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

• ChemBase ID: 166431
• Molecular Formular: C21H25ClN2O4S
• Molecular Mass: 436.9522
• Monoisotopic Mass: 436.12235597
• SMILES: c1(ccc(cc1)[C@H]1[C@H](C(=O)N(c2c(S1)cccc2)CCNC)OC(=O)C)OC.Cl
• Canonical SMILES: CNCCN1C(=O)[C@H](OC(=O)C)[C@@H](Sc2c1cccc2)c1ccc(cc1)OC.Cl
• InChI: InChI=1S/C21H24N2O4S.ClH/c1-14(24)27-19-20(15-8-10-16(26-3)11-9-15)28-18-7-5-4-6-17(18)23(21(19)25)13-12-22-2;/h4-11,19-20,22H,12-13H2,1-3H3;1H/t19-,20+;/m1./s1
• InChIKey: GIYQYIVUHPJUHS-FDOHDBATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride
• IUPAC Traditional name: (2S,3S)-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl acetate hydrochloride
• Synonyms: (2S-cis)-3-(Acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]-1,5-benzothiazepin-4(5H)-one Monohydrochloride; N-Demethyldiltiazem; N-Monodesmethyldiltiazem; N-Desmethyl Diltiazem Hydrochloride

Database IDs

• CAS Number: 130606-60-9
• PubChem SID: 162260564
• PubChem CID: 14391644

CALCULATED PROPERTIES

• Acid pKa: 12.86089
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7676026
• LogD (pH = 7.4): 0.55461824
• Log P: 2.344204
• Molar Refractivity: 109.0716 cm^3
• Polarizability: 42.97921 Å^3
• Polar Surface Area: 67.87 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 186-189°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D291610

A metabolite of Diltiazem (D460620), an antianginal, antihypertensive pharmaceutical. Diltiazem regulates Calcium release from intracellular stores in neutrophils.

REFERENCES

• Li, R., et al.: J. Med. Chem., 35, 3246 (1992)