sorbinil   Click here for help

GtoPdb Ligand ID: 7415

Synonyms: CP-45634
PDB Ligand
Compound class: Synthetic organic
Comment: Chemical structure is derived from [5]. Sorbinil is an experimental aldose reductase inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 67.43
Molecular weight 236.06
XLogP 1
No. Lipinski's rules broken 0
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Canonical SMILES Fc1cc2C3(CCOc2cc1)NC(=O)NC3=O
Isomeric SMILES Fc1cc2[C@]3(CCOc2cc1)NC(=O)NC3=O
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
1. Greene DA, Lattimer SA. (1984)
Action of sorbinil in diabetic peripheral nerve. Relationship of polyol (sorbitol) pathway inhibition to a myo-inositol-mediated defect in sodium-potassium ATPase activity.
Diabetes, 33 (8): 712-6. [PMID:6086432]
2. Jaspan J, Maselli R, Herold K, Bartkus C. (1983)
Treatment of severely painful diabetic neuropathy with an aldose reductase inhibitor: relief of pain and improved somatic and autonomic nerve function.
Lancet, 2 (8353): 758-62. [PMID:6137601]
3. 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.
Bioorg Med Chem Lett, 21 (1): 200-3. [PMID:21129963]
4. Oka M, Matsumoto Y, Sugiyama S, Tsuruta N, Matsushima M. (2000)
A potent aldose reductase inhibitor, (2S,4S)-6-fluoro-2', 5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (Fidarestat): its absolute configuration and interactions with the aldose reductase by X-ray crystallography.
J Med Chem, 43 (12): 2479-83. [PMID:10882376]
5. Sarges R, Bordner J, Dominy BW, Peterson MJ, Whipple EB. (1985)
Synthesis, absolute configuration, and conformation of the aldose reductase inhibitor sorbinil.
J Med Chem, 28 (11): 1716-20. [PMID:3934383]
6. Srivastava SK, Ramana KV, Bhatnagar A. (2005)
Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options.
Endocr Rev, 26 (3): 380-92. [PMID:15814847]
7. Young RJ, Ewing DJ, Clarke BF. (1983)
A controlled trial of sorbinil, an aldose reductase inhibitor, in chronic painful diabetic neuropathy.
Diabetes, 32 (10): 938-42. [PMID:6225686]