Tafamidis

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319842

CAS#: 594839-88-0

Description: 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. In patients with FAP, this protein dissociates in a process that is rate limiting for aggregation including amyloid fibril formation, causing failure of the autonomic nervous system and/or the peripheral nervous system (neurodegeneration) initially and later failure of the heart.


Price and Availability

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Tafamidis is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319842
Name: Tafamidis
CAS#: 594839-88-0
Chemical Formula: C14H7Cl2NO3
Exact Mass: 306.9803
Molecular Weight: 308.114
Elemental Analysis: C, 54.58; H, 2.29; Cl, 23.01; N, 4.55; O, 15.58


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


Technical Data

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).

Harmonized System Code:
293490


References

1: Waddington Cruz M, Benson MD. A Review of Tafamidis for the Treatment of Transthyretin-Related Amyloidosis. Neurol Ther. 2015 Dec;4(2):61-79. doi: 10.1007/s40120-015-0031-3. Epub 2015 Aug 15. PubMed PMID: 26662359; PubMed Central PMCID: PMC4685869.

2: Cho Y, Baranczak A, Helmke S, Teruya S, Horn EM, Maurer MS, Kelly JW. Personalized medicine approach for optimizing the dose of tafamidis to potentially ameliorate wild-type transthyretin amyloidosis (cardiomyopathy). Amyloid. 2015;22(3):175-80. doi: 10.3109/13506129.2015.1063485. Epub 2015 Jul 25. PubMed PMID: 26193961; PubMed Central PMCID: PMC4549186.

3: Kon T, Misumi Y, Nishijima H, Honda M, Suzuki C, Baba M, Inomata Y, Obayashi K, Ando Y, Tomiyama M. Effects of liver transplantation and tafamidis in hereditary transthyretin amyloidosis caused by transthyretin Leu55Pro mutation: a case report. Amyloid. 2015;22(3):203-4. doi: 10.3109/13506129.2015.1031373. Epub 2015 Jul 2. PubMed PMID: 26123280.

4: Suhr OB, Conceição IM, Karayal ON, Mandel FS, Huertas PE, Ericzon BG. Post hoc analysis of nutritional status in patients with transthyretin familial amyloid polyneuropathy: impact of tafamidis. Neurol Ther. 2014 Dec 11;3(2):101-12. doi: 10.1007/s40120-014-0023-8. eCollection 2014 Dec. PubMed PMID: 26000226; PubMed Central PMCID: PMC4386428.

5: Maurer MS, Grogan DR, Judge DP, Mundayat R, Packman J, Lombardo I, Quyyumi AA, Aarts J, Falk RH. Tafamidis in transthyretin amyloid cardiomyopathy: effects on transthyretin stabilization and clinical outcomes. Circ Heart Fail. 2015 May;8(3):519-26. doi: 10.1161/CIRCHEARTFAILURE.113.000890. Epub 2015 Apr 14. PubMed PMID: 25872787.

6: Damy T, Judge DP, Kristen AV, Berthet K, Li H, Aarts J. Cardiac findings and events observed in an open-label clinical trial of tafamidis in patients with non-Val30Met and non-Val122Ile hereditary transthyretin amyloidosis. J Cardiovasc Transl Res. 2015 Mar;8(2):117-27. doi: 10.1007/s12265-015-9613-9. Epub 2015 Mar 6. PubMed PMID: 25743445; PubMed Central PMCID: PMC4382536.

7: Klamerus KJ, Watsky E, Moller R, Wang R, Riley S. The effect of tafamidis on the QTc interval in healthy subjects. Br J Clin Pharmacol. 2015 Jun;79(6):918-25. doi: 10.1111/bcp.12561. PubMed PMID: 25546001; PubMed Central PMCID: PMC4456124.

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: Sekijima Y. [Newly developed drug therapies for familial amyloid polyneuropathy: diflunisal and tafamidis]. Brain Nerve. 2014 Jul;66(7):773-81. Japanese. PubMed PMID: 24998822.

