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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:43:57 UTC
Update Date2022-03-07 02:57:12 UTC
HMDB IDHMDB0041851
Secondary Accession Numbers
  • HMDB41851
Metabolite Identification
Common NameCefpimizole
DescriptionCefpimizole is an antibiotic that belongs to the class of compounds known as cephalosporins (PMID: 3312705 ). Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to an oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. It is an anti-bacterial agent used in the treatment of uncomplicated genital or rectal infections (PMID: 3041630 ). Cefpimizole is also used to treat urethral infections caused by penicillinase-producing Neisseria gonorrhea (PPNG) (PMID: 6270834 ). It shows significant antibacterial activity against Pseudomonas aeruginosa, most members of the family Enterobacteriaceae, most Staphylococcus species, non-enterococcal Streptococcus species, Haemophilus influenzae, and Neisseria species (PMID: 4026275 ). It works by disrupting the synthesis of the peptidoglycan layer forming the bacterial cell wall. Cefpimizole is only found in individuals who have used or consumed this drug.
Structure
Data?1563863708
Synonyms
ValueSource
U-63196cefpimizoleHMDB
AC 1370HMDB
Cefpimizole sodiumHMDB
CPIZHMDB
7 beta-D-alpha-(4(5)-Carboxyimidazole-5(4)-carboxamido)phenylacetamido-3-(4-beta-sulfoethylpyridinium)methyl-3-cephem-4-carboxylic acidHMDB
1-{[(6R,7R)-2-carboxy-7-{[(2R)-2-{[(5-carboxy-1H-imidazol-4-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-phenylethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-(2-sulphonatoethyl)pyridin-1-iumHMDB
CefpimizoleMeSH
Chemical FormulaC28H26N6O10S2
Average Molecular Weight670.67
Monoisotopic Molecular Weight670.115182462
IUPAC Name1-{[(6R,7R)-2-carboxy-7-{[(2R)-2-{[(5-carboxy-1H-imidazol-4-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-phenylethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-(2-sulfonatoethyl)pyridin-1-ium
Traditional Name1-{[(6R,7R)-2-carboxy-7-{[(2R)-2-{[(5-carboxy-1H-imidazol-4-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-phenylethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-(2-sulfonatoethyl)pyridin-1-ium
CAS Registry Number84880-03-5
SMILES
[H][C@](N=C(O)C1=C(NC=N1)C(O)=O)(C(O)=N[C@]1([H])C(=O)N2C(C(O)=O)=C(C[N+]3=CC=C(CCS([O-])(=O)=O)C=C3)CS[C@]12[H])C1=CC=CC=C1
InChI Identifier
InChI=1S/C28H26N6O10S2/c35-23(18(16-4-2-1-3-5-16)31-24(36)19-20(27(38)39)30-14-29-19)32-21-25(37)34-22(28(40)41)17(13-45-26(21)34)12-33-9-6-15(7-10-33)8-11-46(42,43)44/h1-7,9-10,14,18,21,26H,8,11-13H2,(H5-,29,30,31,32,35,36,38,39,40,41,42,43,44)/t18-,21-,26-/m1/s1
InChI KeyLNZMRLHZGOBKAN-KAWPREARSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Cephem
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Meta-thiazine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Pyridinium
  • Benzenoid
  • Alkanesulfonic acid
  • Vinylogous amide
  • Azole
  • Beta-lactam
  • Heteroaromatic compound
  • Imidazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Tertiary carboxylic acid amide
  • Lactam
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Thioether
  • Dialkylthioether
  • Azacycle
  • Hemithioaminal
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic zwitterion
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID61863
KEGG Compound IDC13024
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefpimizole
METLIN IDNot Available
PubChem Compound68597
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hara K, Shimada J: [New antimicrobial agent series XXI: Cefpimizole]. Jpn J Antibiot. 1987 Jun;40(6):1108-22. [PubMed:3312705 ]
  2. Raad II, Sherertz RJ, Loveless MO, Carillo C, O'Connor RP, Miller M, Mostow SR: Comparison of cefpimizole with cefotaxime and penicillin G for treatment of uncomplicated gonorrhea. Sex Transm Dis. 1988 Apr-Jun;15(2):73-7. doi: 10.1097/00007435-198804000-00001. [PubMed:3041630 ]
  3. Handsfield HH, Holmes KK: Treatment of uncomplicated gonorrhea with cefotaxime. Sex Transm Dis. 1981 Jul-Sep;8(3):187-91. doi: 10.1097/00007435-198107000-00003. [PubMed:6270834 ]
  4. Jones RN, Ayers LW, Gavan TL, Gerlach EH, Sommers HM: In vitro comparative antimicrobial activity of cefpimizole against clinical isolates from five medical centers. Antimicrob Agents Chemother. 1985 Jun;27(6):982-4. doi: 10.1128/aac.27.6.982. [PubMed:4026275 ]