(2S,3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one

• ChemBase ID: 166110
• Molecular Formular: C20H24N2O3S
• Molecular Mass: 372.48116
• Monoisotopic Mass: 372.15076364
• SMILES: c1(ccc(cc1)[C@H]1[C@H](C(=O)N(c2c(S1)cccc2)CCN(C)C)O)OC
• Canonical SMILES: COc1ccc(cc1)[C@@H]1Sc2ccccc2N(C(=O)[C@@H]1O)CCN(C)C
• InChI: InChI=1S/C20H24N2O3S/c1-21(2)12-13-22-16-6-4-5-7-17(16)26-19(18(23)20(22)24)14-8-10-15(25-3)11-9-14/h4-11,18-19,23H,12-13H2,1-3H3/t18-,19+/m1/s1
• InChIKey: NZHUXMZTSSZXSB-MOPGFXCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one
• IUPAC Traditional name: desacetyldiltiazem
• Synonyms: (2S-cis)-5-[(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one; Deacetyl-d-diltiazem; Deacetyldiltiazem; Desacetyl Diltiazem

Database IDs

• CAS Number: 42399-40-6
• PubChem SID: 162260243
• PubChem CID: 91638

CALCULATED PROPERTIES

• Acid pKa: 12.334566
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.3296792
• LogD (pH = 7.4): 1.4442786
• Log P: 2.2861264
• Molar Refractivity: 105.2148 cm^3
• Polarizability: 40.987915 Å^3
• Polar Surface Area: 53.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White to Pale Yellow Solid

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D288685

A metabolite of Diltiazem (D460620).

REFERENCES

• Shallcross, H., et al.: Br. Med. J., 295, 1236 (1987)
• Yeung, P.K.F., et al.: Drug Metab. Dispos., 18, 1055 (1987)
• Cashman, J.R., et al.: J. Med. Chem., 34,2049 (1987)