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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:19:52 UTC
HMDB IDHMDB0014464
Secondary Accession Numbers
  • HMDB14464
Metabolite Identification
Common NamePiperacillin
DescriptionPiperacillin is only found in individuals that have used or taken this drug. It is a semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Piperacillin inhibits 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 Piperacillin interferes with an autolysin inhibitor.
Structure
Data?1582753183
Synonyms
ValueSource
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
Piperacillin anhydrousChEBI
PIPCKegg
PeracinKegg
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
AB piperacillinHMDB
Fresenius brand OF piperacillin sodiumHMDB
PipcilHMDB
Piperacillin freseniusHMDB
Piperacillin monosodium saltHMDB
Piperacillin sodiumHMDB
Piperacillin curasanHMDB
Sodium, piperacillinHMDB
Pipera hamelnHMDB
Piperacillin hexalHMDB
PipracilHMDB
Astrapin brand OF piperacillin sodiumHMDB
Hexal brand OF piperacillin sodiumHMDB
Monosodium salt, piperacillinHMDB
PipercillinHMDB
Salt, piperacillin monosodiumHMDB
Wyeth brand OF piperacillin sodiumHMDB
Curasan brand OF piperacillin sodiumHMDB
AB-piperacillinHMDB
AHP brand OF piperacillin sodiumHMDB
Lederle brand OF pipracillin sodiumHMDB
Pipera-hamelnHMDB
Piperacillin ratiopharmHMDB
Piperacillin-ratiopharmHMDB
PiprilHMDB
Ratiopharm brand OF piperacillin sodiumHMDB
Curasan, piperacillinHMDB
Chemical FormulaC23H27N5O7S
Average Molecular Weight517.555
Monoisotopic Molecular Weight517.163118933
IUPAC Name(2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namepiperacillin
CAS Registry Number66258-76-2
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
InChI KeyIVBHGBMCVLDMKU-GXNBUGAJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Piperazine-1-carboxamide
  • Dioxopiperazine
  • Penam
  • N-alkylpiperazine
  • Ureide
  • N-acyl urea
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Piperazine
  • Beta-lactam
  • Dicarboximide
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Urea
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Carbonic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Thioether
  • Hemithioaminal
  • Carboxylic acid
  • Dialkylthioether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP0.3Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available223.047http://allccs.zhulab.cn/database/detail?ID=AllCCS00001509
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(0.67) g/LALOGPS
logP10(-0.26) g/LChemAxon
logS10(-3.6) g/LALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.3 m³·mol⁻¹ChemAxon
Polarizability51.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+217.67331661259
DarkChem[M-H]-214.58831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piperacillin,1TMS,#1CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)C2=CC=CC=C2)C(=O)C1=O3905.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Piperacillin,1TMS,#2CCN1CCN(C(=O)N[C@@H](C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C)C2=CC=CC=C2)C(=O)C1=O3871.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Piperacillin,1TMS,#3CCN1CCN(C(=O)N([C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)C2=CC=CC=C2)[Si](C)(C)C)C(=O)C1=O3771.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Piperacillin,1TBDMS,#1CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)C2=CC=CC=C2)C(=O)C1=O4116.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Piperacillin,1TBDMS,#2CCN1CCN(C(=O)N[C@@H](C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2)C(=O)C1=O4075.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Piperacillin,1TBDMS,#3CCN1CCN(C(=O)N([C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C(=O)C1=O3996.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00319 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00319 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00319
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID39798
KEGG Compound IDC14034
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperacillin
METLIN IDNot Available
PubChem Compound43672
PDB IDNot Available
ChEBI ID8232
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. Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection. Antimicrob Agents Chemother. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. [PubMed:16940077 ]

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 ]