(2S,3S)-5-[2-amino(2H4)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride

• ChemBase ID: 167238
• Molecular Formular: C20H23ClN2O4S
• Molecular Mass: 422.92562
• Monoisotopic Mass: 422.10670591
• SMILES: N1(C(=O)[C@@H]([C@@H](Sc2c1cccc2)c1ccc(cc1)OC)OC(=O)C)CCN.Cl
• Canonical SMILES: NCCN1C(=O)[C@H](OC(=O)C)[C@@H](Sc2c1cccc2)c1ccc(cc1)OC.Cl
• InChI: InChI=1S/C20H22N2O4S.ClH/c1-13(23)26-18-19(14-7-9-15(25-2)10-8-14)27-17-6-4-3-5-16(17)22(12-11-21)20(18)24;/h3-10,18-19H,11-12,21H2,1-2H3;1H/t18-,19+;/m1./s1
• InChIKey: AFGVHOBXBDWFNW-VOMIJIAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-5-[2-amino(^2H₄)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride
• IUPAC Traditional name: (2S,3S)-5-[2-amino(^2H₄)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl acetate hydrochloride
• Synonyms: (2S-cis)-3-(Acetyloxy)-5-(2-aminoethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one-d4 Monohydrochloride; (2S,3S)-N,N-Didemethyldiltiazem-d4 Hydrochloride; N,N-Didesmethyl Diltiazem-d4 Hydrochloride

Database IDs

• PubChem SID: 162261371
• PubChem CID: 71316027

CALCULATED PROPERTIES

• Acid pKa: 12.860892
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.99230176
• LogD (pH = 7.4): 0.3232273
• Log P: 1.9116236
• Molar Refractivity: 104.297 cm^3
• Polarizability: 41.14034 Å^3
• Polar Surface Area: 81.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D441052

A labelled metabolite of Diltiazem (D460620).

REFERENCES

• Sutton, D., et al.: J. Pharmacol. Exp. Ther., 282, 294 (1997)
• Molden, E., et al.: J. Pharm. Biomed. Anal., 33, 275 (1997)