T-1095A

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

MedKoo CAT#: 530635

CAS#: 209746-56-5

Description: T-1095A is an active metabolite of T-1095. T-1095 is a potent and selective inhibitor of Na+-glucose cotransporters (SGLTs). T-1095 may be a useful antidiabetic drug. Long-term treatment with T-1095 causes sustained improvement in hyperglycemia and prevents diabetic neuropathy in Goto-Kakizaki Rats. Chronic administration of T-1095 (0.1% w w(-1) pellet chow, for 12 weeks) decreased blood glucose and haemoglobin A(1C) levels, and improved glucose intolerance in db/db mice.


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T-1095A 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#: 530635
Name: T-1095A
CAS#: 209746-56-5
Chemical Formula: C24H26O9
Exact Mass: 458.1577
Molecular Weight: 458.463
Elemental Analysis: C, 62.88; H, 5.72; O, 31.41


Related CAS #: 209746-56-5 (T-1095A)   209746-59-8 (T-1095)  

Synonym: T-1095A, T 1095A, T1095A, J1.265.331J

IUPAC/Chemical Name: 3-(benzofuran-5-yl)-1-(2-hydroxy-4-methyl-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)propan-1-one

InChi Key: GMYFQAHYWIYNES-PFKOEMKTSA-N

InChi Code: InChI=1S/C24H26O9/c1-12-8-16(27)20(15(26)4-2-13-3-5-17-14(10-13)6-7-31-17)18(9-12)32-24-23(30)22(29)21(28)19(11-25)33-24/h3,5-10,19,21-25,27-30H,2,4,11H2,1H3/t19-,21-,22+,23-,24-/m1/s1

SMILES Code: O=C(CCC1=CC=C(OC=C2)C2=C1)C3=C(C=C(C=C3O[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)C)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

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: Yamaguchi K, Kato M, Ozawa K, Kawai T, Yata T, Aso Y, Ishigai M, Ikeda S. Pharmacokinetic and pharmacodynamic modeling for the effect of sodium-glucose cotransporter inhibitors on blood glucose level and renal glucose excretion in db/db mice. J Pharm Sci. 2012 Nov;101(11):4347-56. doi: 10.1002/jps.23302. Epub 2012 Aug 23. PubMed PMID: 22927193.

2: Nomura S, Sakamaki S, Hongu M, Kawanishi E, Koga Y, Sakamoto T, Yamamoto Y, Ueta K, Kimata H, Nakayama K, Tsuda-Tsukimoto M. Discovery of canagliflozin, a novel C-glucoside with thiophene ring, as sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes mellitus. J Med Chem. 2010 Sep 9;53(17):6355-60. doi: 10.1021/jm100332n. PubMed PMID: 20690635.

3: Nomura S. Renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for new anti-diabetic agent. Curr Top Med Chem. 2010;10(4):411-8. Review. PubMed PMID: 20180760.

4: von Lewinski D, Gasser R, Rainer PP, Huber MS, Wilhelm B, Roessl U, Haas T, Wasler A, Grimm M, Bisping E, Pieske B. Functional effects of glucose transporters in human ventricular myocardium. Eur J Heart Fail. 2010 Feb;12(2):106-13. doi: 10.1093/eurjhf/hfp191. PubMed PMID: 20083620.

5: Isaji M. Sodium-glucose cotransporter inhibitors for diabetes. Curr Opin Investig Drugs. 2007 Apr;8(4):285-92. Review. PubMed PMID: 17458177.

6: Fujimoto Y, Torres TP, Donahue EP, Shiota M. Glucose toxicity is responsible for the development of impaired regulation of endogenous glucose production and hepatic glucokinase in Zucker diabetic fatty rats. Diabetes. 2006 Sep;55(9):2479-90. PubMed PMID: 16936196.

7: Ueta K, Yoneda H, Oku A, Nishiyama S, Saito A, Arakawa K. Reduction of renal transport maximum for glucose by inhibition of NA(+)-glucose cotransporter suppresses blood glucose elevation in dogs. Biol Pharm Bull. 2006 Jan;29(1):114-8. PubMed PMID: 16394522.

8: Ueta K, Ishihara T, Matsumoto Y, Oku A, Nawano M, Fujita T, Saito A, Arakawa K. Long-term treatment with the Na+-glucose cotransporter inhibitor T-1095 causes sustained improvement in hyperglycemia and prevents diabetic neuropathy in Goto-Kakizaki Rats. Life Sci. 2005 Apr 22;76(23):2655-68. PubMed PMID: 15792833.

9: Asano T, Ogihara T, Katagiri H, Sakoda H, Ono H, Fujishiro M, Anai M, Kurihara H, Uchijima Y. Glucose transporter and Na+/glucose cotransporter as molecular targets of anti-diabetic drugs. Curr Med Chem. 2004 Oct;11(20):2717-24. Review. PubMed PMID: 15544472.

10: Saito A, Seiyaku T, Tsujihara K. [SGLT inhibitor (T-1095)]. Nihon Rinsho. 2002 Sep;60 Suppl 9:588-93. Review. Japanese. PubMed PMID: 12387055.

11: Nunoi K, Yasuda K, Adachi T, Okamoto Y, Shihara N, Uno M, Tamon A, Suzuki N, Oku A, Tsuda K. Beneficial effect of T-1095, a selective inhibitor of renal Na+-glucose cotransporters, on metabolic index and insulin secretion in spontaneously diabetic GK rats. Clin Exp Pharmacol Physiol. 2002 May-Jun;29(5-6):386-90. PubMed PMID: 12010180.

12: Yasuda K, Okamoto Y, Nunoi K, Adachi T, Shihara N, Tamon A, Suzuki N, Mukai E, Fujimoto S, Oku A, Tsuda K, Seino Y. Normalization of cytoplasmic calcium response in pancreatic beta-cells of spontaneously diabetic GK rat by the treatment with T-1095, a specific inhibitor of renal Na+-glucose co-transporters. Horm Metab Res. 2002 Apr;34(4):217-21. PubMed PMID: 11987033.

13: Oku A, Nawano M, Ueta K, Fujita T, Umebayashi I, Arakawa K, Kano-Ishihara T, Saito A, Anai M, Funaki M, Kikuchi M, Oka Y, Asano T. Inhibitory effect of hyperglycemia on insulin-induced Akt/protein kinase B activation in skeletal muscle. Am J Physiol Endocrinol Metab. 2001 May;280(5):E816-24. PubMed PMID: 11287365.

14: Arakawa K, Ishihara T, Oku A, Nawano M, Ueta K, Kitamura K, Matsumoto M, Saito A. Improved diabetic syndrome in C57BL/KsJ-db/db mice by oral administration of the Na(+)-glucose cotransporter inhibitor T-1095. Br J Pharmacol. 2001 Jan;132(2):578-86. PubMed PMID: 11159708; PubMed Central PMCID: PMC1572576.

15: Oku A, Ueta K, Arakawa K, Kano-Ishihara T, Matsumoto M, Adachi T, Yasuda K, Tsuda K, Saito A. Antihyperglycemic effect of T-1095 via inhibition of renal Na+-glucose cotransporters in streptozotocin-induced diabetic rats. Biol Pharm Bull. 2000 Dec;23(12):1434-7. PubMed PMID: 11145172.

16: Oku A, Ueta K, Arakawa K, Kano-Ishihara T, Matsumoto T, Adachi T, Yasuda K, Tsuda K, Ikezawa K, Saito A. Correction of hyperglycemia and insulin sensitivity by T-1095, an inhibitor of renal Na+-glucose cotransporters, in streptozotocin-induced diabetic rats. Jpn J Pharmacol. 2000 Nov;84(3):351-4. PubMed PMID: 11138738.

17: Adachi T, Yasuda K, Okamoto Y, Shihara N, Oku A, Ueta K, Kitamura K, Saito A, Iwakura I, Yamada Y, Yano H, Seino Y, Tsuda K. T-1095, a renal Na+-glucose transporter inhibitor, improves hyperglycemia in streptozotocin-induced diabetic rats. Metabolism. 2000 Aug;49(8):990-5. PubMed PMID: 10954015.

18: Oku A, Ueta K, Nawano M, Arakawa K, Kano-Ishihara T, Matsumoto M, Saito A, Tsujihara K, Anai M, Asano T. Antidiabetic effect of T-1095, an inhibitor of Na(+)-glucose cotransporter, in neonatally streptozotocin-treated rats. Eur J Pharmacol. 2000 Mar 10;391(1-2):183-92. PubMed PMID: 10720650.

19: Nawano M, Oku A, Ueta K, Umebayashi I, Ishirahara T, Arakawa K, Saito A, Anai M, Kikuchi M, Asano T. Hyperglycemia contributes insulin resistance in hepatic and adipose tissue but not skeletal muscle of ZDF rats. Am J Physiol Endocrinol Metab. 2000 Mar;278(3):E535-43. PubMed PMID: 10710509.

20: Nawano M, Ueta K, Oku A, Arakawa K, Saito A, Funaki M, Anai M, Kikuchi M, Oka Y, Asano T. Hyperglycemia impairs the insulin signaling step between PI 3-kinase and Akt/PKB activations in ZDF rat liver. Biochem Biophys Res Commun. 1999 Dec 9;266(1):252-6. PubMed PMID: 10581198.