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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 IDHMDB0015543
Secondary Accession Numbers
  • HMDB15543
Metabolite Identification
Common NamePivmecillinam
DescriptionPivmecillinam is only found in individuals that have used or taken this drug. It is a mecillinam prodrug, a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [PubChem]Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins
Structure
Data?1582753308
Synonyms
ValueSource
[(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateChEBI
Amdinocillin pivoxilChEBI
Amdinocillin, pivaloyloxymethyl esterChEBI
PivmecilinamoChEBI
PivmecillinamumChEBI
[(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidGenerator
Leo brand OF pivmecillinam hydrochlorideHMDB
PivamdinocillinHMDB
Hydrochloride, pivmecillinamHMDB
Mecillinam pivaloyl esterHMDB
Pivmecillinam hydrochlorideHMDB
Pivaloyl ester, mecillinamHMDB
Pivoxil, amdinocillinHMDB
SelexidHMDB
Chemical FormulaC21H33N3O5S
Average Molecular Weight439.569
Monoisotopic Molecular Weight439.214091871
IUPAC Name[(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
Traditional Namepivmecilinamo
CAS Registry Number32886-97-8
SMILES
[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1
InChI Identifier
InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChI KeyNPGNOVNWUSPMDP-HLLBOEOZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Penam
  • Azepane
  • Acylal
  • Dicarboxylic acid or derivatives
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Azetidine
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Acetal
  • Amidine
  • Formamidine
  • Carboxylic acid amidine
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point119 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.053 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP3.23ALOGPS
logP2.91ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.66ChemAxon
pKa (Strongest Basic)7.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area88.51 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity113.03 m³·mol⁻¹ChemAxon
Polarizability47.7 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]+198.61731661259
DarkChem[M-H]-188.36131661259
DeepCCS[M-2H]-242.40530932474
DeepCCS[M+Na]+217.43130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pivmecillinam[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC13243.9Standard polar33892256
Pivmecillinam[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC12878.1Standard non polar33892256
Pivmecillinam[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC12923.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pivmecillinam GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9012000000-ea9d35d8c75e4246ab912017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivmecillinam 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 - Pivmecillinam 10V, Positive-QTOFsplash10-0lkc-0933100000-207d607d624521759c4a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 20V, Positive-QTOFsplash10-066r-2911000000-e698803b355747dc85ad2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 40V, Positive-QTOFsplash10-0a4i-9400000000-4c251e4b9870f1bb8e2e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 10V, Negative-QTOFsplash10-001i-0911000000-0118b6d73875ca106ecc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 20V, Negative-QTOFsplash10-001i-1931000000-ced5e83f734188289e152017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 40V, Negative-QTOFsplash10-00c0-9612000000-5d2b3043f240829637102017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 10V, Positive-QTOFsplash10-0006-0010900000-76b3918141d7d2d0d18c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 20V, Positive-QTOFsplash10-0a4r-5922100000-010f81553366b87ff5962021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 40V, Positive-QTOFsplash10-0cdi-3900000000-1058b7a1dbaa55f96dc32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 10V, Negative-QTOFsplash10-03fr-0033900000-bc636cd9795ad82fa7082021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 20V, Negative-QTOFsplash10-004j-3966200000-0506d8a084039adb337d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivmecillinam 40V, Negative-QTOFsplash10-00di-9653100000-76e29891ae64774b46572021-10-11Wishart 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 DB01605 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01605 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01605
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16735658
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivmecillinam
METLIN IDNot Available
PubChem Compound115163
PDB IDNot Available
ChEBI ID51210
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. Authors unspecified: Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. [PubMed:214285 ]
  2. Sjovall J, Huitfeldt B, Magni L, Nord CE: Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. [PubMed:3547627 ]
  3. Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [PubMed:14527775 ]