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Record Information
Version2.0
Created at2024-09-11 07:14:34 UTC
Updated at2024-09-11 07:14:35 UTC
NP-MRD IDNP0336649
Secondary Accession NumbersNone
Natural Product Identification
Common NameCeftiofur
DescriptionCeftiofur 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. Ceftiofur was first documented in 2024 (PMID: 39265834). Based on a literature review a small amount of articles have been published on Ceftiofur (PMID: 39240080) (PMID: 39217040) (PMID: 39155341) (PMID: 39134329).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H17N5O7S3
Average Mass523.5500 Da
Monoisotopic Mass523.02901 Da
IUPAC Name7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Name7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CO\N=C(/C(=O)NC1C2SCC(CSC(=O)C3=CC=CO3)=C(N2C1=O)C(O)=O)C1=CSC(N)=N1
InChI Identifier
InChI=1/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-
InChI KeyZBHXIWJRIFEVQY-KSEXSDGBNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These 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
  • Furoic acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • 1,3-thiazol-2-amine
  • Azole
  • Furan
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.11ChemAxon
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)3.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area177.42 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.51 m³·mol⁻¹ChemAxon
Polarizability50.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCeftiofur
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Vasco KA, Bowcutt B, Carbonell S, Souza L, Robison C, Abuelo A, Erskine R, Norby B, Zhang L, Ruegg PL, Manning SD: Selection of antibiotic-resistant bacterial populations in the dairy cow gut following intramuscular ceftiofur treatment for metritis. J Dairy Sci. 2024 Dec;107(12):11536-11549. doi: 10.3168/jds.2023-24572. Epub 2024 Sep 17. [PubMed:39265834 ]
  2. Gelalcha BD, Gelgie AE, Kerro Dego O: Antimicrobial resistance and prevalence of extended-spectrum beta-lactamase-producing Klebsiella species in East Tennessee dairy farms. Microbiol Spectr. 2024 Oct 3;12(10):e0353723. doi: 10.1128/spectrum.03537-23. Epub 2024 Sep 6. [PubMed:39240080 ]
  3. Zhao Y, Mao W, Liu B, Wang YF, Zhang SY, Guo LL, Qian YH, Gong ZG, Zhao JM, Yang XL, Qu GG, Hasi SR, Bai YT, Cao JS: Preparation of ceftiofur-encapsulated hen-egg low-density lipoproteins and their antibacterial effects on intracellular Staphylococcus aureus. Int J Biol Macromol. 2024 Oct;278(Pt 4):134840. doi: 10.1016/j.ijbiomac.2024.134840. Epub 2024 Aug 31. [PubMed:39217040 ]
  4. Veiga RF, Clarindo LN, Fensterseifer AL, Pompelli LH, Sfaciotte RAP, Schwarz DGG, Eloy LR, Ferraz SM: Prevalence and antimicrobial susceptibility of Streptococcus equi isolated from horses in Santa Catarina state, Southern Brazil. Braz J Microbiol. 2024 Aug 19;55(4):4147-55. doi: 10.1007/s42770-024-01479-8. [PubMed:39155341 ]
  5. Mzyk DA, Halleran JL, Sylvester HJ, Giles CB, Jacob ME, Baynes RE, Foster DM: Continuous sampling of healthy and mastitic quarters of lactating cattle by ultrafiltration after intramammary ceftiofur hydrochloride administration. J Vet Intern Med. 2024 Sep-Oct;38(5):2814-2822. doi: 10.1111/jvim.17155. Epub 2024 Aug 12. [PubMed:39134329 ]