Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H9FN2O3 |
| Molecular Weight | 236.1992 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C2OCC[C@]3(NC(=O)NC3=O)C2=C1
InChI
InChIKey=LXANPKRCLVQAOG-NSHDSACASA-N
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
Sorbinil (also known as CP-45,634), an aldose reductase inhibitor that has been in phase III clinical trials in preventing the development of diabetic retinopathy and neuropathy in persons with insulin-dependent diabetes. However, this research has been discontinued. It is also known, that sorbinil is oxidatively metabolized to a potentially toxic intermediate.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.36 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
6.25 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
547 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
528 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
76.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
58.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3107606 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SORBINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2000 Jun 15 |
|
| Diabetes-induced changes in retinal NAD-redox status: pharmacological modulation and implications for pathogenesis of diabetic retinopathy. | 2001 |
|
| Identification of biochemical pathways for the metabolism of oxidized low-density lipoprotein derived aldehyde-4-hydroxy trans-2-nonenal in vascular smooth muscle cells. | 2001 Oct |
|
| Thiol/disulfide interconversion in bovine lens aldose reductase induced by intermediates of glutathione turnover. | 2001 Oct 9 |
|
| Glyceraldehyde metabolism in human erythrocytes in comparison with that of glucose and dihydroxyacetone. | 2002 Sep |
|
| Incorporation of clustering effects for the Wilcoxon rank sum test: a large-sample approach. | 2003 Dec |
|
| Aldose reductase inhibition in the treatment of diabetic neuropathy: where are we in 2004? | 2004 Dec |
|
| Aldose reductase regulates TNF-alpha-induced cell signaling and apoptosis in vascular endothelial cells. | 2004 Jul 16 |
|
| A potent sorbitol dehydrogenase inhibitor exacerbates sympathetic autonomic neuropathy in rats with streptozotocin-induced diabetes. | 2005 Apr |
|
| The biosynthesis of ascorbate protects isolated rat hepatocytes from cumene hydroperoxide-mediated oxidative stress. | 2005 Apr 1 |
|
| Altered expression of iron transport proteins in streptozotocin-induced diabetic rat kidney. | 2005 Apr 15 |
|
| Spirohydantoin derivatives of thiopyrano[2,3-b]pyridin-4(4H)-one as potent in vitro and in vivo aldose reductase inhibitors. | 2005 Jan 17 |
|
| [Effects of aldose reductase on the expression of fibronectin and collagen IV in cultured rat renal mesangial cells]. | 2005 Mar |
|
| Requirement of aldose reductase for the hyperglycemic activation of protein kinase C and formation of diacylglycerol in vascular smooth muscle cells. | 2005 Mar |
|
| Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options. | 2005 May |
|
| Contribution of aldose reductase to diabetic hyperproliferation of vascular smooth muscle cells. | 2006 Apr |
|
| Aldose reductase prevents aldehyde toxicity in cultured human lens epithelial cells. | 2006 Aug |
|
| Inhibition of aldose reductase prevents lipopolysaccharide-induced inflammatory response in human lens epithelial cells. | 2006 Dec |
|
| Mediation of aldose reductase in lipopolysaccharide-induced inflammatory signals in mouse peritoneal macrophages. | 2006 Nov |
|
| The polyol pathway as a mechanism for diabetic retinopathy: attractive, elusive, and resilient. | 2007 |
|
| Current concepts in targeted therapies for the pathophysiology of diabetic microvascular complications. | 2007 |
|
| Evidence for a novel binding site conformer of aldose reductase in ligand-bound state. | 2007 May 25 |
|
| Tracing changes in protonation: a prerequisite to factorize thermodynamic data of inhibitor binding to aldose reductase. | 2007 Nov 9 |
|
| Aldose reductase inhibitors for the treatment of diabetic polyneuropathy. | 2007 Oct 17 |
|
| Aldose reductase-regulated tumor necrosis factor-alpha production is essential for high glucose-induced vascular smooth muscle cell growth. | 2007 Sep |
|
| Role of nitric oxide in regulating aldose reductase activation in the ischemic heart. | 2008 Apr 4 |
|
| Endotoxin causes pulmonary hypertension by upregulating smooth muscle endothelin type-B receptors: role of aldose reductase. | 2008 Aug |
|
| Treatment of diabetic neuropathy and neuropathic pain: how far have we come? | 2008 Feb |
|
| The effect of hydrogen peroxide on sarco/endoplasmic and plasma membrane calcium ATPase gene expression in cultured human lens epithelial cells. | 2008 Jul 7 |
|
| Current and future approaches in the prevention and treatment of diabetic retinopathy. | 2008 Jun |
|
| Inhibition of aldose reductase prevents experimental allergic airway inflammation in mice. | 2009 Aug 6 |
|
| Aldose reductase regulates high glucose-induced ectodomain shedding of tumor necrosis factor (TNF)-alpha via protein kinase C-delta and TNF-alpha converting enzyme in vascular smooth muscle cells. | 2009 Jan |
|
| Advances in pharmacological strategies for the prevention of cataract development. | 2009 May-Jun |
|
| Aldose reductase protects against early atherosclerotic lesion formation in apolipoprotein E-null mice. | 2009 Oct 9 |
|
| Oxidative stress and dysregulation of the taurine transporter in high-glucose-exposed human Schwann cells: implications for pathogenesis of diabetic neuropathy. | 2009 Sep |
|
| Role of aldose reductase in the high glucose induced expression of fibronectin in human mesangial cells. | 2010 Jul |
|
| Aldose reductase regulates vascular smooth muscle cell proliferation by modulating G1/S phase transition of cell cycle. | 2010 May |
Sample Use Guides
Microsome-generated metabolites of sorbinil (50 microM) were toxic to normal peripheral blood lymphocytes (7.9% +/- 0.3% dead cells [mean +/- SE]). Toxicity was increased in the presence of an epoxide hydrolase inhibitor and abolished by an inhibitor of cytochrome P-450. In contrast to cells from healthy controls and diabetics who tolerated sorbinil, cells from the six patients who had sorbinil reactions showed significantly increased toxicity from metabolites of sorbinil and phenytoin. It was concluded that sorbinil is oxidatively metabolized to a potentially toxic intermediate.
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NCI_THESAURUS |
C72880
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C97357
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68367-52-2
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CHEMBL266497
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Sorbinil
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ACTIVE MOIETY
