piperacillin   Click here for help

GtoPdb Ligand ID: 10921

Synonyms: CL 227,193 | CL-227193 | PIPC | T-1220 | Tazocin® (piperacillin + tazobactam)
Approved drug PDB Ligand
piperacillin is an approved drug (FDA (1981), UK (2011))
Compound class: Synthetic organic
Comment: Piperacillin is a broad-spectrum semisynthetic, ampicillin-derived antibacterial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 181.73
Molecular weight 517.16
XLogP 0.33
No. Lipinski's rules broken 1
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Canonical SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1
Isomeric SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1
InChI 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), UK (2011))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4296 piperacillin
Synonyms Click here for help
CL 227,193 | CL-227193 | PIPC | T-1220 | Tazocin® (piperacillin + tazobactam)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Piperacillin
Other databases
BindingDB Ligand 50240426
CAS Registry No. 61477-96-1 (source: WHO INN record)
DrugBank Ligand DB00319
DrugCentral Ligand 2187
GtoPdb PubChem SID 405560362
PubChem CID 43672
Search Google for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N
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UniChem Compound Search for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N
UniChem Connectivity Search for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N