Zenarestat | CAS#112733-06-9

MedKoo Cat#: 526581 | Name: Zenarestat

Description:

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

Zenarestat, also known as CI-1014; FK-366; FR-74366, is an aldose reductase inhibitor. It was investigated as a treatment of diabetic neuropathy and cataract.

Chemical Structure

Zenarestat

CAS#112733-06-9

Theoretical Analysis

MedKoo Cat#: 526581

Name: Zenarestat

CAS#: 112733-06-9

Chemical Formula: C17H11BrClFN2O4

Exact Mass: 439.9575

Molecular Weight: 441.64

Elemental Analysis: C, 46.23; H, 2.51; Br, 18.09; Cl, 8.03; F, 4.30; N, 6.34; O, 14.49

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.

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Related CAS #

No Data

Synonym

FR 74366; FR74366 FR-74366; CI-1014; FK-366; CI1014; FK366; Zenarestat.

IUPAC/Chemical Name

2-(3-(4-bromo-2-fluorobenzyl)-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetic acid

InChi Key

SXONDGSPUVNZLO-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H11BrClFN2O4/c18-10-2-1-9(13(20)5-10)7-22-16(25)12-4-3-11(19)6-14(12)21(17(22)26)8-15(23)24/h1-6H,7-8H2,(H,23,24)

SMILES Code

O=C(O)CN1C(N(CC2=CC=C(Br)C=C2F)C(C3=C1C=C(Cl)C=C3)=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, 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 441.64 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

1: Zenarestat. FK 366, FR 74366, FR 901366. Drugs R D. 2002;3(4):235-7. Review. PubMed PMID: 12455199. 2: Kihara M, Mitsui Y, Shioyama M, Hasegawa T, Takahashi M, Takakura S, Minoura K, Kawamura I. Effect of zenarestat, an aldose reductase inhibitor, on endoneurial blood flow in experimental diabetic neuropathy of rat. Neurosci Lett. 2001 Sep 14;310(2-3):81-4. PubMed PMID: 11585572. 3: Shimoshige Y, Ikuma K, Yamamoto T, Takakura S, Kawamura I, Seki J, Mutoh S, Goto T. The effects of zenarestat, an aldose reductase inhibitor, on peripheral neuropathy in Zucker diabetic fatty rats. Metabolism. 2000 Nov;49(11):1395-9. PubMed PMID: 11092500. 4: Tanaka Y, Shimojyo H, Hata T, Hashimoto M, Noguchi H. Toxicokinetics of zenarestat, an aldose reductase inhibitor in animals and man. Xenobiotica. 1994 May;24(5):461-71. PubMed PMID: 8079505. 5: Greene DA, Arezzo JC, Brown MB. Effect of aldose reductase inhibition on nerve conduction and morphometry in diabetic neuropathy. Zenarestat Study Group. Neurology. 1999 Aug 11;53(3):580-91. Erratum in: Neurology 2001 Apr 24;56(8):1124. PubMed PMID: 10449124. 6: Tanaka Y, Sekiguchi M, Sawamoto T, Katami Y, Ueda T, Esumi Y, Noda K. Absorption, distribution and excretion of zenarestat, a new aldose reductase inhibitor, in rats and dogs. Xenobiotica. 1992 Jan;22(1):57-64. PubMed PMID: 1615708. 7: Tanaka Y, Kadoh Y, Mukumoto S, Ishikawa H. The role of age and sex hormones on the urinary excretion of zenarestat in rats. Xenobiotica. 1991 Oct;21(10):1273-9. PubMed PMID: 1796605. 8: Tanaka Y, Suzuki A. Enzymatic hydrolysis of zenarestat 1-O-acylglucuronide. J Pharm Pharmacol. 1994 Mar;46(3):235-9. PubMed PMID: 8027935. 9: Tanaka Y, Kadoh Y, Ishikawa H. Effects of hypophysectomy and testosterone treatment on the urinary excretion of zenarestat in rats. Xenobiotica. 1992 Jan;22(1):51-5. PubMed PMID: 1615707. 10: Yamamoto T, Takakura S, Kawamura I, Seki J, Goto T. The effects of zenarestat, an aldose reductase inhibitor, on minimal F-wave latency and nerve blood flow in streptozotocin-induced diabetic rats. Life Sci. 2001 Feb 9;68(12):1439-48. PubMed PMID: 11388695. 11: Tanaka Y, Sawamoto T, Suzuki A, Kimura T. Pharmacokinetics of zenarestat, an aldose reductase inhibitor, in male and female diabetic rats. Drug Metab Dispos. 1993 Jul-Aug;21(4):677-81. PubMed PMID: 8104128. 12: Kinoshita T, Miyake H, Fujii T, Takakura S, Goto T. The structure of human recombinant aldose reductase complexed with the potent inhibitor zenarestat. Acta Crystallogr D Biol Crystallogr. 2002 Apr;58(Pt 4):622-6. Epub 2002 Mar 22. PubMed PMID: 11914486. 13: Shimoshige Y, Minoura K, Matsuoka N, Takakura S, Mutoh S, Kamijo M. Thirteen-month inhibition of aldose reductase by zenarestat prevents morphological abnormalities in the dorsal root ganglia of streptozotocin-induced diabetic rats. Brain Res. 2009 Jan 9;1247:182-7. doi: 10.1016/j.brainres.2008.10.018. Epub 2008 Nov 1. PubMed PMID: 18992730. 14: Tanaka Y, Fujiwara T, Esumi Y. Sex difference in the excretion of zenarestat in mice, rats, dogs and humans. Xenobiotica. 1992 Aug;22(8):941-7. PubMed PMID: 1413883. 15: Tanaka Y, Deguchi Y, Ishii I, Terai T. Sex differences in excretion of zenarestat in rat. Xenobiotica. 1991 Sep;21(9):1119-25. PubMed PMID: 1788980. 16: Brown MJ, Bird SJ, Watling S, Kaleta H, Hayes L, Eckert S, Foyt HL; Zenarest study. Natural progression of diabetic peripheral neuropathy in the Zenarestat study population. Diabetes Care. 2004 May;27(5):1153-9. PubMed PMID: 15111537. 17: Shimoshige Y, Enomoto R, Aoki T, Matsuoka N, Kaneko S. The involvement of aldose reductase in alterations to neurotrophin receptors and neuronal cytoskeletal protein mRNA levels in the dorsal root ganglion of streptozotocin-induced diabetic rats. Biol Pharm Bull. 2010;33(1):67-71. PubMed PMID: 20045938. 18: Kato Y, Kuge K, Kusuhara H, Meier PJ, Sugiyama Y. Gender difference in the urinary excretion of organic anions in rats. J Pharmacol Exp Ther. 2002 Aug;302(2):483-9. PubMed PMID: 12130705. 19: Mizuno K, Kato N, Makino M, Suzuki T, Shindo M. Continuous inhibition of excessive polyol pathway flux in peripheral nerves by aldose reductase inhibitor fidarestat leads to improvement of diabetic neuropathy. J Diabetes Complications. 1999 May-Jun;13(3):141-50. PubMed PMID: 10509874. 20: 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. 2015;16(2):120-62. PubMed PMID: 26349493.