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S7701

Sigma-Aldrich

Sorbinil

≥98% (HPLC)

Synonym(s):

(+)-(4S)-6-Fluorospiro[chroman-4,4′-imidazolidine]-2′,5′-dione, (4S)-6-Fluoro-2,3-dihydro-spiro[4H-1-benzopyran-4,4′-imidazolidine]-2′,5′-dione, CP 45634

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About This Item

Empirical Formula (Hill Notation):
C11H9FN2O3
CAS Number:
68367-52-2
Molecular Weight:
236.20
MDL number:
MFCD00867380
UNSPSC Code:
12352200
PubChem Substance ID:
329824587
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +50 to +60°, c = 1 in methanol

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Fc1ccc2OCC[C@]3(NC(=O)NC3=O)c2c1

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

InChI key

LXANPKRCLVQAOG-NSHDSACASA-N

Application

Sorbinil has been used as an aldose reductase inhibitor in diabetic rats as a positive control group.
Sorbinil may be used in cell signaling and neuroscience studies.

Biochem/physiol Actions

Sorbinil decreases the level of sorbitol in red blood cells and increases the velocity of nerve conduction. It maintains the myo-inositol content in the nerve and prevents the reduction of sodium-potassium ATPase activity. This action is beneficial in providing symptomatic relief in patients with diabetic neuropathy.
Sorbinil is an inhibitor of Aldose Reductase (AR). AR family members AKR1B1 and AKR1B10 have additionally been shown to play roles in inflammation and cancer.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Disclaimer

RESEARCH USE ONLY. This product is regulated in France when intended to be used for scientific purposes, including for import and export activities (Article L 1211-1 paragraph 2 of the Public Health Code). The purchaser (i.e. enduser) is required to obtain an import authorization from the France Ministry of Research referred in the Article L1245-5-1 II. of Public Health Code. By ordering this product, you are confirming that you have obtained the proper import authorization.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Antonella Del-Corso et al.
PloS one, 8(9), e74076-e74076 (2013-09-11)
Aldose reductase (AR) is an NADPH-dependent reductase, which acts on a variety of hydrophilic as well as hydrophobic aldehydes. It is currently defined as the first enzyme in the so-called polyol pathway, in which glucose is transformed into sorbitol by
Sonia Manzanaro et al.
Journal of natural products, 69(10), 1485-1487 (2006-10-28)
Four different types of marine natural compounds isolated from tunicates were found to inhibit human aldose reductase. They all are characterized by a heterocyclic system, and at least two phenolic groups are present in the structure. Two of the compounds
Eleonora Peroni et al.
Antioxidants (Basel, Switzerland), 9(5) (2020-05-10)
One of the consequences of the increased level of oxidative stress that often characterizes the cancer cell environment is the abnormal generation of lipid peroxidation products, above all 4-hydroxynonenal. The contribution of this aldehyde to the pathogenesis of several diseases
Sally A Madsen-Bouterse et al.
Reviews in endocrine & metabolic disorders, 9(4), 315-327 (2008-07-26)
Retinopathy is one of the most severe ocular complications of diabetes and is a leading cause of acquired blindness in young adults. The cellular components of the retina are highly coordinated but very susceptible to the hyperglycemic environment. The microvasculature
R J Young et al.
Diabetes, 32(10), 938-942 (1983-10-01)
A double-blind, randomized, placebo-controlled cross-over trial of the aldose reductase inhibitor sorbinil was undertaken in 15 patients (age 35-68 yr) with chronic painful diabetic neuropathy. Treatment was evaluated by subjective pain responses, clinical examination, vibration perception threshold, motor and sensory
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