MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 319791 | Name: Ipragliflozin
Featured New

Description:

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

Ipragliflozin, also known as ASP1941, is a potent and selective SGLT2 inhibitor for treatment of type 2 diabetes. Ipragliflozin treatment improved glycaemic control when added to metformin therapy and may be associated with weight loss and reductions in blood pressure compared to placebo. Ipragliflozin improves not only hyperglycemia but also diabetes/obesity-associated metabolic abnormalities in type 2 diabetic mice. It was approved for use in Japan in 2014.

Chemical Structure

Ipragliflozin
Ipragliflozin
CAS#761423-87-4

Theoretical Analysis

MedKoo Cat#: 319791

Name: Ipragliflozin

CAS#: 761423-87-4

Chemical Formula: C21H21FO5S

Exact Mass: 404.1094

Molecular Weight: 404.45

Elemental Analysis: C, 62.36; H, 5.23; F, 4.70; O, 19.78; S, 7.93

Price and Availability

Size Price Availability Quantity
100mg USD 150.00 Ready to ship
200mg USD 250.00 Ready to ship
500mg USD 500.00 Ready to ship
1g USD 800.00 Ready to ship
2g USD 1,350.00 Ready to ship
5g USD 2,650.00 Ready to ship
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
ASP1941; ASP-1941; ASP 1941; Ipragliflozin. Trade name: Suglat.
IUPAC/Chemical Name
(2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
InChi Key
AHFWIQIYAXSLBA-RQXATKFSSA-N
InChi Code
InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1
SMILES Code
O[C@H]1[C@H](C2=CC=C(F)C(CC3=CC4=CC=CC=C4S3)=C2)O[C@H](CO)[C@@H](O)[C@@H]1O
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
More Info
Biological target:
Ipragliflozin (ASP1941) is an orally active and selective SGLT2 inhibitor with IC50s of 7.38 and 1876 nM, 6.73 and 1166 nM, 5.64 and 1380 nM for human SGLT2 and SGLT1, rat SGLT2 and SGLT1, mouse SGLT2 and SGLT1, respectively.
In vitro activity:
Ipragliflozin concentration-dependently inhibits mouse, rat, and human SGLT2 activity at nanomolar concentrations. Furthermore, ipragliflozin does not potently inhibit human SGLT4 and SGLT5 isoforms (IC50>1,000 nM). In addition, ipragliflozin does not inhibit several glucose transporter (GLUT) isoforms, including GLUT1 and GLUT4, in mouse 3T3-L1, rat L6, human Caco-2, and HepG2 cells (IC50>1,000 nM). Ipragliflozin does not interact with various receptors, ion channels, and transporters such as adrenergic (α1, α2, and β), muscarinic (M1, M2, and non-selective), angiotensin(AT1 and AT2), calcium channel (L-type and N-type), potassium channel (KATP and SKCa), sodium channel (site 2), cholecystokinin (CCKA and CCKB), dopamine (D1, D2, and transporter), endothelin (ETA and ETB), gamma-aminobutyric acid (GABAA and GABAB), glutamate (AMPA, kainate, and NMDA), serotonin (5-HT1, 5HT2B, and transporter), histamine (H1, H2, and H3), and neurokinin (NK1, NK2, and NK3), exhibiting IC50 values >3,000 nM. Ipragliflozi is stable against mouse intestinal glucosidases. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36. https://dx.doi.org/10.1007/s00210-011-0713-z
In vivo activity:
As shown in Figure 2, single oral doses (0.01–10 mg/kg) of ipragliflozin (14h) induced urinary glucose excretion in a dose-dependent manner in both normal and in KK-Ay mice, a type 2 diabetes model. To assess antihyperglycemic effects, KK-Ay mice and streptozotocin-induced diabetic rats (STZ rats, a type 1 diabetes model) were used to evaluate the efficacy of 14h for lowering blood glucose levels. Figure 3 shows that single administrations of 14h (0.1, 0.3 and 1 mg/kg) dose-dependently reduces blood glucose level in both KK-Ay mice and STZ rats. Reference: Bioorg Med Chem. 2012 May 15;20(10):3263-79. https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(12)00241-6
