YM-543 free base

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MedKoo CAT#: 529918

CAS#: 655237-16-4 (free base)

Description: YM-543, also known as ASP-543, is a selective SGLT2 inhibitor. Sodium-glucose cotransporter 2 (SGLT2) is a specifically expressed transporter in the kidney that plays an important role in renal glucose reabsorption, and its inhibition may present a novel therapeutic strategy for treating diabetes. YM543 potently and selectively inhibited mouse and human SGLT2 activities at nanomolar ranges. In vivo single oral administration of YM543 dose-dependently and significantly reduced blood glucose levels and improved glucose tolerance with a concomitant increase in urinary glucose excretion in KK/Ay type 2 diabetic mice, effects that were sustained even after 12 h.

Chemical Structure

YM-543 free base
CAS# 655237-16-4 (free base)

Theoretical Analysis

MedKoo Cat#: 529918
Name: YM-543 free base
CAS#: 655237-16-4 (free base)
Chemical Formula: C23H24O6
Exact Mass: 396.1573
Molecular Weight: 396.439
Elemental Analysis: C, 69.68; H, 6.10; O, 24.21

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 918802-70-7 (choline)   918802-69-4 (anion)   655237-16-4 (free base)   1610007-47-0 (choline)    

Synonym: ASP-543; ASP 543; ASP543; YM 543, YM-543, YM543

IUPAC/Chemical Name: (2S,3R,4R,5S,6R)-2-(5-(azulen-2-ylmethyl)-2-hydroxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol


InChi Code: InChI=1S/C23H24O6/c24-12-19-20(26)21(27)22(28)23(29-19)17-11-13(6-7-18(17)25)8-14-9-15-4-2-1-3-5-16(15)10-14/h1-7,9-11,19-28H,8,12H2/t19-,20-,21+,22-,23+/m1/s1

SMILES Code: OC1=CC=C(CC2=CC3=CC=CC=CC3=C2)C=C1[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4

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: >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 396.439 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: Yokono M, Tahara A, Kurosaki E, Yamajuku D, Kihara R, Imamura M, Tomiyama H, Kobayashi Y, Noda A, Shibasaki M. Pharmacological Characterization of YM543, a Newly Synthesized, Orally Active SGLT2 Selective Inhibitor. Endocr Res. 2013 Feb 1. [Epub ahead of print] PubMed PMID: 23374077.

2: Ikegai K, Imamura M, Suzuki T, Nakanishi K, Murakami T, Kurosaki E, Noda A, Kobayashi Y, Yokota M, Koide T, Kosakai K, Ohkura Y, Takeuchi M, Tomiyama H, Ohta M. Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: discovery of YM543. Bioorg Med Chem. 2013 Jul 1;21(13):3934-48. doi: 10.1016/j.bmc.2013.03.067. PubMed PMID: 23651509. 3: Brüser A, Kirchberger J, Schöneberg T. Altered allosteric regulation of muscle 6-phosphofructokinase causes Tarui disease. Biochem Biophys Res Commun. 2012 Oct 12;427(1):133-7. doi: 10.1016/j.bbrc.2012.09.024. Erratum in: Biochem Biophys Res Commun. 2013 Feb 8;431(2):367. PubMed PMID: 22995305.

4: Someya A, Sata M, Takeda K, Pacheco-Rodriguez G, Ferrans VJ, Moss J, Vaughan M. ARF-GEP(100), a guanine nucleotide-exchange protein for ADP-ribosylation factor 6. Proc Natl Acad Sci U S A. 2001 Feb 27;98(5):2413-8. PubMed PMID: 11226253; PubMed Central PMCID: PMC30152.

5: Matsumura H, Terada M, Shirakata S, Inoue T, Yoshinaga T, Izui K, Kai Y. Plausible phosphoenolpyruvate binding site revealed by 2.6 A structure of Mn2+-bound phosphoenolpyruvate carboxylase from Escherichia coli. FEBS Lett. 1999 Sep 17;458(2):93-6. PubMed PMID: 10481043.