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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015542
Secondary Accession Numbers
  • HMDB15542
Metabolite Identification
Common NamePivampicillin
DescriptionPivampicillin, also known as pondocillin or berocillin, belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group. Based on a literature review a significant number of articles have been published on Pivampicillin.
Structure
Data?1582753308
Synonyms
ValueSource
Ampicillin pivaloyloxymethyl esterChEBI
Pivaloyloxymethyl ampicillinateChEBI
PivampicilinaChEBI
PivampicillineChEBI
PivampicillinumChEBI
PondocillinKegg
Pivaloyloxymethyl ampicillinic acidGenerator
PivaloylampicillinHMDB
BerocillinHMDB
Serra pamies brand OF pivampicillin hydrochlorideHMDB
Pivampicillin hydrochlorideHMDB
Ampicillin pivaloyl esterHMDB
Ester, ampicillin pivaloylHMDB
Hydrochloride, pivampicillinHMDB
Leo brand OF pivampicillinHMDB
Monohydrochloride, pivampicillinHMDB
PivamiserHMDB
Pivampicillin monohydrochlorideHMDB
Chemical FormulaC22H29N3O6S
Average Molecular Weight463.547
Monoisotopic Molecular Weight463.177706365
IUPAC Name[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
Traditional Namepivampicillin
CAS Registry Number33817-20-8
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C
InChI Identifier
InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1
InChI KeyZEMIJUDPLILVNQ-ZXFNITATSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTriazoles
Direct ParentPhenyl-1,2,4-triazoles
Alternative Parents
Substituents
  • Phenyl-1,2,4-triazole
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.035 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP1.43ALOGPS
logP2.07ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area128.03 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.25 m³·mol⁻¹ChemAxon
Polarizability47.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.90831661259
DarkChem[M-H]-196.68531661259
DeepCCS[M-2H]-249.10730932474
DeepCCS[M+Na]+223.53930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pivampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C3855.8Standard polar33892256
Pivampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C2819.3Standard non polar33892256
Pivampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C3269.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pivampicillin,1TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3148.3Semi standard non polar33892256
Pivampicillin,1TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3024.6Standard non polar33892256
Pivampicillin,1TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C4483.4Standard polar33892256
Pivampicillin,1TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3070.1Semi standard non polar33892256
Pivampicillin,1TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3002.8Standard non polar33892256
Pivampicillin,1TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C4659.9Standard polar33892256
Pivampicillin,2TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3128.5Semi standard non polar33892256
Pivampicillin,2TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3094.6Standard non polar33892256
Pivampicillin,2TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C4020.6Standard polar33892256
Pivampicillin,2TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3172.8Semi standard non polar33892256
Pivampicillin,2TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3156.8Standard non polar33892256
Pivampicillin,2TMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C4223.9Standard polar33892256
Pivampicillin,3TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3206.2Semi standard non polar33892256
Pivampicillin,3TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3230.3Standard non polar33892256
Pivampicillin,3TMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3813.4Standard polar33892256
Pivampicillin,1TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3341.8Semi standard non polar33892256
Pivampicillin,1TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3234.0Standard non polar33892256
Pivampicillin,1TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C4501.0Standard polar33892256
Pivampicillin,1TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3290.8Semi standard non polar33892256
Pivampicillin,1TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3203.8Standard non polar33892256
Pivampicillin,1TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4663.9Standard polar33892256
Pivampicillin,2TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3465.3Semi standard non polar33892256
Pivampicillin,2TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3487.0Standard non polar33892256
Pivampicillin,2TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4162.3Standard polar33892256
Pivampicillin,2TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3599.4Semi standard non polar33892256
Pivampicillin,2TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3517.8Standard non polar33892256
Pivampicillin,2TBDMS,isomer #2CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4292.2Standard polar33892256
Pivampicillin,3TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3764.6Semi standard non polar33892256
Pivampicillin,3TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3780.2Standard non polar33892256
Pivampicillin,3TBDMS,isomer #1CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4005.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pivampicillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-459356a4997f59da05982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivampicillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivampicillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 10V, Positive-QTOFsplash10-0pi0-1922100000-c66d44e9e103153e78e72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 20V, Positive-QTOFsplash10-0a4i-4921000000-e513d7e709a4cc3593132016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 40V, Positive-QTOFsplash10-0a4i-9800000000-1d45b7913c48a45701282016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 10V, Negative-QTOFsplash10-0a4i-0290100000-8fa5f97dea1c97508c9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 20V, Negative-QTOFsplash10-0a4i-1691100000-3c1b28211f3589a2e3b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 40V, Negative-QTOFsplash10-0ke9-9630000000-8cb9ef389fad4dc01d142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 10V, Positive-QTOFsplash10-01ot-0322900000-3504b69e69554572682b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 20V, Positive-QTOFsplash10-0a4i-7954200000-eb67af5b14cd5f26d30b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 40V, Positive-QTOFsplash10-0a4i-5901000000-f16b60a416509c0adb292021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 10V, Negative-QTOFsplash10-01t9-1329700000-2f3c07f08b5464f789502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 20V, Negative-QTOFsplash10-0udl-4934000000-ae133ff906d357093abb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivampicillin 40V, Negative-QTOFsplash10-0006-9220000000-a556e0bfb78074f98c8d2021-10-11Wishart LabView Spectrum
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 DB01604 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01604 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01604
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30899
KEGG Compound IDC11750
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivampicillin
METLIN IDNot Available
PubChem Compound33478
PDB IDNot Available
ChEBI ID8255
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [PubMed:15793098 ]
  2. Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. doi: 10.1111/j.1532-5415.2010.02741.x. [PubMed:20398122 ]