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

• ChemBase编号: 227
• 分子式: C22H26N2O4S
• 平均质量: 414.51784
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
• IUPAC传统名: diltiazem
• 商标名: 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
• 别名: d-cis-Diltiazem; Diltiazem

登记号

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

理论计算性质

JChem

• Acid pKa: 12.860752
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.111457996
• LogD (pH = 7.4): 1.885419
• Log P: 2.7272518
• 摩尔折射率: 114.3663 cm^3
• 极化性: 44.8192 Å^3
• 极化表面积: 59.08 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.09
• LOG S: -4.39
• 溶解度: 1.68e-02 g/l

分子性质

理化性质

• 溶解度: 465 mg/L
• 疏水性(logP): 2.8

详细说明

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