Cefadroxil (CED0005893)

Record Information
Version1.0
Creation Date2016-05-22 03:38:24 UTC
Update Date2026-08-19 15:41:45 UTC
Accession NumberCHEM016610
Identification
Common NameCefadroxil
ClassSmall Molecule
Description
Cefadroxil is an organic compound with the formula C16H17N3O5S and an average molecular weight of 363.39 g/mol. Cefadroxil belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. The substance is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically within the categories of antibiotics and beta-lactam antibacterials. Recorded exposure routes for the compound include oral and inhalation. Cefadroxil acts on four recorded protein targets: Penicillin-binding protein 1A (pbpA), Penicillin-binding protein 1b (pbp1b), Penicillin-binding protein 2B (penA), and it serves as an inhibitor of serine-type D-Ala-D-Ala carboxypeptidase (pbp3).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CDXChEBI
Cefadroxil anhydrousChEBI
CefadroxiloChEBI
CefadroxilumChEBI
CephadroxilChEBI
D-CefadroxilChEBI
SumacefKegg
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
Cefadroxil monohydrateHMDB
CefradroxilHMDB
4-HydroxycephalexinHMDB
Anhydrous, cefadroxilHMDB
BL S 578HMDB
BL S578HMDB
BL-S578HMDB
BidocefHMDB
4 HydroxycephalexinHMDB
BL-S 578HMDB
BLS 578HMDB
CephadroxylHMDB
DuricefHMDB
Monohydrate, cefadroxilHMDB
UltracefHMDB
Chemical FormulaC16H17N3O5S
Average Molecular Mass363.388 g/mol
Monoisotopic Mass363.089 g/mol
CAS Registry Number50370-12-2
IUPAC Name(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecephadroxil
SMILES[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
InChI KeyBOEGTKLJZSQCCD-UEKVPHQBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassDibenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP0.51ALOGPS
logP-2.4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.95 m³·mol⁻¹ChemAxon
Polarizability35.86 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-1900000000-97d0bd980cf80d56d1d2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-0900000000-e43e7eb2ba5596d04ec6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1933000000-b1999d677c51baddfa90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-2920000000-d9fa5e68a9d8b3bbdb64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9600000000-6276612d64e8c9ff00c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0294000000-15be7a5887c970b07ff9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-3893000000-8b06619ab1def238f166Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9710000000-b4c3a1680bc6e2cf0111Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0209000000-b75b7367908a0d7b6ea4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6w-0913000000-3e844219a6f26aed36cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ej-2900000000-1748910365af881e2274Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08pi-0039000000-6e6d4b433dfcbfc5c1a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08gi-1917000000-88044cc0168626b32d3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0596-5900000000-b29d2d55b72fa58a3bc0Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6863.0Log mg/kg[3900:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Cefadroxil Drug Metabolism Action Pathway
Cefadroxil Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.0778492
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)12.4559
Solute carrier family 15 member 2 structureClick to view 3D structureSolute carrier family 15 member 2Q16348HumansPredicted (SEA)2.41333
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)0.311397
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.700643
Click to view 3D structureSolute carrier family 15 member 2Q63424Rattus norvegicusPredicted (SEA)0.0778492
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)7.86277
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.622794
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.622794
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)201.24
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)1228.85
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)1407.2
Click to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)519.566
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)637.819
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)631.746
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)750.233
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)379.359
Glutamate receptor ionotropic, NMDA 2B structureClick to view 3D structureGlutamate receptor ionotropic, NMDA 2BQ13224HumansPredicted (SEA)289.755
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)2151.91
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)1199.89
Click to view 3D structureSigma intracellular receptor 2Q5U3Y7Rattus norvegicusPredicted (SEA)767.126
Click to view 3D structureKappa-type opioid receptorP41144Cavia porcellusPredicted (SEA)894.41
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)352.034
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)1974.65
Concentrations
Not Available
External Links
DrugBank IDDB01140
HMDB IDHMDB0015271
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCefadroxil
Chemspider ID43630
ChEBI ID3479
PubChem Compound ID47965
Kegg Compound IDC06878
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21425867
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23224978
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23959853
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24080658
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24412692
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24667741
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9131470