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

MedKoo CAT#: 526592

CAS#: 110703-94-1

Description: Zopolrestat is a aldose reductase inhibitor potentially for the treatment of diabetic nephropathy and diabetes.


Price and Availability

Size
Price

10mg
USD 190
Size
Price

20mg
USD 350
Size
Price

50mg
USD 750

Zopolrestat, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526592
Name: Zopolrestat
CAS#: 110703-94-1
Chemical Formula: C19H12F3N3O3S
Exact Mass: 419.0551
Molecular Weight: 419.3782
Elemental Analysis: C, 54.42; H, 2.88; F, 13.59; N, 10.02; O, 11.44; S, 7.64


Synonym: CP 73850; CP73850; CP-73850; Zopolrestat; Zopolrestatum

IUPAC/Chemical Name: 2-(4-oxo-3-((5-(trifluoromethyl)benzo[d]thiazol-2-yl)methyl)-3,4-dihydrophthalazin-1-yl)acetic acid

InChi Key: BCSVCWVQNOXFGL-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H12F3N3O3S/c20-19(21,22)10-5-6-15-14(7-10)23-16(29-15)9-25-18(28)12-4-2-1-3-11(12)13(24-25)8-17(26)27/h1-7H,8-9H2,(H,26,27)

SMILES Code: O=C(O)CC1=NN(CC2=NC3=CC(C(F)(F)F)=CC=C3S2)C(C4=C1C=CC=C4)=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, 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).

Harmonized System Code:
293490


References

1: Bouguerra G, Bissinger R, Abbès S, Lang F. Zopolrestat Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2015;37(4):1537-46. doi: 10.1159/000438521. Epub 2015 Oct 30. PubMed PMID: 26512879.

2: Zhai J, Zhang H, Zhang L, Zhao Y, Chen S, Chen Y, Peng X, Li Q, Yuan M, Hu X. Zopolrestat as a human glyoxalase I inhibitor and its structural basis. ChemMedChem. 2013 Sep;8(9):1462-4. doi: 10.1002/cmdc.201300243. Epub 2013 Jul 15. PubMed PMID: 23857942.

3: Badawy D, El-Bassossy HM, Fahmy A, Azhar A. Aldose reductase inhibitors zopolrestat and ferulic acid alleviate hypertension associated with diabetes: effect on vascular reactivity. Can J Physiol Pharmacol. 2013 Feb;91(2):101-7. doi: 10.1139/cjpp-2012-0232. Epub 2013 Feb 11. PubMed PMID: 23458193.

4: Ramasamy R, Liu H, Oates PJ, Schaefer S. Attenuation of ischemia induced increases in sodium and calcium by the aldose reductase inhibitor zopolrestat. Cardiovasc Res. 1999 Apr;42(1):130-9. PubMed PMID: 10435004.

5: Beyer-Mears A, Mistry K, Diecke FP, Cruz E. Zopolrestat prevention of proteinuria, albuminuria and cataractogenesis in diabetes mellitus. Pharmacology. 1996 May;52(5):292-302. PubMed PMID: 8807673.

6: Inskeep PB, Reed AE, Ronfeld RA. Pharmacokinetics of zopolrestat, a carboxylic acid aldose reductase inhibitor, in normal and diabetic rats. Pharm Res. 1991 Dec;8(12):1511-5. PubMed PMID: 1808615.

7: Inskeep PB, Ronfeld RA, Peterson MJ, Gerber N. Pharmacokinetics of the aldose reductase inhibitor, zopolrestat, in humans. J Clin Pharmacol. 1994 Jul;34(7):760-6. PubMed PMID: 7929871.

8: Inskeep PB, Chin EB, Henry EW, Lazar JD, Conrad K, Reed AE, Ronfeld RA. The Effect of Urinary pH and Flow Rate on the Renal Elimination of Zopolrestat and Zopolrestat Glucuronide in Humans. Am J Ther. 1996 Mar;3(3):219-224. PubMed PMID: 11862253.

