Tafamidis
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MedKoo CAT#: 319842

CAS#: 594839-88-0 (free acid)

Description: Tafamidis, Tafamidis, also known as Fx-1006 or PF-06291826, is a drug for the amelioration of transthyretin-related hereditary amyloidosis (also familial amyloid polyneuropathy, or FAP), a rare but deadly neurodegenerative disease. The drug was approved by the European Medicines Agency in November 2011 and by the Japanese Pharmaceuticals and Medical Devices Agency in September 2013. Tafamidis functions by kinetic stabilization of the correctly folded tetrameric form of the transthyretin (TTR) protein.


Chemical Structure

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Tafamidis
CAS# 594839-88-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 319842
Name: Tafamidis
CAS#: 594839-88-0 (free acid)
Chemical Formula: C14H7Cl2NO3
Exact Mass: 306.98
Molecular Weight: 308.114
Elemental Analysis: C, 54.58; H, 2.29; Cl, 23.01; N, 4.55; O, 15.58

Price and Availability

Size Price Availability Quantity
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1350 Ready to ship
1g USD 2350 Ready to ship
25mg USD 150 Ready to ship
2g USD 3950 Ready to ship
50mg USD 250 Ready to ship
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Related CAS #: 594839-88-0 (free acid), 951395-08-7 (meglumine),

Synonym: Fx-1006, Fx1006, Fx 1006, Fx-1006A; PF-06291826; PF06291826; PF 06291826; Tafamidis; Vyndaqel

IUPAC/Chemical Name: 2-(3,5-dichlorophenyl)benzo[d]oxazole-6-carboxylic acid

InChi Key: TXEIIPDJKFWEEC-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=CC=C2N=C(C3=CC(Cl)=CC(Cl)=C3)OC2=C1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:
Biological target: Tafamidis is a kinetic stabilizer of transthyretin (TTR) that prevents amyloidogenesis by wild-type and mutant TTRs.
In vitro activity: At a ligand:TTR tetramer molar ratio of 0.5:1, mds84 tafamidis reduced fibril formation by 40%. At molar equivalence, inhibition increased at 60% with tafamidis. At twofold and greater molar excess of ligand, both monovalent ligands, tafamidis inhibited TTR fibrillogenesis by the same amount (~90%) as mds84. Reference: Sci Rep. 2017 Mar 15;7(1):182. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5428290/
In vivo activity: Tafamidis, a novel drug to treat transthyretin-related amyloidosis, was studied in rats after intravenous and oral administration at doses of 0.3-3 mg/kg. After intravenous injection, systemic clearance (CL), volumes of distribution at steady state (Vss) and half-life (T½) remained unaltered as a function of dose, with values in the ranges of 6.41-7.03 mL/h/kg, 270-354 mL/kg and 39.5-46.9 h, respectively. Following oral administration, absolute bioavailability was 99.7-104% and was independent of doses from 0.3 to 3 mg/kg. In the urine and faeces, 4.36% and 48.9% of tafamidis, respectively, were recovered. Tafamidis was distributed primarily in the liver and not in the brain, kidney, testis, heart, spleen, lung, gut, muscle, or adipose tissue. Further, tafamidis was very stable in rat liver microsomes, and its plasma protein binding was 99.9%. Reference: Xenobiotica. 2018 Aug;48(8):831-838. https://www.tandfonline.com/doi/full/10.1080/00498254.2017.1366575

Preparing Stock Solutions

The following data is based on the product molecular weight 308.114000000000000000000000000000 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Verona G, Mangione PP, Raimondi S, Giorgetti S, Faravelli G, Porcari R, Corazza A, Gillmore JD, Hawkins PN, Pepys MB, Taylor GW, Bellotti V. Inhibition of the mechano-enzymatic amyloidogenesis of transthyretin: role of ligand affinity, binding cooperativity and occupancy of the inner channel. Sci Rep. 2017 Mar 15;7(1):182. doi: 10.1038/s41598-017-00338-x. PMID: 28298647; PMCID: PMC5428290. 2. Lee KR, Jeong JW, Hyun HC, Jang E, Ahn S, Choi S, Joo SH, Kim S, Koo TS. Pharmacokinetics of tafamidis, a transthyretin amyloidosis drug, in rats. Xenobiotica. 2018 Aug;48(8):831-838. doi: 10.1080/00498254.2017.1366575. Epub 2017 Nov 16. PMID: 28803538.
In vitro protocol: 1. Verona G, Mangione PP, Raimondi S, Giorgetti S, Faravelli G, Porcari R, Corazza A, Gillmore JD, Hawkins PN, Pepys MB, Taylor GW, Bellotti V. Inhibition of the mechano-enzymatic amyloidogenesis of transthyretin: role of ligand affinity, binding cooperativity and occupancy of the inner channel. Sci Rep. 2017 Mar 15;7(1):182. doi: 10.1038/s41598-017-00338-x. PMID: 28298647; PMCID: PMC5428290.
In vivo protocol: 1. Lee KR, Jeong JW, Hyun HC, Jang E, Ahn S, Choi S, Joo SH, Kim S, Koo TS. Pharmacokinetics of tafamidis, a transthyretin amyloidosis drug, in rats. Xenobiotica. 2018 Aug;48(8):831-838. doi: 10.1080/00498254.2017.1366575. Epub 2017 Nov 16. PMID: 28803538.

