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

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

Molecular Formula C16H15N5O7S2
Molecular Weight 453.45
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
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)

Approval Year

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
Cefixime compared with amoxicillin for treatment of acute otitis media.
1991 Jul
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
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.
2004 Oct
IgE antibodies to betalactams: relationship between the triggering hapten and the specificity of the immune response.
2006 Aug
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

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
Created
by admin
on Tue Mar 06 10:41:44 UTC 2018
Edited
by admin
on Tue Mar 06 10:41:44 UTC 2018
Record UNII
XZ7BG04GJX
Record Status Validated (UNII)
Record Version
  • Download
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 Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
NDF-RT N0000175488
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
LIVERTOX 164
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
Code System Code Type Description
EVMPD
SUB07395MIG
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
EPA CompTox
79350-37-1
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
LactMed
79350-37-1
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
EVMPD
SUB70432
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
MERCK INDEX
M3195
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
DRUG BANK
DB00671
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
CAS
79350-37-1
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
PUBCHEM
5362065
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY SWITZERF
RXCUI
1546021
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY RxNorm
INN
5678
Created by admin on Tue Mar 06 10:41:44 UTC 2018 , Edited by admin on Tue Mar 06 10:41:44 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY