tiludronic acid   Click here for help

GtoPdb Ligand ID: 7604

Synonyms: CIPsMBP | Skelid® | SR-41319 | tiludronate
Approved drug
tiludronic acid is an approved drug
Compound class: Synthetic organic
Comment: Tiludronic acid belongs to the same non-nitrogenous bisphosphonate drug family as etidronic acid and clodronic acid (PubChem CID 25419). Marketed formulations contain tiludronate disodium (PubChem CID 60936).
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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

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View more information in the IUPHAR Pharmacology Education Project: tiludronic acid

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 6
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 159.98
Molecular weight 317.93
XLogP -0.57
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 Clc1ccc(cc1)SC(P(=O)(O)O)P(=O)(O)O
Isomeric SMILES Clc1ccc(cc1)SC(P(=O)(O)O)P(=O)(O)O
InChI InChI=1S/C7H9ClO6P2S/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14/h1-4,7H,(H2,9,10,11)(H2,12,13,14)
InChI Key DKJJVAGXPKPDRL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Tiludronic acid is a bisphosphonate used to treat Paget's disease of bone, a disease caused by abnormal bone turnover, including excessive resorption and subsequent disorganised bone remodelling. There is no information regarding approval of this drug on either the US FDA or EMA websites. Individual national approval agencies may have granted marketing authorisation for this drug. In some countries only veterinary use is authorised.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Bisphosphonates bind to hydroxyapatite in calcified bone matrix and inhibit the activity of enzymes that utilize pyrophosphate. Non-nitrogenous bisphosphonates such as tiludronic acid are metabolised in osteoclasts to compounds that form non-functional ATP molecules. This non-functional ATP then competes with active ATP in energy metabolism within the cell. The effect is reduced energy metabolism which drives the osteoclasts into apoptotic cell death. The net drug-induced effect is inhibition of osteoclast-driven bone resorption [1].