U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15N5O7S2.3H2O
Molecular Weight 507.495
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFIXIME

SMILES

O.O.O.[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OCC(O)=O)\C3=CSC(N)=N3)C(O)=O

InChI

InChIKey=IPYWNMVPZOAFOQ-NABDTECSSA-N
InChI=1S/C16H15N5O7S2.3H2O/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);3*1H2/b20-9-;;;/t10-,14-;;;/m1.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H15N5O7S2
Molecular Weight 453.45
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
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
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
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
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
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
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%
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:
unhealthy, adult
n = 37
Health Status: unhealthy
Condition: ENT-infections
Age Group: adult
Sex: unknown
Population Size: 37
Sources:
Other AEs: Perioral dermatitis...
Other AEs:
Perioral dermatitis (1 patient)
Sources:
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:
unhealthy, children
n = 61
Health Status: unhealthy
Condition: urinary tract infections
Age Group: children
Sex: unknown
Population Size: 61
Sources:
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:
unhealthy, adult
n = 37
Health Status: unhealthy
Condition: ENT-infections
Age Group: adult
Sex: unknown
Population Size: 37
Sources:
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
[Benign intracranial hypertension after treatment with pefloxacin].
1998 Aug
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

Sample Use Guides

Adults: 400 mg daily Children: 8 mg/kg/day
Route of Administration: Oral
A mosaic penicillin-binding protein 2 (PBP 2) was found in a single isolate that exhibited the highest cefixime MIC (0.5 mg/L).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:25 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:25 UTC 2023
Record UNII
97I1C92E55
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFIXIME
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CEFIXIME [USP-RS]
Common Name English
FK 027
Code English
(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-8-OXO-3-VINYL-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7(SUP 2)-(Z)-(O-(CARBOXYMETHYL)OXIME)TRIHYDRATE
Common Name English
SUPRAX
Brand Name English
CEFIXIME [USAN]
Common Name English
CITROPEN
Brand Name English
FR-17027
Code English
CEFIXIME TRIHYDRATE [MI]
Common Name English
FK-027
Code English
CEFIXIME HYDRATE [JAN]
Common Name English
CEPHORAL
Brand Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)((CARBOXYMETHOXY)IMINO)ACETYL)AMINO)-3-ETHENYL-8-OXO-, TRIHYDRATE, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
CEFIXIME TRIHYDRATE
WHO-DD  
Common Name English
CEFIXIME [MART.]
Common Name English
CEFIXIME HYDRATE
Common Name English
CL-284635
Code English
CEFIXIME [USP MONOGRAPH]
Common Name English
FR 17027
Code English
CL 284,635
Code English
CEFIXIME [VANDF]
Common Name English
CEFIXIME [ORANGE BOOK]
Common Name English
CEFIXIME [EP MONOGRAPH]
Common Name English
Cefixime trihydrate [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548666
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
NDF-RT N0000175488
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
LIVERTOX NBK548358
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
NCI_THESAURUS C357
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
WHO-VATC QJ01DD08
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
WHO-ATC J01DD08
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
Code System Code Type Description
USAN
Y-43
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL1541
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
DRUG BANK
DB00671
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
LACTMED
Cefixime
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
MERCK INDEX
m3195
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY Merck Index
DAILYMED
97I1C92E55
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
RXCUI
25033
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY RxNorm
CAS
125110-14-7
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
RS_ITEM_NUM
1097658
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
WIKIPEDIA
CEFIXIME
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
SMS_ID
100000160229
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
EVMPD
SUB01116MIG
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
PUBCHEM
5491577
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
EVMPD
SUB171326
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
DRUG CENTRAL
537
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
CHEBI
472657
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
MESH
D020682
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
FDA UNII
97I1C92E55
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
NCI_THESAURUS
C1100
Created by admin on Fri Dec 15 15:24:25 UTC 2023 , Edited by admin on Fri Dec 15 15:24:25 UTC 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC