Loracarbef (CED0012215)

Record Information
Version1.0
Creation Date2016-05-25 18:20:30 UTC
Update Date2026-08-19 15:19:45 UTC
Accession NumberCHEM022109
Identification
Common NameLoracarbef
ClassSmall Molecule
Description
Loracarbef is an organic compound with the chemical formula C16H16ClN3O4 and an average molecular weight of 349.77 g/mol. Loracarbef belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from four recorded sources, which include healthcare, pharmaceuticals & veterinary products as beta-lactam antibacterials, electrical & electronic equipment such as video games and emergency protective devices, and household cleaning & consumer products specifically other smoking requisites. The recorded route of exposure for this substance is oral. In terms of biological activity, loracarbef has two recorded protein targets: it acts as an inhibitor of penicillin-binding protein 1A (pbpA) and serine-type D-Ala-D-Ala carboxypeptidase (pbp3).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LORACABEFChEBI
LoracarbefumChEBI
CarbacHMDB
Lilly brand OF loracarbef monohydrateHMDB
LorafemHMDB
LoraxHMDB
Monarch brand OF loracarbef monohydrateHMDB
Zambon brand OF loracarbef monohydrateHMDB
LorabidHMDB
Lilly brand OF loracarbefHMDB
Syntex brand OF loracarbef monohydrateHMDB
Loracarbef monohydrateHMDB
Chemical FormulaC16H16ClN3O4
Average Molecular Mass349.769 g/mol
Monoisotopic Mass349.083 g/mol
CAS Registry Number76470-66-1
IUPAC Name(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Nameloracabef
SMILESN[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1
InChI KeyJAPHQRWPEGVNBT-UTUOFQBUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbacephems. These are a new class of beta-lactam antibiotics similar in structure to the cephalosporins. They differ from cephalosporins, however, in the substitution of a sulfur atom in the dihydrothiazine ring with a methylene group to form a tetrahydropyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCarbacephems
Alternative Parents
Substituents
  • Carbacephem
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Tetrahydropyridine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Vinylogous halide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Haloalkene
  • Chloroalkene
  • Vinyl halide
  • Vinyl chloride
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organohalogen compound
  • Organochloride
  • Amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary 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 Solubility0.32 g/LALOGPS
logP0.55ALOGPS
logP-2.4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.64 m³·mol⁻¹ChemAxon
Polarizability32.61 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 Spectrumsplash10-0a4i-8901000000-9624c4237beed0fc58b1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-6911000000-1942c1bc1b579dcb17ffNot 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 Spectrumsplash10-0pvi-0946000000-df5d2ead7c26276f85f9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-1930000000-9d4196e112fdc37ad21bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4900000000-57e592b2ff0c830fc344Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0319000000-e45ecb0b8853bd1bf498Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-1901000000-ffe4f565f43063b475b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6u-8900000000-e8d02c2084b2878efcdaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-b7a3c9f8668fbd31bcdeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uea-8916000000-63309ef2348514c74998Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9210000000-df0fe7334b3e12739576Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0109000000-ab09a95a465c7b11929fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0619000000-7bcf73b1d7af848563dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4921000000-9eb7cf6e6a3cb01d371dNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H 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
5353.0Log mg/kg[3000:9500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
Pathways
1 pathway
Loracarbef Drug Metabolism Action Pathway
Loracarbef Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
E3 ubiquitin-protein ligase XIAP structureClick to view 3D structureE3 ubiquitin-protein ligase XIAPP98170HumansPredicted (SEA)56.7521
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)2.33548
Click to view 3D structureSolute carrier family 15 member 2Q63424Rattus norvegicusPredicted (SEA)8.71911
Click to view 3D structureMelanocortin receptor 5G7PWB2Macaca fascicularisPredicted (SEA)25.7681
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)1697.97
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)1481.39
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)1.55698
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)1778.54
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)1690.11
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)609.949
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)4066.84
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)1519.07
Histone deacetylase 4 structureClick to view 3D structureHistone deacetylase 4P56524HumansPredicted (SEA)1109.9
Click to view 3D structureProcathepsin LP07154Rattus norvegicusPredicted (SEA)77.8492
Solute carrier family 15 member 2 structureClick to view 3D structureSolute carrier family 15 member 2Q16348HumansPredicted (SEA)86.1791
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)2626.55
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)670.827
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)2522.7
Cathepsin K structureClick to view 3D structureCathepsin KP43235HumansPredicted (SEA)638.13
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)56.4407
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)33.1638
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)3.42537
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)3.19182
Baculoviral IAP repeat-containing protein 8 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 8Q96P09HumansPredicted (SEA)8.95266
Baculoviral IAP repeat-containing protein 2 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 2Q13490HumansPredicted (SEA)17.2047
Concentrations
Not Available
External Links
DrugBank IDDB00447
HMDB IDHMDB0014590
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLoracarbef
Chemspider ID4447635
ChEBI ID47544
PubChem Compound ID5284585
Kegg Compound IDC08109
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1553350
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1621740
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1621742
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8453172
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9131470
7. Copper RD: The carbacephems: a new beta-lactam antibiotic class. Am J Med. 1992 Jun 22;92(6A):2S-6S.
8. Brogden RN, McTavish D: Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May;45(5):716-36.
9. Dantzig AH, Duckworth DC, Tabas LB: Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta. 1994 Apr 20;1191(1):7-13.
10. Force RW, Nahata MC: Loracarbef: a new orally administered carbacephem antibiotic. Ann Pharmacother. 1993 Mar;27(3):321-9.