(4S)-6-fluoro-2,3-dihydrospiro[1-benzopyran-4,4'-imidazolidine]-2',5'-dione

• ChemBase ID: 2434
• Molecular Formular: C11H9FN2O3
• Molecular Mass: 236.1991632
• Monoisotopic Mass: 236.05972038
• SMILES: c1(F)ccc2OCC[C@@]3(C(=O)NC(=O)N3)c2c1
• Canonical SMILES: Fc1cc2[C@]3(CCOc2cc1)NC(=O)NC3=O
• 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
• InChIKey: LXANPKRCLVQAOG-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-6-fluoro-2,3-dihydrospiro[1-benzopyran-4,4'-imidazolidine]-2',5'-dione
• IUPAC Traditional name: sorbinil; @sorbinil
• Brand Name: Sorbinil
• Synonyms: (+)-(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; Sorbinil; Sorbinil

Database IDs

• CAS Number: 68367-52-2
• MDL Number: MFCD00867380
• PubChem SID: 46504981; 160965885
• PubChem CID: 337359

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.147243
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.4355356
• LogD (pH = 7.4): 0.42801753
• Log P: 0.43563235
• Molar Refractivity: 54.9447 cm^3
• Polarizability: 21.004667 Å^3
• Polar Surface Area: 67.43 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.59
• LOG S: -1.95
• Solubility (Water): 2.63e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder
• Optical Rotation: [α]/D +50 to +60°, c = 1 in methanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H9FN2O3

DETAILS

DrugBank - DB02712

Drug information: experimental

Sigma Aldrich - S7701

Biochem/physiol Actions
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.