9: Schneider RP, Davenport CJ, Hoffmaster KA, Inskeep PB. Bioavailability, multiple-dose pharmacokinetics, and biotransformation of the aldose reductase inhibitor zopolrestat in dogs. Drug Metab Dispos. 1998 Nov;26(11):1160-6. PubMed PMID: 9806960.

10: El-Bassossy H, Badawy D, Neamatallah T, Fahmy A. Ferulic acid, a natural polyphenol, alleviates insulin resistance and hypertension in fructose fed rats: Effect on endothelial-dependent relaxation. Chem Biol Interact. 2016 Jun 7;254:191-197. doi: 10.1016/j.cbi.2016.06.013. [Epub ahead of print] PubMed PMID: 27287418.

11: Schneider RP, Fouda HG, Inskeep PB. Tissue distribution and biotransformation of zopolrestat, an aldose reductase inhibitor, in rats. Drug Metab Dispos. 1998 Nov;26(11):1149-59. PubMed PMID: 9806959.

12: Beyer-Mears A, Diecke FP, Mistry K, Cruz E. Comparison of the effects of Zopolrestat and Sorbinil on lens myo-inositol influx. Pharmacology. 1997 Feb;54(2):76-83. PubMed PMID: 9088040.

13: Carvalho VF, Barreto EO, Serra MF, Cordeiro RS, Martins MA, Fortes ZB, e Silva PM. Aldose reductase inhibitor zopolrestat restores allergic hyporesponsiveness in alloxan-diabetic rats. Eur J Pharmacol. 2006 Nov 7;549(1-3):173-8. Epub 2006 Aug 26. PubMed PMID: 16979157.

14: Inskeep PB, Reed AE, Connolly AG, Wilner KD, Vargas R, McMahon FG. Pharmacokinetics in Non-Insulin-Dependent Diabetics of the Aldose Reductase Inhibitor, Zopolrestat. Am J Ther. 1995 Feb;2(2):112-118. PubMed PMID: 11847537.

15: Mylari BL, Larson ER, Beyer TA, Zembrowski WJ, Aldinger CE, Dee MF, Siegel TW, Singleton DH. Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl] methyl]-1-phthalazineacetic acid (zopolrestat) and congeners. J Med Chem. 1991 Jan;34(1):108-22. PubMed PMID: 1899452.

16: Wilson DK, Tarle I, Petrash JM, Quiocho FA. Refined 1.8 A structure of human aldose reductase complexed with the potent inhibitor zopolrestat. Proc Natl Acad Sci U S A. 1993 Nov 1;90(21):9847-51. PubMed PMID: 8234324; PubMed Central PMCID: PMC47669.

17: Chen T, Shi D, Chen J, Yang Y, Qiu M, Wang W, Qiu L. Inhibition of aldose reductase ameliorates diet-induced nonalcoholic steatohepatitis in mice via modulating the phosphorylation of hepatic peroxisome proliferator-activated receptor α. Mol Med Rep. 2015 Jan;11(1):303-8. doi: 10.3892/mmr.2014.2713. Epub 2014 Oct 21. PubMed PMID: 25333350.

18: Mylari BL, Beyer TA, Scott PJ, Aldinger CE, Dee MF, Siegel TW, Zembrowski WJ. Potent, orally active aldose reductase inhibitors related to zopolrestat: surrogates for benzothiazole side chain. J Med Chem. 1992 Feb 7;35(3):457-65. PubMed PMID: 1738141.

19: Joseph D, Kimar C, Symington B, Milne R, Essop MF. The detrimental effects of acute hyperglycemia on myocardial glucose uptake. Life Sci. 2014 Jun 6;105(1-2):31-42. doi: 10.1016/j.lfs.2014.04.009. Epub 2014 Apr 18. PubMed PMID: 24747137.

20: Qiu L, Lin J, Xu F, Gao Y, Zhang C, Liu Y, Luo Y, Yang JY. Inhibition of aldose reductase activates hepatic peroxisome proliferator-activated receptor-α and ameliorates hepatosteatosis in diabetic db/db mice. Exp Diabetes Res. 2012;2012:789730. doi: 10.1155/2012/789730. Epub 2011 Nov 3. PubMed PMID: 22110479; PubMed Central PMCID: PMC3216305.