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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
MOL RATIO 3 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency
9.91 pM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SUPRAX
Curative
SUPRAX
Curative
SUPRAX
Curative
SUPRAX
Curative
SUPRAX

Cmax

ValueDoseCo-administeredAnalytePopulation
4.74 mg/L
400 mg 1 times / day steady-state, oral
CEFIXIME ANHYDROUS serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
34.9 mg × h/L
400 mg 1 times / day steady-state, oral
CEFIXIME ANHYDROUS serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
400 mg 1 times / day steady-state, oral
CEFIXIME ANHYDROUS serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
400 mg 1 times / day steady-state, oral
CEFIXIME ANHYDROUS serum
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Sourcing

PubMed

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).
Substance Class Chemical
Record UNII
97I1C92E55
Record Status Validated (UNII)
Record Version