Cemtirestat | CAS#309283-89-4 | aldose reductase inhibitor

MedKoo Cat#: 330239 | Name: Cemtirestat

Description:

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

Cemtirestat is a bifunctional drug acting as an aldose reductase inhibitor with antioxidant ability. Cemtirestat is considered a promising candidate for the treatment of diabetic neuropathy. Cemtirestat was found to scavenge reactive oxygen species (ROS) generated in water phase chemically with decreasing efficacy as follows ROO > H2O2 > O2-. Cemtirestat induces ocular defense against oxidative and inflammatory stress in rat models for glycotoxicity.

Chemical Structure

Cemtirestat

CAS#309283-89-4

Theoretical Analysis

MedKoo Cat#: 330239

Name: Cemtirestat

CAS#: 309283-89-4

Chemical Formula: C11H8N4O2S

Exact Mass: 260.0368

Molecular Weight: 260.27

Elemental Analysis: C, 50.76; H, 3.10; N, 21.53; O, 12.29; S, 12.32

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

Cemtirestat

IUPAC/Chemical Name

2,3-Dihydro-3-thioxo-5H-1,2,4-triazino[5,6-b]indole-5-acetic acid

InChi Key

LCMDWJXBUZDEKA-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H8N4O2S/c16-8(17)5-15-7-4-2-1-3-6(7)9-10(15)12-11(18)14-13-9/h1-4H,5H2,(H,16,17)(H,12,14,18)

SMILES Code

O=C(O)CN1C(C(C2=C1C=CC=C2)=NN3)=NC3=S

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

Peripheral neuropathy is the most prevalent chronic complication of diabetes mellitus. Good glycemic control can delay the appearance of neuropathic symptoms in diabetic patients but it is not sufficient to prevent or cure the disease. Therefore therapeutic approaches should focus on attenuation of pathogenetic mechanisms responsible for the nerve injur

