Identification

Name
Sorbinil
Accession Number
DB02712  (EXPT03309)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
CP-45,634 / CP-45634
International/Other Brands
Sorbinil
Categories
UNII
G4186B906P
CAS number
68367-52-2
Weight
Average: 236.1992
Monoisotopic: 236.059720369
Chemical Formula
C11H9FN2O3
InChI Key
LXANPKRCLVQAOG-NSHDSACASA-N
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
IUPAC Name
(4S)-6-fluoro-2,3-dihydrospiro[1-benzopyran-4,4'-imidazolidine]-2',5'-dione
SMILES
FC1=CC=C2OCC[[email protected]]3(NC(=O)NC3=O)C2=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductase
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Berkeley W. Cue, Jr., Philip D. Hammen, Stephen S. Massett, "Regeneration of 6-fluoro-4-chromanone from by-products in the synthesis of sorbinil." U.S. Patent US4431828, issued August, 1981.

US4431828
General References
Not Available
External Links
PubChem Compound
337359
PubChem Substance
46504981
ChemSpider
298991
BindingDB
16312
ChEBI
102029
ChEMBL
CHEMBL266497
Therapeutic Targets Database
DCL000270
HET
SBI
PDB Entries
1ah0 / 2pdk / 4ga8

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDiabetes Mellitus (DM) / Retinopathy, Diabetic1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.63 mg/mLALOGPS
logP0.59ALOGPS
logP0.44ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.43 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.94 m3·mol-1ChemAxon
Polarizability20.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9841
Blood Brain Barrier+0.8909
Caco-2 permeable-0.6021
P-glycoprotein substrateSubstrate0.765
P-glycoprotein inhibitor INon-inhibitor0.8602
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8326
CYP450 2D6 substrateNon-substrate0.7526
CYP450 3A4 substrateNon-substrate0.5179
CYP450 1A2 substrateNon-inhibitor0.6004
CYP450 2C9 inhibitorNon-inhibitor0.6738
CYP450 2D6 inhibitorNon-inhibitor0.8405
CYP450 2C19 inhibitorNon-inhibitor0.5509
CYP450 3A4 inhibitorNon-inhibitor0.9654
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8779
Ames testNon AMES toxic0.6783
CarcinogenicityNon-carcinogens0.9121
BiodegradationNot ready biodegradable0.9854
Rat acute toxicity2.3697 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9473
hERG inhibition (predictor II)Non-inhibitor0.7417
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azolidines
Sub Class
Imidazolidines
Direct Parent
Hydantoins
Alternative Parents
1-benzopyrans / Alpha amino acids and derivatives / 5-monosubstituted hydantoins / Alkyl aryl ethers / N-acyl ureas / Aryl fluorides / Benzenoids / Dicarboximides / Azacyclic compounds / Oxacyclic compounds
show 6 more
Substituents
Hydantoin / Alpha-amino acid or derivatives / Chromane / 1-benzopyran / Benzopyran / 5-monosubstituted hydantoin / Alkyl aryl ether / N-acyl urea / Ureide / Aryl fluoride
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, imidazolidinone, azaspiro compound, chromanes, oxaspiro compound (CHEBI:102029)

Targets

Details
1. Aldose reductase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:01