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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:09:50 UTC
HMDB IDHMDB0014717
Secondary Accession Numbers
  • HMDB14717
Metabolite Identification
Common NameCarbenicillin
DescriptionCarbenicillin is only found in individuals that have used or taken this drug. It is a broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]Free carbenicillin is the predominant pharmacologically active fraction of the salt. Carbenicillin exerts its antibacterial activity by interference with final cell wall synthesis of susceptible bacteria. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that carbenicillin interferes with an autolysin inhibitor.
Structure
Thumb
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 disodiumMeSH
Carboxybenzyl penicillinMeSH
CSL Brand OF carbenicillin disodium saltMeSH
AnabactylMeSH
CarbecinMeSH
PyopenMeSH
Sanfer brand OF carbenicillin disodium saltMeSH
CarbapenMeSH
Disodium, carbenicillinMeSH
GeopenMeSH
MicrocillinMeSH
Penicillin, carboxybenzylMeSH
Chemical FormulaC17H18N2O6S
Average Molecular Weight378.4
Monoisotopic Molecular Weight378.088557008
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
CAS Registry Number4697-36-3
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 Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.39 g/LNot Available
LogP1.8Not 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9648000000-75c4ae9c8d8548759c79View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9140520000-aefc24b65ed14a02ce91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0966000000-56d889866f801a27cb89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1931000000-24c01d2bf9d0134d9a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-090c-4900000000-364bbcd7e261912c778fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0191000000-1497e6a0c0f2e9306904View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0391000000-839d544138add6310f69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00au-9530000000-334ecf6f74fddc5663a6View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00578 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00578 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00578
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19599
KEGG Compound IDC06869
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbenicillin
METLIN IDNot Available
PubChem Compound20824
PDB IDNot Available
ChEBI ID3393
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
References
  1. Sugatani J, Saito K, Honjo I: In vitro actions of some antibiotics on phospholipases. J Antibiot (Tokyo). 1979 Jul;32(7):734-9. [PubMed:541266 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]