Pivampicillin (CHEM018331)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:09:43 UTC
Update Date2016-11-09 01:15:46 UTC
Accession NumberCHEM018331
Identification
Common NamePivampicillin
ClassSmall Molecule
DescriptionA penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass463.547 g/mol
Monoisotopic Mass463.178 g/mol
CAS Registry Number33817-20-8
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
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 IdentifierInChI=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
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 Solubility0.035 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-459356a4997f59da0598Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pi0-1922100000-c66d44e9e103153e78e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4921000000-e513d7e709a4cc359313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9800000000-1d45b7913c48a4570128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290100000-8fa5f97dea1c97508c9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1691100000-3c1b28211f3589a2e3b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ke9-9630000000-8cb9ef389fad4dc01d14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0322900000-3504b69e69554572682bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7954200000-eb67af5b14cd5f26d30bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5901000000-f16b60a416509c0adb29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-1329700000-2f3c07f08b5464f78950Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-4934000000-ae133ff906d357093abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-a556e0bfb78074f98c8dSpectrum
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 IDDB01604
HMDB IDHMDB0015542
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPivampicillin
Chemspider ID30899
ChEBI ID8255
PubChem Compound ID33478
Kegg Compound IDC11750
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10830765
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15793098
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21144541
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3465515
6. 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.
7. 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.