Solvent mg/mL mM
Solubility
DMSO 80.0 197.80
Ethanol 80.0 197.80
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 404.45 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:
In vitro protocol:
1. Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Qun L, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Pharmacological profile of ipragliflozin (ASP1941), a novel selective SGLT2 inhibitor, in vitro and in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36. doi: 10.1007/s00210-011-0713-z. Epub 2011 Dec 3. PMID: 22139434.
In vivo protocol:
1. Imamura M, Nakanishi K, Suzuki T, Ikegai K, Shiraki R, Ogiyama T, Murakami T, Kurosaki E, Noda A, Kobayashi Y, Yokota M, Koide T, Kosakai K, Ohkura Y, Takeuchi M, Tomiyama H, Ohta M. Discovery of Ipragliflozin (ASP1941): a novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus. Bioorg Med Chem. 2012 May 15;20(10):3263-79. doi: 10.1016/j.bmc.2012.03.051. Epub 2012 Mar 29. PMID: 22507206. 2. Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Qun L, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Pharmacological profile of ipragliflozin (ASP1941), a novel selective SGLT2 inhibitor, in vitro and in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36. doi: 10.1007/s00210-011-0713-z. Epub 2011 Dec 3. PMID: 22139434.
21: Kashiwagi A, Kazuta K, Goto K, Yoshida S, Ueyama E, Utsuno A. Ipragliflozin in combination with metformin for the treatment of Japanese patients with type 2 diabetes: ILLUMINATE, a randomized, double-blind, placebo-controlled study. Diabetes Obes Metab. 2015 Mar;17(3):304-8. doi: 10.1111/dom.12331. Epub 2014 Jul 31. PubMed PMID: 24919820; PubMed Central PMCID: PMC4342773. 22: Poole RM, Dungo RT. Ipragliflozin: first global approval. Drugs. 2014 Apr;74(5):611-7. doi: 10.1007/s40265-014-0204-x. PubMed PMID: 24668021. 23: Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Li Q, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Effects of sodium-glucose cotransporter 2 selective inhibitor ipragliflozin on hyperglycaemia, oxidative stress, inflammation and liver injury in streptozotocin-induced type 1 diabetic rats. J Pharm Pharmacol. 2014 Jul;66(7):975-87. doi: 10.1111/jphp.12223. Epub 2014 Feb 17. PubMed PMID: 24533859. 24: Yokono M, Takasu T, Hayashizaki Y, Mitsuoka K, Kihara R, Muramatsu Y, Miyoshi S, Tahara A, Kurosaki E, Li Q, Tomiyama H, Sasamata M, Shibasaki M, Uchiyama Y. SGLT2 selective inhibitor ipragliflozin reduces body fat mass by increasing fatty acid oxidation in high-fat diet-induced obese rats. Eur J Pharmacol. 2014 Mar 15;727:66-74. doi: 10.1016/j.ejphar.2014.01.040. Epub 2014 Jan 30. PubMed PMID: 24486393. 25: Zhang W, Smulders R, Abeyratne A, Dietz A, Krauwinkel W, Kadokura T, Keirns J. Ipragliflozin does not prolong QTc interval in healthy male and female subjects: a phase I study. Clin Ther. 2013 Aug;35(8):1150-1161.e3. doi: 10.1016/j.clinthera.2013.06.009. Epub 2013 Aug 2. PubMed PMID: 23910665. 26: Zhang W, Krauwinkel WJ, Keirns J, Townsend RW, Lasseter KC, Plumb L, Kadokura T, Ushigome F, Smulders R. The effect of moderate hepatic impairment on the pharmacokinetics of ipragliflozin, a novel sodium glucose co-transporter 2 (SGLT2) inhibitor. Clin Drug Investig. 2013 Jul;33(7):489-96. doi: 10.1007/s40261-013-0089-6. PubMed PMID: 23733389. 27: Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Li Q, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Effects of SGLT2 selective inhibitor ipragliflozin on hyperglycemia, hyperlipidemia, hepatic steatosis, oxidative stress, inflammation, and obesity in type 2 diabetic mice. Eur J Pharmacol. 