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42399-41-7 molecular structure
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(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 and InChIs

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

Cite this record

CBID:227 http://www.chembase.cn/molecule-227.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
42399-41-7
PubChem SID
46505667
160963690
PubChem CID
39186

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00343 external link
PubChem 39186 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.860752  H Acceptors
H Donor LogD (pH = 5.5) 0.111457996 
LogD (pH = 7.4) 1.885419  Log P 2.7272518 
Molar Refractivity 114.3663 cm3 Polarizability 44.8192 Å3
Polar Surface Area 59.08 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.09  LOG S -4.39 
Solubility (Water) 1.68e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
465 mg/L expand Show data source
Hydrophobicity(logP)
2.8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00343 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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