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42399-41-7

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  • 1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,(2S,3S)- 42399-41-7

    Cas No: 42399-41-7

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42399-41-7 Usage

Uses

Different sources of media describe the Uses of 42399-41-7 differently. You can refer to the following data:
1. It is used for stable and nonstable angina pectoris (including after myocardial infarctions) as well as in arterial hypertension.
2. Diltiazem is a potent vasodilator compound. Antihypertensive.

Definition

ChEBI: A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the m nagement of angina pectoris and hypertension.

Therapeutic Function

Coronary vasodilator

Mechanism of action

Diltiazem reduces the transmembrane influx of calcium ions into cells of cardiac muscle and smooth musculature of vessels. It causes dilation of coronary and peripheral vessels, increases coronary blood flow, and prevents development of coronary artery spasms. It lowers elevated arterial pressure and reduces tachycardia.

Clinical Use

The antiarrhythmic actions and uses of diltiazem are similar to those of verapamil. Diltiazem is effective in controlling the ventricular rate in patients with atrial flutter or atrial fibrillation.

Synthesis

Diltiazem, 5-[2-(diethylamino)ethyl]-cis-2,3-dihydro-3-hydroxy-2- (4-methoxy-phenyl)-1,5-benzothiazepin-4(5H)-one (19.3.10), is synthesized in the following manner. The condensation of 4-methoxybenzaldehyde with methylchoroacetate in the presence of sodium methoxide in Darzens reaction conditions gives methyl ester of 3- (4-methoxyphenyl)-glycidylic acid (19.3.5). Reacting it with 2-aminothiophenol with the opening of epoxide ring gives methyl ester of 2-hydroxy-3-(2'-aminophenylthio)-3- (4"- methoxyphenyl)propionic acid (19.3.6). Hydrolysis of the resulting compound with alkali leads to the formation of the corresponding acid (19.3.7) in the form of a racemic mixture, which when on interaction with (+)-α-phenylethylamine gives threo-(+)-2-hydroxy-3-(2'- aminophenylthio)-3-(4"-methoxyphenylpropionic acid (19.3.8). Boiling this in a mixture of acetic anhydride/dimethylformamide/pyridine system brings to cyclization to the thiazepine ring and simultaneously acylates the hydroxyl group, forming (+)-cis-2-(4-methoxyphenyl)- 3-acetoxy-2,3-dihydro-1,5-benzothiazepin-4-(5H)-one (19.3.9). Alkylation of the resulting product with 2,2-dimethylaminoethylchloride forms diltiazem (19.3.10).

Check Digit Verification of cas no

The CAS Registry Mumber 42399-41-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,3,9 and 9 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 42399-41:
(7*4)+(6*2)+(5*3)+(4*9)+(3*9)+(2*4)+(1*1)=127
127 % 10 = 7
So 42399-41-7 is a valid CAS Registry Number.
InChI:InChI=1/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

42399-41-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name diltiazem

1.2 Other means of identification

Product number -
Other names Coras

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:42399-41-7 SDS

42399-41-7Relevant articles and documents

Crystal structures and physicochemical properties of diltiazem base and its acetylsalicylate, nicotinate and l-malate salts

Stepanovs,Jure,Gosteva,Popelis,Kiselovs,Mishnev

, p. 1235 - 1241 (2016)

Diltiazem is a drug used as a calcium channel blocker in the treatment of cardiovascular disorders. Because of the poor aqueous solubility of the drug, its hydrochloride salt has been marketed. Due to the short elimination half-life of diltiazem, extended-release formulations were developed. In the present work, the crystal engineering approach has been employed to obtain diltiazem forms with lower water solubility by treating with carboxylic acids. Three molecular salts of diltiazem with aspirin, niacin and l-malic acid were synthesized and characterized by single crystal and powder XRD, DTA, solid state CP-MAS, NMR and UV/vis techniques. The single crystal structure determination allowed us to study the supramolecular structures and proton transfer interactions from the carboxylic acids to diltiazem in the solid state, while the NMR studies showed the interactions in solution. In the crystal, the N,N-(dimethyl)ethylamine fragment of the drug molecule interacts with the carboxylic groups of the acids to form heterosynthons. The maximum 40-fold decrease of the aqueous solubility is achieved for diltiazem acetylsalicylate hydrate in comparison with the solubility of diltiazem hydrochloride.

Studies of the Resolution of Racemates in the Synthesis of Diltiazem

Gizur, Tibor,Harsanyi, Kalman,Fogassy, Elemer

, p. 628 - 631 (1994)

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Methods for predicting the response to statins

-

, (2011/10/13)

The invention provides methods for optimizing therapeutic efficacy for treating hypercholesterolemia in a subject having a cardiovascular disease (CVD), comprising (a) determining subject characteristics that affect the likelihood of reaching a goal level of low density lipoprotein (LDL); and (b) obtaining success probabilities of a variety of statin treatments for reaching said goal level of LDL using said subject characteristics and a multivariate model; and (c) administrating the optimal statin treatment with the highest success probability of step (b) to said subject thereby optimizing therapeutic efficacy for treating hypercholesterolemia in said subject.

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