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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:07 UTC
HMDB IDHMDB0014675
Secondary Accession Numbers
  • HMDB14675
Metabolite Identification
Common NameCefdinir
DescriptionCefdinir, also known as CFDN or omnicef, belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. Cefdinir is a very strong basic compound (based on its pKa). This drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug. Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. Oral LD50 of cefdinir in the rat is >2000 mg/kg. Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. Cefdinir is a bacteriostatic agent that treats bacterial infections by interfering with cell wall synthesis.
Structure
Data?1582753207
Synonyms
ValueSource
(6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
(6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefdinirumChEBI
CFDNChEBI
CefzonKegg
OmnicefKegg
(6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
CefdirnirHMDB
Abbott brand OF cefdinirHMDB
7-(2 (2-Aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acidHMDB
Chemical FormulaC14H13N5O5S2
Average Molecular Weight395.414
Monoisotopic Molecular Weight395.035809931
IUPAC Name(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Nameomnicef
CAS Registry Number91832-40-5
SMILES
[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O
InChI Identifier
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
InChI KeyRTXOFQZKPXMALH-GHXIOONMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • 1,3-thiazol-2-amine
  • Azole
  • Ketoxime
  • Tertiary carboxylic acid amide
  • Thiazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Amino acid
  • Thioether
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.088 g/LNot Available
LogP-0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP0.02ALOGPS
logP-1.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.34 m³·mol⁻¹ChemAxon
Polarizability36.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4922000000-dc82c787eb5267828736Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-8912300000-c4af10b287884f316c7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-2983000000-72bf1ac3398fbaa1531bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-2983000000-72bf1ac3398fbaa1531bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-3986000000-29ff02cc01fe7ad5cf7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i1-5931000000-530ddcf0eb776ea863d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aba-9310000000-6b26289821c95ff831b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0395000000-7d34c89c2566c38ee6d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1942000000-fa07a7e2149c3ada059fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b9cfff965d6914b74511Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00535 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00535 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00535
Phenol Explorer Compound IDNot Available
FooDB IDFDB009424
KNApSAcK IDNot Available
Chemspider ID5291705
KEGG Compound IDC08110
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefdinir
METLIN IDNot Available
PubChem Compound6915944
PDB IDNot Available
ChEBI ID3485
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. [PubMed:1201739 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
  3. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]