Fasiglifam
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MedKoo CAT#: 504110

CAS#: 1000413-72-8

Description: Fasiglifam, also known as TAK-875, is a potent, selective, and orally bioavailable GPR40 agonist, with a pharmacokinetic profile enabling long-acting drug efficacy. TAK-875 showed potent plasma glucose-lowering action and insulinotropic action during an oral glucose tolerance test in female Wistar fatty rats with impaired glucose tolerance. TAK-875 is currently in clinical trials for the treatment of type 2 diabetes mellitus.


Chemical Structure

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Fasiglifam
CAS# 1000413-72-8

Theoretical Analysis

MedKoo Cat#: 504110
Name: Fasiglifam
CAS#: 1000413-72-8
Chemical Formula: C29H32O7S
Exact Mass: 524.18687
Molecular Weight: 524.63
Elemental Analysis: C, 66.39; H, 6.15; O, 21.35; S, 6.11

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Same day
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 750.0 Same day
500.0mg USD 1750.0 Same day
1.0g USD 2750.0 Same day
2.0g USD 4250.0 2 weeks
5.0g USD 7450.0 2 weeks
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Synonym: TAK875; TAK-875; TAK 875; Fasiglifam.

IUPAC/Chemical Name: (S)-2-(6-((2',6'-dimethyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

InChi Key: BZCALJIHZVNMGJ-HSZRJFAPSA-N

InChi Code: InChI=1S/C29H32O7S/c1-19-12-25(34-10-5-11-37(3,32)33)13-20(2)29(19)22-7-4-6-21(14-22)17-35-24-8-9-26-23(15-28(30)31)18-36-27(26)16-24/h4,6-9,12-14,16,23H,5,10-11,15,17-18H2,1-3H3,(H,30,31)/t23-/m1/s1

SMILES Code: O=C(O)C[C@@H]1COC2=CC(OCC3=CC(C4=C(C)C=C(OCCCS(=O)(C)=O)C=C4C)=CC=C3)=CC=C12

Appearance: white to off-white 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

Preparing Stock Solutions

The following data is based on the product molecular weight 524.63 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

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1: Yabuki C, Komatsu H, Tsujihata Y, Maeda R, Ito R, Matsuda-Nagasumi K, Sakuma K, Miyawaki K, Kikuchi N, Takeuchi K, Habata Y, Mori M. A novel antidiabetic drug, fasiglifam/TAK-875, acts as an ago-allosteric modulator of FFAR1. PLoS One. 2013 Oct 10;8(10):e76280. doi: 10.1371/journal.pone.0076280. eCollection 2013. PubMed PMID: 24130766; PubMed Central PMCID: PMC3794927.

2: Naik H, Lu J, Cao C, Pfister M, Vakilynejad M, Leifke E. Pharmacometric Approaches to Guide Dose Selection of the Novel GPR40 Agonist TAK-875 in Subjects With Type 2 Diabetes Mellitus. CPT Pharmacometrics Syst Pharmacol. 2013 Jan 9;2:e22. doi: 10.1038/psp.2012.23. PubMed PMID: 23887592; PubMed Central PMCID: PMC3600727.

3: Ito R, Tsujihata Y, Matsuda-Nagasumi K, Mori I, Negoro N, Takeuchi K. TAK-875, a GPR40/FFAR1 agonist, in combination with metformin prevents progression of diabetes and β-cell dysfunction in Zucker diabetic fatty rats. Br J Pharmacol. 2013 Oct;170(3):568-80. doi: 10.1111/bph.12297. PubMed PMID: 23848179; PubMed Central PMCID: PMC3791995.

4: Kaku K, Araki T, Yoshinaka R. Randomized, double-blind, dose-ranging study of TAK-875, a novel GPR40 agonist, in Japanese patients with inadequately controlled type 2 diabetes. Diabetes Care. 2013 Feb;36(2):245-50. doi: 10.2337/dc12-0872. Epub 2012 Oct 18. PubMed PMID: 23086138; PubMed Central PMCID: PMC3554318.

5: Leifke E, Naik H, Wu J, Viswanathan P, Demanno D, Kipnes M, Vakilynejad M. A multiple-ascending-dose study to evaluate safety, pharmacokinetics, and pharmacodynamics of a novel GPR40 agonist, TAK-875, in subjects with type 2 diabetes. Clin Pharmacol Ther. 2012 Jul;92(1):29-39. doi: 10.1038/clpt.2012.43. Epub 2012 Jun 6. PubMed PMID: 22669289.

6: Burant CF, Viswanathan P, Marcinak J, Cao C, Vakilynejad M, Xie B, Leifke E. TAK-875 versus placebo or glimepiride in type 2 diabetes mellitus: a phase 2, randomised, double-blind, placebo-controlled trial. Lancet. 2012 Apr 14;379(9824):1403-11. doi: 10.1016/S0140-6736(11)61879-5. Epub 2012 Feb 27. PubMed PMID: 22374408.

7: Yashiro H, Tsujihata Y, Takeuchi K, Hazama M, Johnson PR, Rorsman P. The effects of TAK-875, a selective G protein-coupled receptor 40/free fatty acid 1 agonist, on insulin and glucagon secretion in isolated rat and human islets. J Pharmacol Exp Ther. 2012 Feb;340(2):483-9. doi: 10.1124/jpet.111.187708. Epub 2011 Nov 21. PubMed PMID: 22106100.

8: Araki T, Hirayama M, Hiroi S, Kaku K. GPR40-induced insulin secretion by the novel agonist TAK-875: first clinical findings in patients with type 2 diabetes. Diabetes Obes Metab. 2012 Mar;14(3):271-8. doi: 10.1111/j.1463-1326.2011.01525.x. Epub 2011 Dec 22. PubMed PMID: 22051148.

9: Tsujihata Y, Ito R, Suzuki M, Harada A, Negoro N, Yasuma T, Momose Y, Takeuchi K. TAK-875, an orally available G protein-coupled receptor 40/free fatty acid receptor 1 agonist, enhances glucose-dependent insulin secretion and improves both postprandial and fasting hyperglycemia in type 2 diabetic rats. J Pharmacol Exp Ther. 2011 Oct;339(1):228-37. doi: 10.1124/jpet.111.183772. Epub 2011 Jul 13. PubMed PMID: 21752941.

10: Naik H, Vakilynejad M, Wu J, Viswanathan P, Dote N, Higuchi T, Leifke E. Safety, tolerability, pharmacokinetics, and pharmacodynamic properties of the GPR40 agonist TAK-875: results from a double-blind, placebo-controlled single oral dose rising study in healthy volunteers. J Clin Pharmacol. 2012 Jul;52(7):1007-16. doi: 10.1177/0091270011409230. Epub 2011 May 24. PubMed PMID: 21610201.

11: Molecule of the Month. TAK-875. Drug News Perspect. 2010 Dec;23(10):667. doi: 10.1358/dnp.2010.23.10.1560199. PubMed PMID: 21180652.



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