Sorbinil | CP-45634 | CAS#68367-52-2 | aldose reductase inhibitor

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

MedKoo CAT#: 326986

CAS#: 68367-52-2

Description: Sorbinil, also known as CP-45634, is an aldose reductase inhibitor potentially for the treatment of diabetes. Aldose reductase is an enzyme present in lens and brain that gets rid of excess glucose by converting it to sorbitol. Sorbitol accumulation can lead to the development of cataracts in the lens and neuropathy in peripheral nerves. Sorbinil has been shown to inhibit aldose reductase in human brain and placenta and calf and rat lens. Sorbinil reduced sorbitol accummulation in rat lens and sciatic nerve of diabetic rats orally administered 0.25mg/kg sorbinil.

Chemical Structure

Sorbinil

CAS# 68367-52-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326986
Name: Sorbinil
CAS#: 68367-52-2
Chemical Formula: C11H9FN2O3
Exact Mass: 236.06
Molecular Weight: 236.200
Elemental Analysis: C, 55.94; H, 3.84; F, 8.04; N, 11.86; O, 20.32

Price and Availability

Size	Price	Availability
5mg	USD 350	2 Weeks
10mg	USD 575	2 Weeks
25mg	USD 900	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Sorbinil; CP-45634; CP 45634; CP45634.

IUPAC/Chemical Name: (S)-6-fluorospiro[chromane-4,4'-imidazolidine]-2',5'-dione

InChi Key: LXANPKRCLVQAOG-NSHDSACASA-N

InChi Code: InChI=1S/C11H9FN2O3/c12-6-1-2-8-7(5-6)11(3-4-17-8)9(15)13-10(16)14-11/h1-2,5H,3-4H2,(H2,13,14,15,16)/t11-/m0/s1

SMILES Code: O=C1N[C@@]2(C(N1)=O)CCOC3=CC=C(F)C=C23

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: >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

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Product Data:

Product Data

Instruction:

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Biological target:	Sorbinil prevents the accumulation of sorbitol in cells or animals.
In vitro activity:	AR inhibitors (ARIs), such as sorbinil and zopolrestat, could be promising agents for treating inflammation-related neurodegenerative diseases such as Alzheimer' disease. Sorbinil and zopolrestat significantly inhibit TNF-α, IL-1β, IL-6 production from microglia in response to Aβ stimulation. Sor and Zol decreased the production of intracellular ROS which resulted in an effective inhibition on the phosphorylation of several protein kinase C (PKC) isoforms including PKCα/β, δ, ζ/λ and mu. Reference: Int Immunopharmacol. 2017 Sep;50:30-37. https://pubmed.ncbi.nlm.nih.gov/28623716/
In vivo activity:	Sorbinil is an effective ARI, which could play therapeutic role in treating diabetes and diabetic complications. Animal model studies reported the efficacy of sorbinil in controlling the progression of diabetes. Moreover, sorbinil has been found to be comparatively safer than other ARIs for human use. Reference: Med Chem. 2019;15(1):3-7. https://pubmed.ncbi.nlm.nih.gov/29792152/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	423.37

Preparing Stock Solutions

The following data is based on the product molecular weight 236.20 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

Formulation protocol:	1. Song XM, Yu Q, Dong X, Yang HO, Zeng KW, Li J, Tu PF. Aldose reductase inhibitors attenuate β-amyloid-induced TNF-α production in microlgia via ROS-PKC-mediated NF-κB and MAPK pathways. Int Immunopharmacol. 2017 Sep;50:30-37. doi: 10.1016/j.intimp.2017.06.005. Epub 2017 Jun 15. PMID: 28623716. 2. Petrash JM, Shieh B, Ammar DA, Pedler MG, Orlicky DJ. Diabetes-Independent Retinal Phenotypes in an Aldose Reductase Transgenic Mouse Model. Metabolites. 2021 Jul 10;11(7):450. doi: 10.3390/metabo11070450. PMID: 34357344; PMCID: PMC8305400. 3. Huang Q, Liu Q, Ouyang D. Sorbinil, an Aldose Reductase Inhibitor, in Fighting Against Diabetic Complications. Med Chem. 2019;15(1):3-7. doi: 10.2174/1573406414666180524082445. PMID: 29792152.
In vitro protocol:	1. Song XM, Yu Q, Dong X, Yang HO, Zeng KW, Li J, Tu PF. Aldose reductase inhibitors attenuate β-amyloid-induced TNF-α production in microlgia via ROS-PKC-mediated NF-κB and MAPK pathways. Int Immunopharmacol. 2017 Sep;50:30-37. doi: 10.1016/j.intimp.2017.06.005. Epub 2017 Jun 15. PMID: 28623716.
In vivo protocol:	1. Petrash JM, Shieh B, Ammar DA, Pedler MG, Orlicky DJ. Diabetes-Independent Retinal Phenotypes in an Aldose Reductase Transgenic Mouse Model. Metabolites. 2021 Jul 10;11(7):450. doi: 10.3390/metabo11070450. PMID: 34357344; PMCID: PMC8305400. 2. Huang Q, Liu Q, Ouyang D. Sorbinil, an Aldose Reductase Inhibitor, in Fighting Against Diabetic Complications. Med Chem. 2019;15(1):3-7. doi: 10.2174/1573406414666180524082445. PMID: 29792152.

