tafamidis   Click here for help

GtoPdb Ligand ID: 8378

Synonyms: FX-1006 | Vyndamax® | Vyndaqel®
Approved drug PDB Ligand
tafamidis is an approved drug (EMA and UK (2011), FDA (2019))
Compound class: Synthetic organic
Comment: Tafamidis binds potently and selectively to transthyretin (TTR), stabilising protein tetramers, thereby inhibiting the formation of amyloid fibrils [2]. The trade name for this drug is Vyndaqel which contains tafamidis meglumine (PubChem CID 24970412). The Vyndamax brand contains tafamidis parent molecule.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 63.33
Molecular weight 306.98
XLogP 4.02
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1cc(Cl)cc(c1)c1nc2c(o1)cc(cc2)C(=O)O
Isomeric SMILES Clc1cc(Cl)cc(c1)c1nc2c(o1)cc(cc2)C(=O)O
InChI InChI=1S/C14H7Cl2NO3/c15-9-3-8(4-10(16)6-9)13-17-11-2-1-7(14(18)19)5-12(11)20-13/h1-6H,(H,18,19)
InChI Key TXEIIPDJKFWEEC-UHFFFAOYSA-N
Bioactivity Comments
Tafamidis binds within the thyroxine-binding sites of the TTR complex to stabilise the tetrameric structure [2]. It is able to stabilise wild-type and mutated TTR structures [5]. Information from X-ray crystal structures indicates that tafamidis stabilises the interaction between the two identical homodimers which form the tetrameric TTR complex. The dimer-dimer interaction is a relatively weak association and is the first to fail in tetramer dissociation [3].
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
transthyretin Hs Inhibitor Inhibition 8.7 pKd - 2
pKd 8.7 (Kd 2x10-9 M) [2]
Ligand mentioned in the following text fields