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
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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)
1. Ando Y, Suhr OB. (1998)
Autonomic dysfunction in familial amyloidotic polyneuropathy (FAP).
Amyloid, 5 (4): 288-300. [PMID:10036588]
2. Bulawa CE, Connelly S, Devit M, Wang L, Weigel C, Fleming JA, Packman J, Powers ET, Wiseman RL, Foss TR et al.. (2012)
Tafamidis, a potent and selective transthyretin kinetic stabilizer that inhibits the amyloid cascade.
Proc Natl Acad Sci USA, 109 (24): 9629-34. [PMID:22645360]
3. Foss TR, Wiseman RL, Kelly JW. (2005)
The pathway by which the tetrameric protein transthyretin dissociates.
Biochemistry, 44 (47): 15525-33. [PMID:16300401]
4. Griffin JM, Maurer MS. (2021)
Transthyretin cardiac amyloidosis: A treatable form of heart failure with a preserved ejection fraction.
Trends Cardiovasc Med, 31 (1): 59-66. [PMID:31889610]
5. Liu YT, Yen YJ, Ricardo F, Chang Y, Wu PH, Huang SJ, Lin KP, Yu TY. (2019)
Biophysical characterization and modulation of Transthyretin Ala97Ser.
Ann Clin Transl Neurol, 6 (10): 1961-1970. [PMID:31502419]
6. Park J, Egolum U, Parker S, Andrews E, Ombengi D, Ling H. (2020)
Tafamidis: A First-in-Class Transthyretin Stabilizer for Transthyretin Amyloid Cardiomyopathy.
Ann Pharmacother, 54 (5): 470-477. [PMID:31735059]
7. Westermark P, Sletten K, Johansson B, Cornwell 3rd GG. (1990)
Fibril in senile systemic amyloidosis is derived from normal transthyretin.
Proc Natl Acad Sci USA, 87 (7): 2843-5. [PMID:2320592]