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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:48 UTC
HMDB IDHMDB0015540
Secondary Accession Numbers
  • HMDB15540
Metabolite Identification
Common NameBacampicillin
DescriptionBacampicillin, also known as penglobe or BAPC, belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1]. Bacampicillin is a drug which is used for infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: gram-positive: streptococci (including s. faecalis and s. pneumoniae) and nonpenicillinase-producing staphylococci; gram-negative: h. influenzae, n. gonorrhoeae, e. coli, p. mirabilis, salmonellae and shigellae. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc. Bacampicillin is a very strong basic compound (based on its pKa). Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.
Structure
Data?1582753308
Synonyms
ValueSource
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanateChEBI
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateChEBI
BacampicilinaChEBI
BacampicillineChEBI
BacampicillinumChEBI
BAPCKegg
PenglobeKegg
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanic acidGenerator
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidGenerator
Bacampicillin hydrochlorideHMDB
Bacampicillin monohydrochlorideHMDB
Ethoxycarbonyloxyethyl ester OF ampicillinHMDB
BacampicineHMDB
CarampicillinHMDB
Chemical FormulaC21H27N3O7S
Average Molecular Weight465.52
Monoisotopic Molecular Weight465.156970923
IUPAC Name1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Traditional Namebacampicillin
CAS Registry Number50972-17-3
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC
InChI Identifier
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI KeyPFOLLRNADZZWEX-FFGRCDKISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Carbonic acid diester
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carbonic acid derivative
  • Carboxamide group
  • Carboxylic acid ester
  • Hemithioaminal
  • Thioether
  • Dialkylthioether
  • Azacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen 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 Solubility0.12 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.17ALOGPS
logP1.47ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area137.26 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.76 m³·mol⁻¹ChemAxon
Polarizability46.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-210a80ea99d7d8b19c7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-5914100000-b2bb79f625d3a39bd072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-7911000000-c5d3cfc8023d3a8d1c16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6910000000-bb9f92cfef936fcb5cabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0391100000-56ef32146ff2caf816afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8593000000-92004702bfb034e6fad9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9510000000-079171b8e9ca83a521cbSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01602 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01602 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01602
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390135
KEGG Compound IDC08122
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBacampicillin
METLIN IDNot Available
PubChem Compound441397
PDB IDNot Available
ChEBI ID2968
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available