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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15N5O7S2
Molecular Weight 453.45
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFIXIME ANHYDROUS

SMILES

NC1=NC(=CS1)C(=N\OCC(O)=O)\C(=O)N[C@H]2[C@H]3SCC(C=C)=C(N3C2=O)C(O)=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)

Approval Year

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 Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
LIVERTOX 164
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
Code System Code Type Description
EVMPD
SUB07395MIG
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
EPA CompTox
79350-37-1
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
LactMed
79350-37-1
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
EVMPD
SUB70432
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
MERCK INDEX
M3195
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
DRUG BANK
DB00671
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
CAS
79350-37-1
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
PUBCHEM
5362065
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
RXCUI
1546021
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY RxNorm
INN
5678
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY