SX 3202 | CAS#147254-65-7 | inhibitor

MedKoo Cat#: 585126 | Name: SX 3202

Description:

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

SX 3202 is an aldose reductase inhibitor being developed for the treatment of diabetic neuropathy.

Chemical Structure

SX 3202

CAS#147254-65-7

Theoretical Analysis

MedKoo Cat#: 585126

Name: SX 3202

CAS#: 147254-65-7

Chemical Formula: C17H11BrFN3O4

Exact Mass: 418.9917

Molecular Weight: 420.19

Elemental Analysis: C, 48.59; H, 2.64; Br, 19.02; F, 4.52; N, 10.00; O, 15.23

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

SX 3202; Ranirestat; AS-3201; SX-3030

IUPAC/Chemical Name

Spiro(pyrrolidine-3,4'(1'H)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'H)-tetrone, 2'-((4-bromo-2-fluorophenyl)methyl)-, (3'S)-

InChi Key

QCVNMNYRNIMDKV-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H11BrFN3O4/c18-10-4-3-9(11(19)6-10)8-21-14(24)12-2-1-5-22(12)17(16(21)26)7-13(23)20-15(17)25/h1-6H,7-8H2,(H,20,23,25)

SMILES Code

O=C(N(CC1=CC=C(Br)C=C1F)C2=O)C3=CC=CN3C2(C4)C(NC4=O)=O

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 420.19 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.

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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PubMed PMID: 26313450. 5: Satoh J, Kohara N, Sekiguchi K, Yamaguchi Y. Effect of Ranirestat on Sensory and Motor Nerve Function in Japanese Patients with Diabetic Polyneuropathy: A Randomized Double-Blind Placebo-Controlled Study. J Diabetes Res. 2016;2016:5383797. doi: 10.1155/2016/5383797. Epub 2016 Jan 10. PubMed PMID: 26881251; PubMed Central PMCID: PMC4736957. 6: Ishibashi Y, Matsui T, Matsumoto T, Kato H, Yamagishi S. Ranirestat has a stronger inhibitory activity on aldose reductase and suppresses inflammatory reactions in high glucose-exposed endothelial cells. Diab Vasc Dis Res. 2016 Jul;13(4):312-5. doi: 10.1177/1479164116640220. Epub 2016 Apr 29. PubMed PMID: 27190083. 7: Miyoshi A, Yamada M, Shida H, Nakazawa D, Kusunoki Y, Nakamura A, Miyoshi H, Tomaru U, Atsumi T, Ishizu A. Circulating Neutrophil Extracellular Trap Levels in Well-Controlled Type 2 Diabetes and Pathway Involved in Their Formation Induced by High-Dose Glucose. Pathobiology. 2016;83(5):243-51. doi: 10.1159/000444881. Epub 2016 May 18. PubMed PMID: 27189166. 8: Toyoda F, Tanaka Y, Ota A, Shimmura M, Kinoshita N, Takano H, Matsumoto T, Tsuji J, Kakehashi A. Effect of ranirestat, a new aldose reductase inhibitor, on diabetic retinopathy in SDT rats. J Diabetes Res. 2014;2014:672590. doi: 10.1155/2014/672590. Epub 2014 Aug 25. PubMed PMID: 25215304; PubMed Central PMCID: PMC4158328. 9: Sekiguchi K, Kohara N, Baba M, Komori T, Naito Y, Imai T, Satoh J, Yamaguchi Y, Hamatani T; Ranirestat Group. Aldose reductase inhibitor ranirestat significantly improves nerve conduction velocity in diabetic polyneuropathy: A randomized double-blind placebo-controlled study in Japan. J Diabetes Investig. 2019 Mar;10(2):466-474. doi: 10.1111/jdi.12890. Epub 2018 Aug 9. PubMed PMID: 29975462; PubMed Central PMCID: PMC6400176. 10: Giannoukakis N. Ranirestat as a therapeutic aldose reductase inhibitor for diabetic complications. Expert Opin Investig Drugs. 2008 Apr;17(4):575-81. doi: 10.1517/13543784.17.4.575 . Review. PubMed PMID: 18363521. 11: Yamamura ET, Tsuzaki K, Kita S. A novel method of producing the key intermediate ASI-2 of ranirestat using a porcine liver esterase (PLE) substitute enzyme. Biosci Biotechnol Biochem. 2019 Jun;83(6):1124-1135. doi: 10.1080/09168451.2019.1580139. Epub 2019 Feb 20. PubMed PMID: 30782084. 12: Schemmel KE, Padiyara RS, D'Souza JJ. Aldose reductase inhibitors in the treatment of diabetic peripheral neuropathy: a review. J Diabetes Complications. 2010 Sep-Oct;24(5):354-60. doi: 10.1016/j.jdiacomp.2009.07.005. Epub 2009 Sep 11. Review. PubMed PMID: 19748287. 13: Antony P, Vijayan R. Identification of Novel Aldose Reductase Inhibitors from Spices: A Molecular Docking and Simulation Study. PLoS One. 2015 Sep 18;10(9):e0138186. doi: 10.1371/journal.pone.0138186. eCollection 2015. PubMed PMID: 26384019; PubMed Central PMCID: PMC4575143. 14: Várkonyi T, Kempler P. Diabetic neuropathy: new strategies for treatment. Diabetes Obes Metab. 2008 Feb;10(2):99-108. Epub 2007 Jun 26. Review. PubMed PMID: 17593238. 15: Ota A, Kakehashi A, Toyoda F, Kinoshita N, Shinmura M, Takano H, Obata H, Matsumoto T, Tsuji J, Dobashi Y, Fujimoto WY, Kawakami M, Kanazawa Y. Effects of long-term treatment with ranirestat, a potent aldose reductase inhibitor, on diabetic cataract and neuropathy in spontaneously diabetic torii rats. J Diabetes Res. 2013;2013:175901. doi: 10.1155/2013/175901. Epub 2013 Mar 13. PubMed PMID: 23671855; PubMed Central PMCID: PMC3647549. 16: Negoro T, Murata M, Ueda S, Fujitani B, Ono Y, Kuromiya A, Komiya M, Suzuki K, Matsumoto J. Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine -4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners. J Med Chem. 1998 Oct 8;41(21):4118-29. PubMed PMID: 9767647. 17: Shibasaki M, Kumagai N, Mashiko T. Inventing and understanding catalytic, enantioselective reactions. Curr Opin Drug Discov Devel. 2009 Nov;12(6):862-75. Review. PubMed PMID: 19894195. 18: Bril V, Hirose T, Tomioka S, Buchanan R; Ranirestat Study Group. Ranirestat for the management of diabetic sensorimotor polyneuropathy. Diabetes Care. 2009 Jul;32(7):1256-60. doi: 10.2337/dc08-2110. Epub 2009 Apr 14. PubMed PMID: 19366965; PubMed Central PMCID: PMC2699746. 19: Kurono M, Fujiwara I, Yoshida K. Stereospecific interaction of a novel spirosuccinimide type aldose reductase inhibitor, AS-3201, with aldose reductase. Biochemistry. 2001 Jul 27;40(28):8216-26. PubMed PMID: 11444967. 20: Giannoukakis N. Drug evaluation: ranirestat--an aldose reductase inhibitor for the potential treatment of diabetic complications. Curr Opin Investig Drugs. 2006 Oct;7(10):916-23. Review. PubMed PMID: 17086937.