2013 Sep 5;715(1-3):246-55. doi: 10.1016/j.ejphar.2013.05.014. Epub 2013 May 23. PubMed PMID: 23707905. 28: Kurosaki E, Ogasawara H. Ipragliflozin and other sodium-glucose cotransporter-2 (SGLT2) inhibitors in the treatment of type 2 diabetes: preclinical and clinical data. Pharmacol Ther. 2013 Jul;139(1):51-9. doi: 10.1016/j.pharmthera.2013.04.003. Epub 2013 Apr 4. Review. PubMed PMID: 23563279. 29: Fonseca VA, Ferrannini E, Wilding JP, Wilpshaar W, Dhanjal P, Ball G, Klasen S. Active- and placebo-controlled dose-finding study to assess the efficacy, safety, and tolerability of multiple doses of ipragliflozin in patients with type 2 diabetes mellitus. J Diabetes Complications. 2013 May-Jun;27(3):268-73. doi: 10.1016/j.jdiacomp.2012.11.005. Epub 2012 Dec 29. PubMed PMID: 23276620. 30: Wilding JP, Ferrannini E, Fonseca VA, Wilpshaar W, Dhanjal P, Houzer A. Efficacy and safety of ipragliflozin in patients with type 2 diabetes inadequately controlled on metformin: a dose-finding study. Diabetes Obes Metab. 2013 May;15(5):403-9. doi: 10.1111/dom.12038. Epub 2012 Dec 7. PubMed PMID: 23163880. 31: Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Qun L, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Antidiabetic effects of SGLT2-selective inhibitor ipragliflozin in streptozotocin-nicotinamide-induced mildly diabetic mice. J Pharmacol Sci. 2012;120(1):36-44. Epub 2012 Aug 23. PubMed PMID: 22971845. 32: Veltkamp SA, van Dijk J, Collins C, van Bruijnsvoort M, Kadokura T, Smulders RA. Combination treatment with ipragliflozin and metformin: a randomized, double-blind, placebo-controlled study in patients with type 2 diabetes mellitus. Clin Ther. 2012 Aug;34(8):1761-71. doi: 10.1016/j.clinthera.2012.06.027. Epub 2012 Jul 15. PubMed PMID: 22795925. 33: Smulders RA, Zhang W, Veltkamp SA, van Dijk J, Krauwinkel WJ, Keirns J, Kadokura T. No pharmacokinetic interaction between ipragliflozin and sitagliptin, pioglitazone, or glimepiride in healthy subjects. Diabetes Obes Metab. 2012 Oct;14(10):937-43. doi: 10.1111/j.1463-1326.2012.01624.x. Epub 2012 Jun 7. PubMed PMID: 22587345. 34: Imamura M, Nakanishi K, Suzuki T, Ikegai K, Shiraki R, Ogiyama T, Murakami T, Kurosaki E, Noda A, Kobayashi Y, Yokota M, Koide T, Kosakai K, Ohkura Y, Takeuchi M, Tomiyama H, Ohta M. Discovery of Ipragliflozin (ASP1941): a novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus. Bioorg Med Chem. 2012 May 15;20(10):3263-79. doi: 10.1016/j.bmc.2012.03.051. Epub 2012 Mar 29. PubMed PMID: 22507206. 35: Tahara A, Kurosaki E, Yokono M, Yamajuku D, Kihara R, Hayashizaki Y, Takasu T, Imamura M, Qun L, Tomiyama H, Kobayashi Y, Noda A, Sasamata M, Shibasaki M. Pharmacological profile of ipragliflozin (ASP1941), a novel selective SGLT2 inhibitor, in vitro and in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36. doi: 10.1007/s00210-011-0713-z. Epub 2011 Dec 3. PubMed PMID: 22139434. 36: Veltkamp SA, Kadokura T, Krauwinkel WJ, Smulders RA. Effect of Ipragliflozin (ASP1941), a novel selective sodium-dependent glucose co-transporter 2 inhibitor, on urinary glucose excretion in healthy subjects. Clin Drug Investig. 2011 Dec 1;31(12):839-51. doi: 10.2165/11594330-000000000-00000. PubMed PMID: 21877761. 37: Schwartz SL, Akinlade B, Klasen S, Kowalski D, Zhang W, Wilpshaar W. Safety, pharmacokinetic, and pharmacodynamic profiles of ipragliflozin (ASP1941), a novel and selective inhibitor of sodium-dependent glucose co-transporter 2, in patients with type 2 diabetes mellitus. Diabetes Technol Ther. 2011 Dec;13(12):1219-27. doi: 10.1089/dia.2011.0012. Epub 2011 Aug 19. PubMed PMID: 21854192.

View History

Gramicidin A

Gramicidin A

New Featured