Fidarestat
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Hodoodo CAT#: H319878

CAS#: 136087-85-9

Description: Fidarestat, also known as SNK-860 and SK-860, is a potent and promising Aldose Reductase Inhibitor. Administration of fidarestat after breakfast was effective in significantly alleviating some symptoms of diabetic polyneuropathy. Long-term treatment with SNK-860 has a beneficial preventive effect on the development of experimental diabetic neuropathy. Fidarestat is also a Promising Drug Targeting Autophagy in Colorectal Carcinoma.

Chemical Structure

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Fidarestat
CAS# 136087-85-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H319878
Name: Fidarestat
CAS#: 136087-85-9
Chemical Formula: C12H10FN3O4
Exact Mass: 279.07
Molecular Weight: 279.227
Elemental Analysis: C, 51.62; H, 3.61; F, 6.80; N, 15.05; O, 22.92

Price and Availability

Size Price Availability Quantity
5mg USD 450 2 Weeks
10mg USD 750 2 Weeks
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Synonym: SNK860; SNK-860; SNK 860; SK860; SK-860; SK 860; Fidarestat; Aldos.

IUPAC/Chemical Name: (2S,4S)-6-fluoro-2',5'-dioxospiro[chromane-4,4'-imidazolidine]-2-carboxamide

InChi Key: WAAPEIZFCHNLKK-UFBFGSQYSA-N

InChi Code: InChI=1S/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12-/m0/s1

SMILES Code: O=C([C@@H]1C[C@@](NC2=O)(C(N2)=O)C3=C(O1)C=CC(F)=C3)N

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:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 279.23 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:
In vivo protocol:

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1: Pandey S. Aldose Reductase Inhibitor Fidarestat as a Promising Drug Targeting Autophagy in Colorectal Carcinoma: a Pilot Study. Asian Pac J Cancer Prev. 2015;16(12):4981-5. PubMed PMID: 26163626.

2: Talluri MV, Khatoon L, Kalariya PD, Chavan BB, Ragampeta S. LC-MS-MS Characterization of Forced Degradation Products of Fidarestat, a Novel Aldose Reductase Inhibitor: Development and Validation of a Stability-Indicating RP-HPLC Method. J Chromatogr Sci. 2015 Oct;53(9):1588-96. doi: 10.1093/chromsci/bmv061. Epub 2015 May 25. PubMed PMID: 26014964.

3: Borkar RM, Bhandi MM, Dubey AP, Nandekar PP, Sangamwar AT, Banerjee SK, Srinivas R. Plasma protein binding, pharmacokinetics, tissue distribution and CYP450 biotransformation studies of fidarestat by ultra high performance liquid chromatography-high resolution mass spectrometry. J Pharm Biomed Anal. 2015 Jan;102:386-99. doi: 10.1016/j.jpba.2014.10.008. Epub 2014 Oct 19. PubMed PMID: 25459938.

4: Ruiz FX, Cousido-Siah A, Mitschler A, Farrés J, Parés X, Podjarny A. X-ray structure of the V301L aldo-keto reductase 1B10 complexed with NADP(+) and the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. Chem Biol Interact. 2013 Feb 25;202(1-3):178-85. doi: 10.1016/j.cbi.2012.12.013. Epub 2013 Jan 4. PubMed PMID: 23295227.

5: Takahashi K, Mizukami H, Kamata K, Inaba W, Kato N, Hibi C, Yagihashi S. Amelioration of acute kidney injury in lipopolysaccharide-induced systemic inflammatory response syndrome by an aldose reductase inhibitor, fidarestat. PLoS One. 2012;7(1):e30134. doi: 10.1371/journal.pone.0030134. Epub 2012 Jan 12. PubMed PMID: 22253906; PubMed Central PMCID: PMC3257265.

6: Obrosova IG, Maksimchyk Y, Pacher P, Agardh E, Smith ML, El-Remessy AB, Agardh CD. Evaluation of the aldose reductase inhibitor fidarestat on ischemia-reperfusion injury in rat retina. Int J Mol Med. 2010 Jul;26(1):135-42. PubMed PMID: 20514433; PubMed Central PMCID: PMC3044435.

7: Hattori T, Matsubara A, Taniguchi K, Ogura Y. Aldose reductase inhibitor fidarestat attenuates leukocyte-endothelial interactions in experimental diabetic rat retina in vivo. Curr Eye Res. 2010 Feb;35(2):146-54. doi: 10.3109/02713680903447918. PubMed PMID: 20136425.

8: Agardh CD, Agardh E, Obrosova IG, Smith ML. The aldose reductase inhibitor fidarestat suppresses ischemia-reperfusion-induced inflammatory response in rat retina. Pharmacology. 2009;84(5):257-63. doi: 10.1159/000241733. Epub 2009 Sep 24. PubMed PMID: 19776662.

