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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.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=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

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).
Name Type Language
CEFIXIME
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CEFIXIME [USP-RS]
Common Name English
CEFIXIME [EP]
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
CL-284635
Code English
FR 17027
Code English
CL 284,635
Code English
CEFIXIME [VANDF]
Common Name English
CEFIXIME [ORANGE BOOK]
Common Name English
CEFIXIME [USP]
Common Name English
CEFIXIME TRIHYDRATE [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 164
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
WHO-VATC QJ01DD08
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
WHO-ATC J01DD08
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
Code System Code Type Description
ChEMBL
CHEMBL1541
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
MERCK INDEX
M3195
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY Merck Index
RXCUI
25033
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY RxNorm
CAS
125110-14-7
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
WIKIPEDIA
CEFIXIME
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
EVMPD
SUB01116MIG
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
PUBCHEM
5491577
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB171326
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
MESH
D020682
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY
NCI_THESAURUS
C1100
Created by admin on Tue Mar 06 10:27:17 UTC 2018 , Edited by admin on Tue Mar 06 10:27:17 UTC 2018
PRIMARY