tiludronic acid   

GtoPdb Ligand ID: 7604

Synonyms: CIPsMBP | Skelid® | SR-41319 | tiludronate
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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2D Structure
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Physico-chemical Properties
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
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
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
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].