SX 3202

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

MedKoo CAT#: 585126

CAS#: 147254-65-7

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


Chemical Structure

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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: 420.1944
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 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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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

Preparing Stock Solutions

The following data is based on the product molecular weight 420.1944 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: Grewal AS, Bhardwaj S, Pandita D, Lather V, Sekhon BS. Updates on Aldose Reductase Inhibitors for Management of Diabetic Complications and Non-diabetic Diseases. Mini Rev Med Chem. 2016;16(2):120-62. Review. PubMed PMID: 26349493.

2: Hosseini A, Abdollahi M. Diabetic neuropathy and oxidative stress: therapeutic perspectives. Oxid Med Cell Longev. 2013;2013:168039. doi: 10.1155/2013/168039. Epub 2013 Apr 24. Review. PubMed PMID: 23738033; PubMed Central PMCID: PMC3655656.

3: Giannoukakis N. Evaluation of ranirestat for the treatment of diabetic neuropathy. Expert Opin Drug Metab Toxicol. 2014 Jul;10(7):1051-9. doi: 10.1517/17425255.2014.916277. Epub 2014 Apr 30. Review. PubMed PMID: 24785785.

4: Polydefkis M, Arezzo J, Nash M, Bril V, Shaibani A, Gordon RJ, Bradshaw KL, Junor RW; Ranirestat Study Group. Safety and efficacy of ranirestat in patients with mild-to-moderate diabetic sensorimotor polyneuropathy. J Peripher Nerv Syst. 2015 Dec;20(4):363-71. doi: 10.1111/jns.12138. 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.