Carbenicillin (CHEM022140)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:21:24 UTC
Update Date2026-04-13 20:33:36 UTC
Accession NumberCHEM022140
Identification
Common NameCarbenicillin
ClassSmall Molecule
DescriptionBroad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
alpha-CarboxybenzylpencillinChEBI
alpha-Phenyl(carboxymethylpenicillin)ChEBI
CarbenicilinaChEBI
CarbenicillineChEBI
CarbenicillinumChEBI
CarboxybenzylpenicillinChEBI
CBPCChEBI
N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acidChEBI
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
a-CarboxybenzylpencillinGenerator
Α-carboxybenzylpencillinGenerator
a-Phenyl(carboxymethylpenicillin)Generator
Α-phenyl(carboxymethylpenicillin)Generator
N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamateGenerator
CarbenicillinaHMDB
Carboxybenzylpenicillin acidHMDB
Carbenicillin disodiumHMDB
Carboxybenzyl penicillinHMDB
CSL Brand OF carbenicillin disodium saltHMDB
AnabactylHMDB
CarbecinHMDB
PyopenHMDB
Sanfer brand OF carbenicillin disodium saltHMDB
CarbapenHMDB
Disodium, carbenicillinHMDB
GeopenHMDB
MicrocillinHMDB
Penicillin, carboxybenzylHMDB
Chemical FormulaC17H18N2O6S
Average Molecular Mass378.400 g/mol
Monoisotopic Mass378.089 g/mol
CAS Registry Number4697-36-3
IUPAC Name(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namecarbenicillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(O)=O)C1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1
InChI KeyFPPNZSSZRUTDAP-UWFZAAFLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Penam
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Benzenoid
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Azetidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Thioether
  • Dialkylthioether
  • Azacycle
  • Organoheterocyclic compound
  • Hemithioaminal
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP1.13ALOGPS
logP0.82ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area124.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.82 m³·mol⁻¹ChemAxon
Polarizability36.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9648000000-75c4ae9c8d8548759c79Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9140520000-aefc24b65ed14a02ce91Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0966000000-56d889866f801a27cb89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1931000000-24c01d2bf9d0134d9a66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-090c-4900000000-364bbcd7e261912c778fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0191000000-1497e6a0c0f2e9306904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0391000000-839d544138add6310f69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00au-9530000000-334ecf6f74fddc5663a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0329000000-341846c34b38e9871a9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-030r-0934000000-924f0e01f6dd182046fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-ef6772c39f12e10bab53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-0809000000-67bc1fa9d561319cf054Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9702000000-d92a4cd1340f684365f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-296df6c3a51bba6facb9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00578
HMDB IDHMDB0014717
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarbenicillin
Chemspider ID19599
ChEBI ID3393
PubChem Compound ID20824
Kegg Compound IDC06869
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22648337
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6176550