urapidil   Click here for help

GtoPdb Ligand ID: 13357

Synonyms: B 66256 | B-66256 | B66256 | Ebrantil®
Approved drug
urapidil is an approved drug
Compound class: Synthetic organic
Comment: Urapidil is a piperazine compound. It has activity as an α1-adrenoceptor antagonist and as a 5-HT1A receptor agonist [1,3].

urapidil is commercially available from our sponsors

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 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.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 68.36
Molecular weight 387.48
XLogP 1.05
No. Lipinski's rules broken 0

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
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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.

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/)

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Canonical SMILES CN1C(=CC(=O)N(C)C1=O)NCCCN2CCN(CC2)C3=C(C=CC=C3)OC
Isomeric SMILES CN1C(=CC(=O)N(C1=O)C)NCCCN2CCN(CC2)C3=CC=CC=C3OC
InChI InChI=1S/C20H29N5O3/c1-22-18(15-19(26)23(2)20(22)27)21-9-6-10-24-11-13-25(14-12-24)16-7-4-5-8-17(16)28-3/h4-5,7-8,15,21H,6,9-14H2,1-3H3
InChI Key ICMGLRUYEQNHPF-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
3169 urapidil
Synonyms Click here for help
B 66256 | B-66256 | B66256 | Ebrantil®
Database Links Click here for help
BindingDB Ligand 50237617
CAS Registry No. 34661-75-1 (source: PubChem)
ChEMBL Ligand CHEMBL279229
DrugBank Ligand DB12661
GtoPdb PubChem SID 496703327
PubChem CID 5639
Search Google for chemical match using the InChIKey ICMGLRUYEQNHPF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ICMGLRUYEQNHPF
Search PubMed clinical trials urapidil
Search PubMed titles urapidil
Search PubMed titles/abstracts urapidil
UniChem Compound Search for chemical match using the InChIKey ICMGLRUYEQNHPF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ICMGLRUYEQNHPF-UHFFFAOYSA-N

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MedChemExpress
Urapidil (links to external site)
Cat. No. HY-B0716