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 antibiotic.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
1. Griggs DJ, Peake L, Johnson MM, Ghori S, Mott A, Piddock LJ. (2009)
Beta-lactamase-mediated beta-lactam resistance in Campylobacter species: prevalence of Cj0299 (bla OXA-61) and evidence for a novel beta-Lactamase in C. jejuni.
Antimicrob Agents Chemother, 53 (8): 3357-64. [PMID:19506058]
2. National Collaborating Centre for Cancer. (2012)
National Institute for Health and Care Excellence: Guidance.
Neutropenic Sepsis: Prevention and Management of Neutropenic Sepsis in Cancer Patients,. [PMID:26065059]