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MedKoo Cat#: 555364 | Name: Firuglipel

Description:

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

Firuglipel, also known as DS-8500a, is an orally available G protein-coupled receptor 119 agonist. DS-8500a upregulates glucagon-like peptide-1 and enhances glucose-dependent insulin secretion and improves glucose homeostasis in type 2 diabetic rats.

Chemical Structure

Firuglipel
Firuglipel
CAS#1371591-51-3

Theoretical Analysis

MedKoo Cat#: 555364

Name: Firuglipel

CAS#: 1371591-51-3

Chemical Formula: C25H26FN3O5

Exact Mass: 467.1856

Molecular Weight: 467.50

Elemental Analysis: C, 64.23; H, 5.61; F, 4.06; N, 8.99; O, 17.11

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
DS-8500a; DS 8500a; DS8500a; DS-8500; DS 8500; DS8500; Firuglipel
IUPAC/Chemical Name
4-[5-[(1S)-1-[4-(Cyclopropanecarbonyl)phenoxy]propyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-N-[(2S)-1-hydroxypropan-2-yl]benzamide
InChi Key
LRXRIKVDAVVQCP-QKKBWIMNSA-N
InChi Code
InChI=1S/C25H26FN3O5/c1-3-21(33-18-9-6-16(7-10-18)22(31)15-4-5-15)25-28-23(29-34-25)17-8-11-19(20(26)12-17)24(32)27-14(2)13-30/h6-12,14-15,21,30H,3-5,13H2,1-2H3,(H,27,32)/t14-,21-/m0/s1
SMILES Code
O=C(N[C@@H](C)CO)C1=CC=C(C2=NOC([C@@H](OC3=CC=C(C(C4CC4)=O)C=C3)CC)=N2)C=C1F
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
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 467.50 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
1: Matsumoto K, Yoshitomi T, Ishimoto Y, Tanaka N, Takahashi K, Watanabe A, Chiba K. DS-8500a, an Orally Available G Protein-Coupled Receptor 119 Agonist, Upregulates Glucagon-Like Peptide-1 and Enhances Glucose-Dependent Insulin Secretion and Improves Glucose Homeostasis in Type 2 Diabetic Rats. J Pharmacol Exp Ther. 2018 Dec;367(3):509-517. doi: 10.1124/jpet.118.250019. Epub 2018 Sep 14. PubMed PMID: 30217957. 2: Matsumoto K, Yoshitomi T, Shimada T. [The role of pharmacology to produce firuglipel (DS-8500a), an orally available GPR119 agonist for type 2 diabetes mellitus]. Nihon Yakurigaku Zasshi. 2018;152(3):119-124. doi: 10.1254/fpj.152.119. Japanese. PubMed PMID: 30185729. 3: Makino C, Watanabe A, Deguchi T, Shiozawa H, Schreck I, Rozehnal V, Ishizuka T, Watanabe N, Ando O, Murayama N, Yamazaki H. In vivo multiple metabolic pathways for a novel G protein-coupled receptor 119 agonist DS-8500a in rats: involvement of the 1,2,4-oxadiazole ring-opening reductive reaction in livers under anaerobic conditions. Xenobiotica. 2018 Sep 28:1-9. doi: 10.1080/00498254.2018.1514545. [Epub ahead of print] PubMed PMID: 30124356. 4: Kato M, Ishizuka H, Taguchi T, Shiosakai K, Kamiyama E, Sata M, Yoshida T. Pharmacokinetics and Safety of DS-8500a, an Antidiabetic Drug, in Japanese Subjects with Hepatic or Renal Impairment: A Single-Center, Open-Label, Single-Dose Study. Adv Ther. 2018 Aug;35(8):1239-1250. doi: 10.1007/s12325-018-0739-4. Epub 2018 Jul 2. PubMed PMID: 29968010. 5: Watada H, Shiramoto M, Irie S, Terauchi Y, Yamada Y, Shiosakai K, Myobatake Y, Taguchi T. G protein-coupled receptor 119 agonist DS-8500a effects on pancreatic β-cells in Japanese type 2 diabetes mellitus patients. J Diabetes Investig. 2018 Apr 6. doi: 10.1111/jdi.12849. [Epub ahead of print] PubMed PMID: 29624887. 6: Terauchi Y, Yamada Y, Watada H, Nakatsuka Y, Shiosakai K, Washio T, Taguchi T. Efficacy and safety of the G protein-coupled receptor 119 agonist DS-8500a in Japanese type 2 diabetes mellitus patients with inadequate glycemic control on sitagliptin: A phase 2 randomized placebo-controlled study. J Diabetes Investig. 2018 Nov;9(6):1333-1341. doi: 10.1111/jdi.12846. Epub 2018 May 24. PubMed PMID: 29607623; PubMed Central PMCID: PMC6215943. 7: Kato M, Furuie H, Kamiyama E, Shiosakai K, Yoshihara K, Taguchi T. Safety and Pharmacokinetics of DS-8500a, a Novel GPR119 Agonist, After Multiple Oral Doses in Healthy Japanese Males. Clin Drug Investig. 2018 Jun;38(6):519-525. doi: 10.1007/s40261-018-0633-5. PubMed PMID: 29582248. 8: Yamada Y, Terauchi Y, Watada H, Nakatsuka Y, Shiosakai K, Washio T, Taguchi T. Efficacy and Safety of GPR119 Agonist DS-8500a in Japanese Patients with Type 2 Diabetes: a Randomized, Double-Blind, Placebo-Controlled, 12-Week Study. Adv Ther. 2018 Mar;35(3):367-381. doi: 10.1007/s12325-018-0668-2. Epub 2018 Feb 27. PubMed PMID: 29488152; PubMed Central PMCID: PMC5859088. 9: Inagaki N, Chou HS, Tsukiyama S, Washio T, Shiosakai K, Nakatsuka Y, Taguchi T. Glucose-lowering effects and safety of DS-8500a, a G protein-coupled receptor 119 agonist, in Japanese patients with type 2 diabetes: results of a randomized, double-blind, placebo-controlled, parallel-group, multicenter, phase II study. BMJ Open Diabetes Res Care. 2017 Sep 29;5(1):e000424. doi: 10.1136/bmjdrc-2017-000424. eCollection 2017. PubMed PMID: 29071087; PubMed Central PMCID: PMC5640040.

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