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Identification
NameSorbinil
Accession NumberDB02712  (EXPT03309)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SorbinilNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIG4186B906P
CAS number68367-52-2
WeightAverage: 236.1992
Monoisotopic: 236.059720369
Chemical FormulaC11H9FN2O3
InChI KeyInChIKey=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[C@]3(NC(=O)NC3=O)C2=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 5-monosubstituted hydantoin
  • Ureide
  • Fluorobenzene
  • Alkyl aryl ether
  • Benzenoid
  • Aryl halide
  • Aryl fluoride
  • Urea
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.63 mg/mLALOGPS
logP0.59ALOGPS
logP0.44ChemAxon
logS-1.9ALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18