fexofenadine   

GtoPdb Ligand ID: 4819

Synonyms: Allegra® | fexofenadine HCl
fexofenadine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Fexofenadine is a metabolite of terfenadine. Fexofenadine is an antihistamine (histamine H1 receptor antagonist), non-sedating antiallergic agent. The approved drug is a racemic mixture of two enatiomers (CID 9870655) and (CID 6603853). The structure shown here does not specify stereochemistry and represents the mixture.

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure

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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Click here for structure editor
Physico-chemical Properties

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 5
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 81
Molecular weight 501.29
XLogP 5.64
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey

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 OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C
Isomeric SMILES OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C
InChI InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
InChI Key RWTNPBWLLIMQHL-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
IUPAC Name
2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
International Nonproprietary Names
INN number INN
7469 fexofenadine
Synonyms
Allegra® | fexofenadine HCl
Database Links
CAS Registry No. 83799-24-0 (source: Scifinder)
ChEMBL Ligand CHEMBL914
DrugBank Ligand DB00950
DrugCentral Ligand 1170
GtoPdb PubChem SID 178101521
PubChem CID 3348
Search Google for chemical match using the InChIKey RWTNPBWLLIMQHL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RWTNPBWLLIMQHL
Search PubMed clinical trials fexofenadine
Search PubMed titles fexofenadine
Search PubMed titles/abstracts fexofenadine
Search UniChem for chemical match using the InChIKey RWTNPBWLLIMQHL-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone RWTNPBWLLIMQHL
Wikipedia Fexofenadine