WPP

Piperacillin

Created: 2011-01-06
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count63
Chiral Atom Count4
Bond Count66
Aromatic Bond Count6
2D diagram of WPP
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Chemical Component Summary

NamePiperacillin
Synonyms(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 acid
Systematic Name (OpenEye OEToolkits)(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxo-piperazin-1-yl)carbonylamino]-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC23 H27 N5 O7 S
Molecular Weight517.555
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C1C(=O)N(CC)CCN1C(=O)NC(c2ccccc2)C(=O)NC4C(=O)N3C(C(=O)O)C(SC34)(C)C
SMILESCACTVS3.370CCN1CCN(C(=O)N[CH](C(=O)N[CH]2[CH]3SC(C)(C)[CH](N3C2=O)C(O)=O)c4ccccc4)C(=O)C1=O
SMILESOpenEye OEToolkits1.7.0CCN1CCN(C(=O)C1=O)C(=O)NC(c2ccccc2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
Canonical SMILESCACTVS3.370 CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)c4ccccc4)C(=O)C1=O
Canonical SMILESOpenEye OEToolkits1.7.0 CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c2ccccc2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChIInChI1.03 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
InChIKeyInChI1.03 IVBHGBMCVLDMKU-GXNBUGAJSA-N

Drug Info: DrugBank

DrugBank IDDB00319 
NamePiperacillin
Groups approved
DescriptionSemisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics.
Synonyms
  • (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 acid
  • Piperacillin
  • Pipéracilline
  • Piperacillina
  • Piperacillin sodium
Brand Names
  • Pipracil Inj 2gm/vial
  • Vpi-piperacillin and Tazobactam for Injection
  • Pipracil Pharmacy Bulk Vial-pws IV 40g/vial
  • Tazocin
  • PIPERACILLIN SODIUM and TAZOBACTAM SODIUM
IndicationFor the treatment of polymicrobial infections.
Categories
  • Agents that produce neuromuscular block (indirect)
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • J01CR50
  • J01CA12
CAS number66258-76-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 3MKKIFLTLLTVSLLGGASTAVAQDFTIAAKHAIAVEANTGKILYEKDATQ...unknowninhibitor
Penicillin-binding protein 2BMRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASAS...unknowninhibitor
Penicillin-binding protein 2aMKLDKLFEKFLSLFKKETSELEDSDSTILRRSRSDRKKLAQVGPIRKFWR...unknowninhibitor
Penicillin-binding protein 1bMQNQLNELKRKMLEFFQQKQKNKKSARPGKKGSSTKKSKTLDKSAIFPAI...unknowninhibitor
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 43672
ChEMBL CHEMBL702
ChEBI CHEBI:8232