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

• ChemBase ID: 227
• Molecular Formular: C22H26N2O4S
• Molecular Mass: 414.51784
• Monoisotopic Mass: 414.16132832
• SMILES: S1[C@H]([C@@H](OC(=O)C)C(=O)N(CCN(C)C)c2c1cccc2)c1ccc(OC)cc1
• Canonical SMILES: COc1ccc(cc1)[C@@H]1Sc2ccccc2N(C(=O)[C@@H]1OC(=O)C)CCN(C)C
• InChI: InChI=1S/C22H26N2O4S/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/t20-,21+/m1/s1
• InChIKey: HSUGRBWQSSZJOP-RTWAWAEBSA-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
• IUPAC Traditional name: diltiazem
• Brand Name: Acalix; Adizem; Altiazem; Anginyl; Angizem; Anoheal; Apo-Diltiaz; Britiazim; Bruzem; Calcicard; Cardizem; Cardizem CD; Cardizem SR; Cardizen LA; Cartia XT; Citizem; Cormax; Deltazen; Dilacor; Dilacor-XR; Diladel; Dilcontin; Dilpral; Dilrene; Dilt-cd; Dilta-Hexal; Diltia; Dilticard; Dilzem; Dilzen; Endrydil; Herbesser; Incoril AP; Masdil; Novo-Diltazem; Nu-Diltiaz; Syn-Diltiazem; Tiazac Tildiem; Tiazac; Tiazac XC; Tiamate; Viazem
• Synonyms: d-cis-Diltiazem; Diltiazem

Database IDs

• CAS Number: 42399-41-7
• PubChem SID: 46505667; 160963690
• PubChem CID: 39186

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.09
• LOG S: -4.39
• Solubility (Water): 1.68e-02 g/l

PROPERTIES

Physical Property

• Solubility: 465 mg/L
• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB00343

• Drug Groups: approved
• Description: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem]
• Indication: For the treatment of Hypertension
• Pharmacology: Diltiazem, a benzothiazepine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Diltiazem is a non-dihydropyridine (DHP)member of the calcium channel blocker class, along with Verapamil. Diltiazem is similar to other peripheral vasodilators. Diltiazem inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
• Toxicity: LD₅₀=740mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Diltiazem is metabolized by and acts as an inhibitor of the CYP3A4 enzyme.
• Absorption: Diltiazem is well absorbed from the gastrointestinal tract but undergoes substantial hepatic first-pass effect.
• Half Life: 3.0 - 4.5 hours
• Protein Binding: 70%-80%
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com