Sorbinil
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Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Sorbinil
- DrugBank Accession Number
- DB02712
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 236.1992
Monoisotopic: 236.059720369 - Chemical Formula
- C11H9FN2O3
- Synonyms
- Sorbinil
- sorbinilo
- Sorbinilum
- External IDs
- CP-45,634
- CP-45634
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AAldo-keto reductase family 1 member B1 inhibitorHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-benzopyran / 5-monosubstituted hydantoin / Alkyl aryl ether / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Benzopyran show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, imidazolidinone, azaspiro compound, chromanes, oxaspiro compound (CHEBI:102029)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- G4186B906P
- CAS number
- 68367-52-2
- 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[C@]3(NC(=O)NC3=O)C2=C1
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
- ZINC
- ZINC000000002070
- Therapeutic Targets Database
- DCL000270
- PDBe Ligand
- SBI
- Wikipedia
- Sorbinil
- PDB Entries
- 1ah0 / 2pdk / 4ga8
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Diabetes Mellitus / Diabetic Retinopathy (DR) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0.78 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.63 mg/mL ALOGPS logP 0.59 ALOGPS logP 0.44 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 8.67 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 67.43 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 54.94 m3·mol-1 Chemaxon Polarizability 20.84 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9841 Blood Brain Barrier + 0.8909 Caco-2 permeable - 0.6021 P-glycoprotein substrate Substrate 0.765 P-glycoprotein inhibitor I Non-inhibitor 0.8602 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.8178 CYP450 2C9 substrate Non-substrate 0.8326 CYP450 2D6 substrate Non-substrate 0.7526 CYP450 3A4 substrate Non-substrate 0.5179 CYP450 1A2 substrate Non-inhibitor 0.6004 CYP450 2C9 inhibitor Non-inhibitor 0.6738 CYP450 2D6 inhibitor Non-inhibitor 0.8405 CYP450 2C19 inhibitor Non-inhibitor 0.5509 CYP450 3A4 inhibitor Non-inhibitor 0.9654 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8779 Ames test Non AMES toxic 0.6783 Carcinogenicity Non-carcinogens 0.9121 Biodegradation Not ready biodegradable 0.9854 Rat acute toxicity 2.3697 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9473 hERG inhibition (predictor II) Non-inhibitor 0.7417
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-849e07e32661be0de8a6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0290000000-767a7b8222cb3ed7b68c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014u-0930000000-112649831f470b080a46 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9210000000-f570e9b0fdb7b1cf6268 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01bc-3910000000-93cc807525ab60bc4b02 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-7910000000-3c5726c198a2e723fd21 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 149.59856 predictedDeepCCS 1.0 (2019) [M+H]+ 151.97401 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.04971 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAldo-keto reductase family 1 member B1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia (PubMed:1936586). Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal (PubMed:12732097, PubMed:19010934, PubMed:8343525). Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides (PubMed:17381426). Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls) (PubMed:21329684)
- Specific Function
- aldose reductase (NADPH) activity
- Gene Name
- AKR1B1
- Uniprot ID
- P15121
- Uniprot Name
- Aldo-keto reductase family 1 member B1
- Molecular Weight
- 35853.125 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22