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1: Cruz MW. Tafamidis for autonomic neuropathy in hereditary transthyretin (ATTR) amyloidosis: a review. Clin Auton Res. 2019 Sep;29(Suppl 1):19-24. doi: 10.1007/s10286-019-00625-9. Epub 2019 Aug 12. Review. PubMed PMID: 31407119; PubMed Central PMCID: PMC6763524. 2: Lamb YN, Deeks ED. Tafamidis: A Review in Transthyretin Amyloidosis with Polyneuropathy. Drugs. 2019 Jun;79(8):863-874. doi: 10.1007/s40265-019-01129-6. Review. PubMed PMID: 31098895. 3: Lorenzini M, Elliott PM. Tafamidis for the treatment of transthyretin amyloidosis. Future Cardiol. 2019 Mar;15(2):53-61. doi: 10.2217/fca-2018-0078. Epub 2019 Feb 15. Review. PubMed PMID: 30767672. 4: Planté-Bordeneuve V, Lin H, Gollob J, Agarwal S, Betts M, Fahrbach K, Chitnis M, Polydefkis M. An indirect treatment comparison of the efficacy of patisiran and tafamidis for the treatment of hereditary transthyretin-mediated amyloidosis with polyneuropathy. Expert Opin Pharmacother. 2019 Mar;20(4):473-481. doi: 10.1080/14656566.2018.1554648. Epub 2018 Dec 12. Review. PubMed PMID: 30489166. 5: Maurer MS, Elliott P, Merlini G, Shah SJ, Cruz MW, Flynn A, Gundapaneni B, Hahn C, Riley S, Schwartz J, Sultan MB, Rapezzi C; ATTR-ACT Study Investigators. Design and Rationale of the Phase 3 ATTR-ACT Clinical Trial (Tafamidis in Transthyretin Cardiomyopathy Clinical Trial). Circ Heart Fail. 2017 Jun;10(6). pii: e003815. doi: 10.1161/CIRCHEARTFAILURE.116.003815. Review. PubMed PMID: 28611125. 6: Institute for Quality and Efficiency in Health Care. Tafamidis Meglumine -- Benefit Assessment According to §35a Social Code Book V [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2012 Mar 13. Available from http://www.ncbi.nlm.nih.gov/books/NBK385651/ PubMed PMID: 27905733. 7: Coelho T, Merlini G, Bulawa CE, Fleming JA, Judge DP, Kelly JW, Maurer MS, Planté-Bordeneuve V, Labaudinière R, Mundayat R, Riley S, Lombardo I, Huertas P. Mechanism of Action and Clinical Application of Tafamidis in Hereditary Transthyretin Amyloidosis. Neurol Ther. 2016 Jun;5(1):1-25. doi: 10.1007/s40120-016-0040-x. Epub 2016 Feb 19. Review. PubMed PMID: 26894299; PubMed Central PMCID: PMC4919130. 8: Scott LJ. Tafamidis: a review of its use in familial amyloid polyneuropathy. Drugs. 2014 Aug;74(12):1371-8. doi: 10.1007/s40265-014-0260-2. Review. PubMed PMID: 25022953. 9: Buxbaum JN. Evaluation of tafamidis as first-line therapeutic agent for transthyretin familial amyloidotic polyneuropathy. Degener Neurol Neuromuscul Dis. 2012 Oct 19;2:165-173. doi: 10.2147/DNND.S24624. eCollection 2012. Review. PubMed PMID: 30890886; PubMed Central PMCID: PMC6065585. 10: de Lartigue J. Tafamidis for transthyretin amyloidosis. Drugs Today (Barc). 2012 May;48(5):331-7. doi: 10.1358/dot.2012.48.5.1808486. Review. PubMed PMID: 22645721.