C04

(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Created: 2013-05-13
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count45
Chiral Atom Count2
Bond Count47
Aromatic Bond Count5
2D diagram of C04
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Chemical Component Summary

Name(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SynonymsCefixime
Systematic Name (OpenEye OEToolkits)(6R,7R)-7-[[(2Z)-2-(2-azanyl-1,3-thiazol-4-yl)-2-(2-hydroxy-2-oxoethyloxyimino)ethanoyl]amino]-3-ethenyl-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC16 H15 N5 O7 S2
Molecular Weight453.45
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(O)CO\N=C(\c1nc(sc1)N)C(=O)NC3C(=O)N2C(=C(\C=C)CSC23)C(=O)O
SMILESCACTVS3.370Nc1scc(n1)C(=NOCC(O)=O)C(=O)N[CH]2[CH]3SCC(=C(N3C2=O)C(O)=O)C=C
SMILESOpenEye OEToolkits1.7.6C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)c3csc(n3)N)SC1)C(=O)O
Canonical SMILESCACTVS3.370 Nc1scc(n1)C(=N/OCC(O)=O)/C(=O)N[C@H]2[C@H]3SCC(=C(N3C2=O)C(O)=O)C=C
Canonical SMILESOpenEye OEToolkits1.7.6 C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/c3csc(n3)N)SC1)C(=O)O
InChIInChI1.03 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
InChIKeyInChI1.03 OKBVVJOGVLARMR-QSWIMTSFSA-N

Drug Info: DrugBank

DrugBank IDDB00671 
NameCefixime
Groups
  • approved
  • investigational
DescriptionBacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs).[A232920] β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death.[A232920, A232925, A232930] Cefixime is a broad-spectrum antibiotic and an orally-active third-generation semisynthetic cephalosporin.[A262894,A263011 ,L49293] Cephalosporins are beta-lactam antibiotics and can be used to treat gram-positive and gram-negative bacterial infections which include conditions such as skin infections, resistant bacteria, and meningitis.[A262995] Examples of third-generation cephalosporins are [ceftriaxone], [cefotaxime], and [ceftazidime].[A262995] Third-generation cephalosporins are often a first-line therapy against certain bacterial infections.[A263026] However, cefixime is not recommended as a first-line of treatment for uncomplicated urogenital, anorectal, or pharyngeal gonorrhea because cefixime does not provide the same bactericidal effect as [ceftriaxone].[L49686,A263021] Generally, cefixime is used to treat uurinary tract infections, middle ear infections, pharyngitis, tonsillitis, exacerbations of chronic bronchitis, and uncomplicated gonorrhea.[L49293] The beta-lactam ring of cefixime inhibits bacterial cell wall synthesis by binding to the penicillin-binding proteins which will then result in lysis.[A262995,A262945,A262950] Specifically, cephalosporins inhibit penicillin-sensitive enzymes responsible for the final 3D structure of the bacterial cell wall which in turn inhibit bacterial cell wall peptidoglycan synthesis.[T894, T322] Additionally, third-generation cephalosporins have been shown to have more stability in the presence of beta-lactamases compared to first- and second-generation cephalosporins.[A263031] Cefixime was first approved in the United States in 1986.[L49293]
Synonyms
  • Cefixime trihydrate
  • Cefixime anhydrous
  • Céfixime
  • Cefiximum
  • Cefixim
Brand Names
  • Suprax
  • Suprax - Tab 200mg
  • Auro-cefixime
  • Cefixime
  • Cefixime 400 mg UD
IndicationCefixime is indicated for the treatment of uncomplicated urinary tract infections caused by _Escherichia coli_ and _Proteus mirabilis_, otitis media caused by _Haemophilus influenzae_, _Moraxella catarrhalis_, and _Streptococcus pyogenes_, pharyngitis and tonsillitis caused by _Streptococcus pyogenes_, acute exacerbations of chronic bronchitis caused by _Streptococcus pneumoniae_ and _Haemophilus influenzae_, and uncomplicated gonorrhea (cervical/urethral) caused by _Neisseria gonorrhoeae_ (penicillinase-and non-penicillinase-producing isolates).[L49293]
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • J01DD08
  • J01RA16
  • J01RA15
CAS number79350-37-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 2MNLKKFFNTPTHEPFRDKKAERNLFARRTLVAFLGILLLTGVLFTNIYQL...unknowninhibitor
Penicillin-binding proteinMNTIFSARIMKRLALTTALCTAFISAAHADDLNIKTMIPGVPQIDAESYI...unknownbinder
Solute carrier family 22 member 5MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...unknowninhibitor
Solute carrier family 15 member 1MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...unknownsubstrate,inhibitor
Solute carrier family 15 member 2MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5362065
ChEMBL CHEMBL1541
ChEBI CHEBI:472657