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.

piperacillin is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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
InChI Key IVBHGBMCVLDMKU-GXNBUGAJSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Piperacillin (as the sodium salt) is used to treat moderate-to-severe infections due to susceptible organisms. In the UK, piperacillin is approved in a number of combination products with tazobactam, which are all administered intravenously (e.g. Tazocin). Tazocin is indicated for the treatment of severe pneumonia, complicated urinary tract infections, complicated intra-abdominal infections, complicated skin and soft tissue infections, or bacteraemia that arises from any of these infections. The UK National Institute for Health and Care Excellence (NICE) recommends piperacillin-tazobactam as initial empiric treatment for patients with suspected neutropenic sepsis [2].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com