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 260.27 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: Kaya A, Ceylan AF, Kavutcu M, Santamaria A, Šoltésová Prnová M, Stefek M, Karasu Ç. A dual-acting aldose reductase inhibitor impedes oxidative and carbonyl stress in tissues of fructose- and streptozotocin-induced rats: comparison with antioxidant stobadine. Drug Chem Toxicol. 2023 Oct 5:1-11. doi: 10.1080/01480545.2023.2262164. Epub ahead of print. PMID: 37795621. 2: Reihanifar T, Şahin M, Stefek M, Ceylan AF, Karasu Ç; Antioxidants in Diabetes-Induced Complications (ADIC) Study Group. Cemtirestat, an aldose reductase inhibitor and antioxidant compound, induces ocular defense against oxidative and inflammatory stress in rat models for glycotoxicity. Cell Biochem Funct. 2023 Aug;41(6):622-632. doi: 10.1002/cbf.3818. Epub 2023 Jun 5. PMID: 37272424. 3: Martiniakova M, Kovacova V, Mondockova V, Svik K, Londzin P, Folwarczna J, Soltesova Prnova M, Stefek M, Omelka R. The Effects of Prolonged Treatment with Cemtirestat on Bone Parameters Reflecting Bone Quality in Non-Diabetic and Streptozotocin-Induced Diabetic Rats. Pharmaceuticals (Basel). 2023 Apr 21;16(4):628. doi: 10.3390/ph16040628. PMID: 37111385; PMCID: PMC10145951. 4: Elmazoglu Z, Prnova MS, Stefek M, Ceylan AF, Aschner M, Rangel-López E, Santamaria A, Karasu C. Protective Effects of Novel Substituted Triazinoindole Inhibitors of Aldose Reductase and Epalrestat in Neuron-like PC12 Cells and BV2 Rodent Microglial Cells Exposed to Toxic Models of Oxidative Stress: Comparison with the Pyridoindole Antioxidant Stobadine. Neurotox Res. 2021 Jun;39(3):588-597. doi: 10.1007/s12640-021-00349-7. Epub 2021 Mar 13. PMID: 33713301. 5: Elmazoglu Z, Prnova MS, Santamaria A, Stefek M, Karasu C. Combatting Nitrosative Stress and Inflammation with Novel Substituted Triazinoindole Inhibitors of Aldose Reductase in PC12 Cells Exposed to 6-Hydroxydopamine Plus High Glucose. Neurotox Res. 2021 Apr;39(2):210-226. doi: 10.1007/s12640-020-00305-x. Epub 2020 Nov 4. PMID: 33146867. 6: Valachová K, Mach M, Šoltés L. Oxidative Degradation of High-Molar-Mass Hyaluronan: Effects of Some Indole Derivatives to Hyaluronan Decay. Int J Mol Sci. 2020 Aug 5;21(16):5609. doi: 10.3390/ijms21165609. PMID: 32764392; PMCID: PMC7460571. 7: Soltesova Prnova M, Medina-Campos ON, Pedraza-Chaverri J, Colín-González AL, Piedra-García F, Rangel-López E, Kovacikova L, Ceylan A, Karasu C, Santamaria A, Stefek M. Antioxidant Mechanisms in the Neuroprotective Action of Cemtirestat: Studies in Chemical Models, Liposomes and Rat Brain Cortical Slices. Neuroscience. 2020 Sep 1;443:206-217. doi: 10.1016/j.neuroscience.2020.07.014. Epub 2020 Jul 16. PMID: 32681927. 8: Prnová MŠ, Račková L, Kováčiková L, Balleková J, Viskupičová J, Micháliková S, Taşkoparan B, Elmazoğlu Z, Rižner TL, Karasu C, Banerjee S, Štefek M. General toxicity assessment of the novel aldose reductase inhibitor cemtirestat. Interdiscip Toxicol. 2019 Nov;12(3):120-128. doi: 10.2478/intox-2019-0014. Epub 2020 Feb 20. PMID: 32210700; PMCID: PMC7085302. 9: Hlaváč M, Kováčiková L, Prnová MŠ, Šramel P, Addová G, Májeková M, Hanquet G, Boháč A, Štefek M. Development of Novel Oxotriazinoindole Inhibitors of Aldose Reductase: Isosteric Sulfur/Oxygen Replacement in the Thioxotriazinoindole Cemtirestat Markedly Improved Inhibition Selectivity. J Med Chem. 2020 Jan 9;63(1):369-381. doi: 10.1021/acs.jmedchem.9b01747. Epub 2019 Dec 30. PMID: 31820975. 10: Prnova MS, Kovacikova L, Svik K, Bezek S, Elmazoğlu Z, Karasu C, Stefek M. Triglyceride-lowering effect of the aldose reductase inhibitor cemtirestat- another factor that may contribute to attenuation of symptoms of peripheral neuropathy in STZ-diabetic rats. Naunyn Schmiedebergs Arch Pharmacol. 2020 Apr;393(4):651-661. doi: 10.1007/s00210-019-01769-1. Epub 2019 Dec 5. PMID: 31802170. 11: Soltesova Prnova M, Svik K, Bezek S, Kovacikova L, Karasu C, Stefek M. 3-Mercapto-5H-1,2,4-Triazino[5,6-b]Indole-5-Acetic Acid (Cemtirestat) Alleviates Symptoms of Peripheral Diabetic Neuropathy in Zucker Diabetic Fatty (ZDF) Rats: A Role of Aldose Reductase. Neurochem Res. 2019 May;44(5):1056-1064. doi: 10.1007/s11064-019-02736-1. Epub 2019 Jan 28. PMID: 30689163. 12: Prnova MS, Ballekova J, Majekova M, Stefek M. Antioxidant action of 3-mercapto-5H-1,2,4-triazino[5,6-b]indole-5-acetic acid, an efficient aldose reductase inhibitor, in a 1,1'-diphenyl-2-picrylhydrazyl assay and in the cellular system of isolated erythrocytes exposed to tert-butyl hydroperoxide. Redox Rep. 2015;20(6):282-8. doi: 10.1179/1351000215Y.0000000019. Epub 2015 Jun 11. PMID: 26066740; PMCID: PMC6837688. 13: Stefek M, Soltesova Prnova M, Majekova M, Rechlin C, Heine A, Klebe G. Identification of novel aldose reductase inhibitors based on carboxymethylated mercaptotriazinoindole scaffold. J Med Chem. 2015 Mar 26;58(6):2649-57. doi: 10.1021/jm5015814. Epub 2015 Mar 4. PMID: 25695864.