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1: Coppey LJ, Gellett JS, Davidson EP, Dunlap JA, Yorek MA. Effect of treating streptozotocin-induced diabetic rats with sorbinil, myo-inositol or aminoguanidine on endoneurial blood flow, motor nerve conduction velocity and vascular function of epineurial arterioles of the sciatic nerve. Int J Exp Diabetes Res. 2002;3(1):21-36. PubMed PMID: 11900277; PubMed Central PMCID: PMC2478566.

2: Sellers DJ, Chess-Williams R. The effect of sorbinil, an aldose reductase inhibitor, on aortic function in control and streptozotocin-induced diabetic rats. J Auton Pharmacol. 2000 Feb;20(1):15-22. PubMed PMID: 11048957.

3: Bohren KM, Grimshaw CE. The sorbinil trap: a predicted dead-end complex confirms the mechanism of aldose reductase inhibition. Biochemistry. 2000 Aug 15;39(32):9967-74. PubMed PMID: 10933817.

4: Sellers DJ, Chess-Williams R. The effects of streptozotocin-induced diabetes and aldose reductase inhibition with sorbinil, on left and right atrial function in the rat. J Pharm Pharmacol. 2000 Jun;52(6):687-94. PubMed PMID: 10875546.

5: Christen WG, Manson JE, Bubes V, Glynn RJ. Risk factors for progression of distal symmetric polyneuropathy in type 1 diabetes mellitus. Sorbinil Retinopathy Trial Research Group. Am J Epidemiol. 1999 Dec 1;150(11):1142-51. PubMed PMID: 10588075.

6: Karihaloo AK, Joshi K, Chopra JS. Effect of sorbinil and ascorbic acid on myo-inositol transport in cultured rat Schwann cells exposed to elevated extracellular glucose. J Neurochem. 1997 Nov;69(5):2011-8. PubMed PMID: 9349546.

7: Urzhumtsev A, Tête-Favier F, Mitschler A, Barbanton J, Barth P, Urzhumtseva L, Biellmann JF, Podjarny A, Moras D. A 'specificity' pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors tolrestat and sorbinil. Structure. 1997 May 15;5(5):601-12. PubMed PMID: 9195881.

8: 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.

9: Way KJ, Reid JJ. The aldose reductase inhibitor sorbinil does not prevent the impairment in nitric oxide-mediated neurotransmission in anococcygeus muscle from diabetic rats. Eur J Pharmacol. 1996 Dec 27;318(1):101-8. PubMed PMID: 9007520.

10: Malone JI, Lowitt S, Salem AF, Miranda C, Korthals JK, Carver J. The effects of acetyl-L-carnitine and sorbinil on peripheral nerve structure, chemistry, and function in experimental diabetes. Metabolism. 1996 Jul;45(7):902-7. PubMed PMID: 8692029.

11: Robison WG Jr, Laver NM, Jacot JL, Glover JP. Sorbinil prevention of diabetic-like retinopathy in the galactose-fed rat model. Invest Ophthalmol Vis Sci. 1995 Nov;36(12):2368-80. PubMed PMID: 7591626.

12: Edmands SD, Hughs KS, Lee SY, Meyer SD, Saari E, Yancey PH. Time-dependent aspects of osmolyte changes in rat kidney, urine, blood and lens with sorbinil and galactose feeding. Kidney Int. 1995 Aug;48(2):344-53. PubMed PMID: 7564101.

13: Pugliese G, Tilton RG, Speedy A, Oates PJ, Williamson JR. Effects of combined insulin and sorbinil treatment on diabetes-induced vascular dysfunction in rats. Metabolism. 1994 Apr;43(4):492-500. PubMed PMID: 8159110.

14: The sorbinil retinopathy trial: neuropathy results. Sorbinil Retinopathy Trial Research Group. Neurology. 1993 Jun;43(6):1141-9. PubMed PMID: 8170559.

15: Liu SQ, Bhatnagar A, Srivastava SK. Does sorbinil bind to the substrate binding site of aldose reductase? Biochem Pharmacol. 1992 Dec 15;44(12):2427-9. PubMed PMID: 1472112.

16: Sutera SP, Chang K, Marvel J, Williamson JR. Concurrent increases in regional hematocrit and blood flow in diabetic rats: prevention by sorbinil. Am J Physiol. 1992 Sep;263(3 Pt 2):H945-50. PubMed PMID: 1415621.

17: Körner A, Celsi G, Eklöf AC, Linné T, Persson B, Aperia A. Sorbinil does not prevent hyperfiltration, elevated ultrafiltration pressure and albuminuria in streptozotocin-diabetic rats. Diabetologia. 1992 May;35(5):414-8. PubMed PMID: 1521721.

18: Beyer-Mears A, Murray FT, Cruz E, Rountree J, Sciadini M. Comparison of sorbinil and ponalrestat (Statil) diminution of proteinuria in the BB rat. Pharmacology. 1992;45(5):285-91. PubMed PMID: 1465475.

19: Tilton RG, Pugliese G, LaRose LS, Faller AM, Chang K, Province MA, Williamson JR. Discordant effects of the aldose reductase inhibitor, sorbinil, on vascular structure and function in chronically diabetic and galactosemic rats. J Diabet Complications. 1991 Oct-Dec;5(4):230-7. PubMed PMID: 1779018.

20: Kato K, Nakayama K, Mizota M, Miwa I, Okuda J. Properties of novel aldose reductase inhibitors, M16209 and M16287, in comparison with known inhibitors, ONO-2235 and sorbinil. Chem Pharm Bull (Tokyo). 1991 Jun;39(6):1540-5. PubMed PMID: 1934175.

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