Sorbinil

Sorbinil
Names


IUPAC name (4S)-6-Fluoro-2,3-dihydro-2’H,5’H-spiro[chromene-4,4’-imidazolidine]-2’,5’-dione
Other names (S)-6-Fluorospiro(chroman-4,4'-imidazolidine)-2',5'-dione; CP 45634
Identifiers
CAS Number	68367-52-2
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL7681
ChemSpider	298991
ECHA InfoCard	100.210.173
IUPHAR/BPS	7415
KEGG	D05893
PubChem	337359
UNII	G4186B906P^Y
InChI 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 Fc3ccc2OCC[C@@]1(C(=O)NC(=O)N1)c2c3
Properties^[1]
Chemical formula	C₁₁H₉FN₂O₃
Molar mass	236.20 g·mol⁻¹
Appearance	White to off-white powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sorbinil (INN) is an aldose reductase inhibitor being investigated for treatment of diabetic complications including neuropathy and retinopathy.^[2] 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^[3] and placenta^[4] and calf^[5] and rat lens.^[4] Sorbinil reduced sorbitol accummulation in rat lens and sciatic nerve of diabetic rats orally administered 0.25 mg/kg sorbinil.^[4]

References

↑ Sorbinil at Sigma-Aldrich
↑ MacCari, R; Del Corso, A; Giglio, M; Moschini, R; Mura, U; Ottanà, R (2011). "In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors". Bioorganic & Medicinal Chemistry Letters. 21 (1): 200–3. doi:10.1016/j.bmcl.2010.11.041. PMID 21129963.
↑ O'Brien MM; et al. (1982). "Inhibition of human brain aldose reductase and hexonate dehydrogenase by alrestatin and sorbinil". J Neurochem. 39: 810–4. doi:10.1111/j.1471-4159.1982.tb07964.x. PMID 6808090.
1 2 3 Kinoshita JH; et al. (1979). "Aldose reductase in diabetic complications of the eye". Metabolism. 28 (suppl 1): 462–9. doi:10.1016/0026-0495(79)90057-x. PMID 45423.
↑ Peterson MJ; et al. (1979). "CP45,634: A novel aldose reductase inhibitor that inhibits polyol pathway activity in diabetic and galactosemic rats.". Metabolism. 39 (Suppl 1): 456–61. doi:10.1016/0026-0495(79)90056-8. PMID 122297.

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Biguanides	Buformin^‡ Metformin^# Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation: Glibenclamide (glyburide)^# Glibornuride Glicaramide Gliclazide Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide

Meglitinides/"glinides"	Mitiglinide Nateglinide Repaglinide

Analogs/other insulins

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ipragliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

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