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

• ChemBase ID: 165450
• Molecular Formular: C19H23ClN2O3S
• Molecular Mass: 394.91552
• Monoisotopic Mass: 394.11179129
• SMILES: c1(ccc(cc1)C1[C@H](C(=O)N(c2c(S1)cccc2)CCN(C)C)O)O.Cl
• Canonical SMILES: CN(CCN1c2ccccc2SC([C@H](C1=O)O)c1ccc(cc1)O)C.Cl
• InChI: InChI=1S/C19H22N2O3S.ClH/c1-20(2)11-12-21-15-5-3-4-6-16(15)25-18(17(23)19(21)24)13-7-9-14(22)10-8-13;/h3-10,17-18,22-23H,11-12H2,1-2H3;1H/t17-,18?;/m1./s1
• InChIKey: NPMHEOKYIXUNBP-XRVQSCEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one hydrochloride
• IUPAC Traditional name: (3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-one hydrochloride
• Synonyms: Deacetyl-O-demethyldiltiazem Hydrochloride; Deacetyl-O-demethyl Diltiazem Hydrochloride; (2S,3S)-5-[2-(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-hydroxyphenyl)-1,5-benzothiazepin-4(5H)-one Hydrochloride; Deacetyl-O-demethyl-d-diltiazem Hydrochloride

Database IDs

• CAS Number: 96252-32-3
• PubChem SID: 162259583
• PubChem CID: 71315208

CALCULATED PROPERTIES

• Acid pKa: 9.508102
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.47494596
• LogD (pH = 7.4): 1.2956442
• Log P: 1.9588261
• Molar Refractivity: 100.7325 cm^3
• Polarizability: 39.074585 Å^3
• Polar Surface Area: 64.01 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D198930

Diltiazem (D460620) metabolite.

REFERENCES

• Gendron, F., et al.: Biochem. Pharmacol., 60, 1959 (2000)
• Molden, E., et al.: J. Pharm. Biomed. Anal., 33, 275 (2000)
• Ma, J., et al.: Mol. Pharmacol., 72, 380 (2000)