pipemidic acid   Click here for help

GtoPdb Ligand ID: 12774

Synonyms: Pipram®
Approved drug
pipemidic acid is an approved drug
Compound class: Synthetic organic
Comment: Pipemidic acid is from a series of derivatives of piromidic acid, with enhanced antibacterial activity against Gram-negative bacteria, including against Pseudomonas aeruginosa and some Gram-positive spp. [2]. It is a pyridopyrimidine, structurally related to and classed with the quinolone antibacterials.
2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 97.6
Molecular weight 303.32
XLogP 0.02
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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.

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Canonical SMILES CCN1C=C(C(=O)C2=C1N=C(N=C2)N3CCNCC3)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=CN=C(N=C21)N3CCNCC3)C(=O)O
InChI InChI=1S/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22)
InChI Key JOHZPMXAZQZXHR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Withdrawn drug? Yes
IUPAC Name Click here for help
8-ethyl-5-oxo-2-piperazin-1-ylpyrido[6,5-d]pyrimidine-6-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3694 pipemidic acid
Synonyms Click here for help
Pipram®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Pipemidic acid
Other databases
CAS Registry No. 51940-44-4 (source: Scifinder)
ChEBI CHEBI:75250
ChEMBL Ligand CHEMBL30116
DrugBank Ligand DB13823
DrugCentral Ligand 2184
GtoPdb PubChem SID 483123322
PubChem CID 4831
Search Google for chemical match using the InChIKey JOHZPMXAZQZXHR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JOHZPMXAZQZXHR
Search PubMed clinical trials pipemidic acid
Search PubMed titles pipemidic acid
Search PubMed titles/abstracts pipemidic acid
UniChem Compound Search for chemical match using the InChIKey JOHZPMXAZQZXHR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JOHZPMXAZQZXHR-UHFFFAOYSA-N