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

• ChemBase ID: 72812
• Molecular Formular: C22H27ClN2O4S
• Molecular Mass: 450.97878
• Monoisotopic Mass: 450.13800603
• SMILES: c12N(C(=O)[C@@H]([C@@H](Sc1cccc2)c1ccc(cc1)OC)OC(=O)C)CCN(C)C.Cl
• Canonical SMILES: COc1ccc(cc1)[C@@H]1Sc2ccccc2N(C(=O)[C@@H]1OC(=O)C)CCN(C)C.Cl
• InChI: InChI=1S/C22H26N2O4S.ClH/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3;/h5-12,20-21H,13-14H2,1-4H3;1H/t20-,21+;/m1./s1
• InChIKey: HDRXZJPWHTXQRI-BHDTVMLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride
• IUPAC Traditional name: diltiazem hydrochloride
• Synonyms: (2S,3S)-(+)-cis-3-Acetoxy-5-(2-dimethylaminoethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride; CRD-401; (+)-cis-Diltiazem hydrochloride; Tiazac; Cardizem; Diltiazem HCl; (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride

Database IDs

• CAS Number: 33286-22-5
• EC Number: 251-443-3
• MDL Number: MFCD00069252
• Beilstein Number: 4228706
• PubChem SID: 24277849; 162037733
• PubChem CID: 62920

CALCULATED PROPERTIES

• Acid pKa: 12.860752
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.111457996
• LogD (pH = 7.4): 1.885419
• Log P: 2.7272518
• Molar Refractivity: 114.3663 cm^3
• Polarizability: 44.8192 Å^3
• Polar Surface Area: 59.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 212-214 °C
• Optical Rotation: [α]20/D +116±2°, c = 1% in H2O
• Hydrophobicity(logP): 3.647

Safety Information

• Storage Condition: -20°C
• RTECS: DL0310000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC); ≥99.0% (HPLC); 95%
• Salt Data: HCL; HCl
• Empirical Formula (Hill Notation): C22H26N2O4S · HCl
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Selleck Chemicals - S1865

Research Area: Cardiovascular Disease
Biological Activity:
Diltiazem HCl (Tiazac)  is a benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, dilitiazem, like verapamil, inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue. [1]

Sigma Aldrich - D2521

Biochem/physiol Actions
Blocks slow, or L-type Ca2+ channels; regulates Ca2+ release from intracellular stores in neutrophils; stimulates 1,4-dihydropyridine binding to Ca2+ channels; coronary vasodilator.

Sigma Aldrich - 38489

Other Notes
Pharmacology of calcium antagonists, review1

REFERENCES

• www.bentham.org/prc/samples/prc1-1/Higashi.pdf