10: Merlini G, Planté-Bordeneuve V, Judge DP, Schmidt H, Obici L, Perlini S, Packman J, Tripp T, Grogan DR. Effects of tafamidis on transthyretin stabilization and clinical outcomes in patients with non-Val30Met transthyretin amyloidosis. J Cardiovasc Transl Res. 2013 Dec;6(6):1011-20. doi: 10.1007/s12265-013-9512-x. Epub 2013 Oct 8. PubMed PMID: 24101373; PubMed Central PMCID: PMC3838581.

11: Nencetti S, Rossello A, Orlandini E. Tafamidis (Vyndaqel): a light for FAP patients. ChemMedChem. 2013 Oct;8(10):1617-9. doi: 10.1002/cmdc.201300245. Epub 2013 Sep 2. PubMed PMID: 24000164.

12: Coelho T, Maia LF, da Silva AM, Cruz MW, Planté-Bordeneuve V, Suhr OB, Conceiçao I, Schmidt HH, Trigo P, Kelly JW, Labaudinière R, Chan J, Packman J, Grogan DR. Long-term effects of tafamidis for the treatment of transthyretin familial amyloid polyneuropathy. J Neurol. 2013 Nov;260(11):2802-14. doi: 10.1007/s00415-013-7051-7. Epub 2013 Aug 22. PubMed PMID: 23974642; PubMed Central PMCID: PMC3825212.

13: Lozeron P, Théaudin M, Mincheva Z, Ducot B, Lacroix C, Adams D; French Network for FAP (CORNAMYL). Effect on disability and safety of Tafamidis in late onset of Met30 transthyretin familial amyloid polyneuropathy. Eur J Neurol. 2013 Dec;20(12):1539-45. doi: 10.1111/ene.12225. Epub 2013 Jul 9. PubMed PMID: 23834402.

14: Merkies IS. Tafamidis for transthyretin familial amyloid polyneuropathy: a randomized, controlled trial. Neurology. 2013 Apr 9;80(15):1444-5. doi: 10.1212/01.wnl.0000429338.33391.87. PubMed PMID: 23569001.

15: de Carvalho M. Is it better than it seems or just good enough? The tafamidis saga. Muscle Nerve. 2012 Dec;46(6):839-40. doi: 10.1002/mus.23665. Epub 2012 Oct 5. PubMed PMID: 23042137.

16: Coelho T, Maia LF, Martins da Silva A, Waddington Cruz M, Planté-Bordeneuve V, Lozeron P, Suhr OB, Campistol JM, Conceição IM, Schmidt HH, Trigo P, Kelly JW, Labaudinière R, Chan J, Packman J, Wilson A, Grogan DR. Tafamidis for transthyretin familial amyloid polyneuropathy: a randomized, controlled trial. Neurology. 2012 Aug 21;79(8):785-92. doi: 10.1212/WNL.0b013e3182661eb1. Epub 2012 Jul 25. PubMed PMID: 22843282; PubMed Central PMCID: PMC4098875.

17: 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.

18: Bulawa CE, Connelly S, Devit M, Wang L, Weigel C, Fleming JA, Packman J, Powers ET, Wiseman RL, Foss TR, Wilson IA, Kelly JW, Labaudinière R. Tafamidis, a potent and selective transthyretin kinetic stabilizer that inhibits the amyloid cascade. Proc Natl Acad Sci U S A. 2012 Jun 12;109(24):9629-34. doi: 10.1073/pnas.1121005109. Epub 2012 May 29. PubMed PMID: 22645360; PubMed Central PMCID: PMC3386102.

19: Said G, Grippon S, Kirkpatrick P. Tafamidis. Nat Rev Drug Discov. 2012 Mar 1;11(3):185-6. doi: 10.1038/nrd3675. PubMed PMID: 22378262.