HR131072
Hangzhou Yuhao Chemical Technology
RT14390
Hangzhou Yuhao Chemical Technology
RT14399
MolPort
MolPort-003-927-336
MolPort
MolPort-023-220-345
Molnova
M15976
TargetMol
T0932
Toronto Research Chemicals
C242800
Toronto Research Chemicals
C242820
Toronto Research Chemicals
Z438000
ZINC
ZINC000012503147
http://zinc15.docking.org/substances/ZINC000012503147
eMolecules
45919056
eMolecules
93409772
eNovation Chemicals
D767114
mcule
MCULE-2478205578
PubMed

PubMed

TitleDatePubMed
Double-blind comparison of cefixime and cefaclor in the treatment of acute otitis media in children.
1991
[Clinical evaluation of cefixime in pediatric respiratory tract infections].
1991 Jan
5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group.
1995
[Benign intracranial hypertension after treatment with pefloxacin].
1998 Aug
Nephrotic syndrome following cefixime therapy in a 10-month-old girl: spontaneous resolution without corticosteroid treatment.
1999 Oct
Investigation of the role of oligopeptide transporter PEPT1 and sodium/glucose cotransporter SGLT1 in intestinal absorption of their substrates using small GTP-binding protein Rab8-null mice.
2009 Mar
Diagnostic evaluation of hypersensitivity reactions to beta-lactam antibiotics in a large population of children.
2014 Feb
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

JP2000210076A
1
JP2001008679A
1
JP2001500477A
62
JP2002281959A
1
JP2002338470A
1
JP2002511777A
204
JP2002520419A
26
JP2003515526A
221
JP2004155793A
1
JP2004520358A
8
JP2009541210A
35
JP2011019462A
1
JP2011528275A
238
JP4739217B2
23
JP4792032B2
56
JP4849764B2
34
JPH01149728A
1
JPH02273624A
5
JPH07330607A
1
JPH10338694A
1
JPH11180985A
1

Sample Use Guides

In Vivo Use Guide
Adults: 400 mg daily Children: 8 mg/kg/day
Route of Administration: Oral
In Vitro Use Guide
A mosaic penicillin-binding protein 2 (PBP 2) was found in a single isolate that exhibited the highest cefixime MIC (0.5 mg/L).
Name Type Language
CEFIXIME ANHYDROUS
Common Name English
(6R,7R)-7-((2-(2-AMINO-1,3-THIAZOL-4-YL)-2-(CARBOXYMETHOXYIMINO)ACETYL)AMINO)-3-ETHENYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
CEFIXIME [MI]
Common Name English
CEFIXIME [WHO-DD]
Common Name English
CEFIXIME [INN]
Common Name English
ANHYDROUS CEFIXIME
Common Name English
Classification Tree Code System Code
WHO-ATC J01DD08
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
NDF-RT N0000175488
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
LIVERTOX 164
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
Code System Code Type Description
EVMPD
SUB07395MIG
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
EPA CompTox
79350-37-1
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
EVMPD
SUB70432
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
MERCK INDEX
M3195
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
DRUG BANK
DB00671
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
FDA UNII
XZ7BG04GJX
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
CAS
79350-37-1
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
PUBCHEM
5362065
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
RXCUI
1546021
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY RxNorm
INN
5678
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
NCI_THESAURUS
C170534
Created by admin on Sat Jun 26 06:38:03 UTC 2021 , Edited by admin on Sat Jun 26 06:38:03 UTC 2021
PRIMARY
SALT/SOLVATE (PARENT)
Structure of CEFIXIME
NIH
NCATS
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