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
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
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
PubMed
Title | Date | PubMed |
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Double-blind comparison of cefixime and cefaclor in the treatment of acute otitis media in children. | 1991 |
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[Clinical evaluation of cefixime in pediatric respiratory tract infections]. | 1991 Jan |
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Cefixime compared with amoxicillin for treatment of acute otitis media. | 1991 Jul |
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5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. | 1995 |
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[Benign intracranial hypertension after treatment with pefloxacin]. | 1998 Aug |
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Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center. | 2004 Oct |
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IgE antibodies to betalactams: relationship between the triggering hapten and the specificity of the immune response. | 2006 Aug |
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The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. | 2007 Apr |
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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 |
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Diagnostic evaluation of hypersensitivity reactions to beta-lactam antibiotics in a large population of children. | 2014 Feb |
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Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J01DD08
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NDF-RT |
N0000175488
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LIVERTOX |
164
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NDF-RT |
N0000011161
Created by
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Code System | Code | Type | Description | ||
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SUB07395MIG
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79350-37-1
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79350-37-1
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SUB70432
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M3195
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DB00671
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79350-37-1
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5362065
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1546021
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PRIMARY | RxNorm | ||
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5678
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)