tadalafil   Click here for help

GtoPdb Ligand ID: 7299

Synonyms: Adcirca® | Cialis® | IC-351 | IC351
Approved drug PDB Ligand
tadalafil is an approved drug (EMA (2002), FDA (2003))
Compound class: Synthetic organic
Comment: Tadafil is a phosphodiesterase type 5 (PDE5) inhibitor.
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tadalafil

tadalafil 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 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 74.87
Molecular weight 389.14
XLogP 1.75
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
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 O=C1N(C)CC(=O)N2C1Cc1c(C2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
Isomeric SMILES O=C1N(C)CC(=O)N2[C@@H]1Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
InChI InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
InChI Key WOXKDUGGOYFFRN-IIBYNOLFSA-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
Used to treat erectile dysfunction (ED), benign prostatic hyperplasia (BPH) and pulmonary arterial hypertension. The drug used to treat ED and BPH is approved as Cialis, and the drug approved for pulmonary arterial hypertension is Adcirca. Approvals for different indications have separate approval dates.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tadalafil is a selective phosphodiesterase type 5 (PDE5) inhibitor. Such inhibitors block the degradative action of PDE5 on cGMP in the smooth muscle cells lining the blood vessels supplying the corpus cavernosum of the penis. This action dilates these blood vessels allowing blood ingress and leads to functional erection. Vasoconstriction in the pulmonary vascular lumen causes PAH and tadalafil can also effect vasodilation in these vessels, thus reducing pulmonary arterial pressure. Due to its extended elimination half-life compared to other PDE5 inhibitors [1], this drug is useful for once-a-day dosing for patients with pulmonary arterial hypertension.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)