Identification

Name
Fidarestat
Accession Number
DB02021  (EXPT01433)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (S,S)-fidarestat
  • Aldos
Categories
UNII
8SH8T1164U
CAS number
136087-85-9
Weight
Average: 279.2239
Monoisotopic: 279.065534028
Chemical Formula
C12H10FN3O4
InChI Key
WAAPEIZFCHNLKK-UFBFGSQYSA-N
InChI
InChI=1S/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12-/m0/s1
IUPAC Name
(2S,4S)-6-fluoro-2',5'-dihydroxy-2,3-dihydrospiro[1-benzopyran-4,4'-imidazole]-2-carboximidic acid
SMILES
[H][[email protected]]1(C[[email protected]]2(N=C(O)N=C2O)C2=C(O1)C=CC(F)=C2)C(O)=N

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductase
inhibitor
Human
UAldo-keto reductase family 1 member B10
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

General References
Not Available
External Links
PubChem Compound
160024
PubChem Substance
46505893
ChemSpider
140679
BindingDB
16512
ChEMBL
CHEMBL84446
Therapeutic Targets Database
DCL000311
HET
FID
PDB Entries
1ef3 / 1pwm / 2agt / 2pd9 / 2pdw / 2pdy / 2pev / 2pf8 / 2pfh / 3h4g
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0698 mg/mLALOGPS
logP-0.01ALOGPS
logP-1.3ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)11.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.49 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.58 m3·mol-1ChemAxon
Polarizability24.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9598
Blood Brain Barrier+0.8433
Caco-2 permeable-0.6514
P-glycoprotein substrateSubstrate0.7662
P-glycoprotein inhibitor INon-inhibitor0.9093
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9168
CYP450 2C9 substrateNon-substrate0.8767
CYP450 2D6 substrateNon-substrate0.7907
CYP450 3A4 substrateNon-substrate0.5459
CYP450 1A2 substrateNon-inhibitor0.715
CYP450 2C9 inhibitorNon-inhibitor0.7759
CYP450 2D6 inhibitorNon-inhibitor0.8434
CYP450 2C19 inhibitorNon-inhibitor0.6696
CYP450 3A4 inhibitorNon-inhibitor0.9477
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9025
Ames testNon AMES toxic0.6861
CarcinogenicityNon-carcinogens0.8906
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.1766 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9916
hERG inhibition (predictor II)Non-inhibitor0.8959
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 / Primary carboxylic acid amides / Azacyclic compounds
show 7 more
Substituents
Hydantoin / Alpha-amino acid or derivatives / Chromane / Benzopyran / 1-benzopyran / 5-monosubstituted hydantoin / Alkyl aryl ether / Ureide / N-acyl urea / Aryl fluoride
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Retinal dehydrogenase activity
Specific Function
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldeh...
Gene Name
AKR1B10
Uniprot ID
O60218
Uniprot Name
Aldo-keto reductase family 1 member B10
Molecular Weight
36019.295 Da
References
  1. Ruiz FX, Cousido-Siah A, Mitschler A, Farres J, Pares X, Podjarny A: X-ray structure of the V301L aldo-keto reductase 1B10 complexed with NADP(+) and the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. Chem Biol Interact. 2013 Feb 25;202(1-3):178-85. doi: 10.1016/j.cbi.2012.12.013. Epub 2013 Jan 4. [PubMed:23295227]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:52