9: Fournier B, Bendeif el-E, Guillot B, Podjarny A, Lecomte C, Jelsch C. Charge density and electrostatic interactions of fidarestat, an inhibitor of human aldose reductase. J Am Chem Soc. 2009 Aug 12;131(31):10929-41. doi: 10.1021/ja8095015. PubMed PMID: 19594152.

10: Drel VR, Pacher P, Ali TK, Shin J, Julius U, El-Remessy AB, Obrosova IG. Aldose reductase inhibitor fidarestat counteracts diabetes-associated cataract formation, retinal oxidative-nitrosative stress, glial activation, and apoptosis. Int J Mol Med. 2008 Jun;21(6):667-76. PubMed PMID: 18506358; PubMed Central PMCID: PMC2527815.

11: Zhao HT, Hazemann I, Mitschler A, Carbone V, Joachimiak A, Ginell S, Podjarny A, El-Kabbani O. Unusual binding mode of the 2S4R stereoisomer of the potent aldose reductase cyclic imide inhibitor fidarestat (2S4S) in the 15 K crystal structure of the ternary complex refined at 0.78 A resolution: implications for the inhibition mechanism. J Med Chem. 2008 Mar 13;51(5):1478-81. doi: 10.1021/jm701514k. Epub 2008 Feb 20. PubMed PMID: 18284183.

12: Dong F, Ren J. Fidarestat improves cardiomyocyte contractile function in db/db diabetic obese mice through a histone deacetylase Sir2-dependent mechanism. J Hypertens. 2007 Oct;25(10):2138-47. PubMed PMID: 17885559.

13: Hotta N, Yasuda K, Sumita Y, Sano T, Kakuta H, Nagashima M, Hayashi Y, Yamamoto M, Wakao T, Okuyama M, Kobayashi M, Mori K. Effects of a Novel Aldose Reductase Inhibitor, Fidarestat (SNK-860), on Vibration Perception Threshold and Subjective Symptoms in Patients with Diabetic Polyneuropathy : An Open-Label Pilot Study. Clin Drug Investig. 2004;24(11):671-80. PubMed PMID: 17523730.

14: Zotova EG, Christ GJ, Zhao W, Tar M, Kuppam SD, Arezzo JC. Effects of fidarestat, an aldose reductase inhibitor, on nerve conduction velocity and bladder function in streptozotocin-treated female rats. J Diabetes Complications. 2007 May-Jun;21(3):187-95. PubMed PMID: 17493553.

15: Kuzumoto Y, Kusunoki S, Kato N, Kihara M, Low PA. Effect of the aldose reductase inhibitor fidarestat on experimental diabetic neuropathy in the rat. Diabetologia. 2006 Dec;49(12):3085-93. Epub 2006 Oct 25. PubMed PMID: 17063327.

16: Petrova T, Steuber H, Hazemann I, Cousido-Siah A, Mitschler A, Chung R, Oka M, Klebe G, El-Kabbani O, Joachimiak A, Podjarny A. Factorizing selectivity determinants of inhibitor binding toward aldose and aldehyde reductases: structural and thermodynamic properties of the aldose reductase mutant Leu300Pro-fidarestat complex. J Med Chem. 2005 Sep 8;48(18):5659-65. PubMed PMID: 16134934.

17: El-Kabbani O, Carbone V, Darmanin C, Oka M, Mitschler A, Podjarny A, Schulze-Briese C, Chung RP. Structure of aldehyde reductase holoenzyme in complex with the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. J Med Chem. 2005 Aug 25;48(17):5536-42. PubMed PMID: 16107153.

18: Asano T, Saito Y, Kawakami M, Yamada N, Sekino H, Hasegawa S; Fidarestat Clinical Pharmacology Study Group. Erythrocytic sorbitol contents in diabetic patients correlate with blood aldose reductase protein contents and plasma glucose levels, and are normalized by the potent aldose reductase inhibitor fidarestat (SNK-860). J Diabetes Complications. 2004 Nov-Dec;18(6):336-42. PubMed PMID: 15531183.

19: El-Kabbani O, Darmanin C, Oka M, Schulze-Briese C, Tomizaki T, Hazemann I, Mitschler A, Podjarny A. High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor Fidarestat: stereospecific interaction between the enzyme and a cyclic imide type inhibitor. J Med Chem. 2004 Aug 26;47(18):4530-7. PubMed PMID: 15317464.

20: Yorek MA, Coppey LJ, Gellett JS, Davidson EP, Lund DD. Effect of fidarestat and alpha-lipoic acid on diabetes-induced epineurial arteriole vascular dysfunction. Exp Diabesity Res. 2004 Apr-Jun;5(2):123-35. PubMed PMID: 15203883; PubMed Central PMCID: PMC2496880.