Diltiazem

Product Name: Diltiazem
CAS No.: 42399-41-7
Chemical Name: Diltiazem
Synonyms: DILTIAZEN;Dilthiazem;(2S,3S)-5-(2-(diMethylaMino)ethyl)-2-(4-Methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate;Coras;NSC7324;NSC 7324;NSC-7324;DILTIAZEM;Adizem XL;d-Diltiazem
CBNumber: CB5715839
Molecular Formula: C22H26N2O4S
Formula Weight: 414.52
MOL File: 42399-41-7.mol

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Diltiazem Property

Melting point:: 212 °C (decomp)
Boiling point:: 594.4±50.0 °C(Predicted)
Density: 1.26±0.1 g/cm3(Predicted)
storage temp.: -20°C Freezer
solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: pKa 7.70 (Uncertain)
color: White to Off-White
CAS DataBase Reference: 42399-41-7(CAS DataBase Reference)
NIST Chemistry Reference: Diltiazem(42399-41-7)
EPA Substance Registry System: 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)- (42399-41-7)

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Safety

Hazardous Substances Data: 42399-41-7(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: D460628
Product name: Diltiazem
Packaging: 1g
Price: $110
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD44512
Product name: Diltiazem
Packaging: 250mg
Price: $125
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0005791
Product name: DILTIAZEM
Purity: 95.00%
Packaging: 1G
Price: $155.4
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD44512
Product name: Diltiazem
Packaging: 500mg
Price: $200
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD44512
Product name: Diltiazem
Packaging: 1g
Price: $300
Updated: 2021/12/16

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Diltiazem Chemical Properties,Usage,Production

Originator

Herbesser,TANABE SEIYAKU,Japan,1974

Uses

It is used for stable and nonstable angina pectoris (including after myocardial infarctions) as well as in arterial hypertension.

Uses

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.

Manufacturing Process

β-Diethylaminoethyl chloride is condensed with 2-(4-methoxyphenyl)-3- hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one in a first step. Then a mixture of 1.5 grams of 2-(4-methoxyphenyl)-3-hydroxy-5-(βdimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 20 ml of acetic anhydride was heated on a water bath for 5 hours. The reaction mixture was evaporated under reduced pressure to remove acetic anhydride and the concentrated product was poured into ice water. The resulting mixture was made alkaline with sodium bicarbonate and extracted with chloroform. The chloroform layer was dried and evaporated to remove the solvent. The residue was dissolved in acetone, and an ethanol solution containing hydrogen chloride was added thereto producing 1.53 grams of 2-(4-methoxyphenyl)3- acetoxy-5-(β-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride having a melting point from 187° to 188°C.
The starting material is made by reacting 4-methoxybenzaldehyde with ethyl chloroacetate; that product with sodium ethoxide; and that product with 2- aminothiophenol.

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 (+)-|á-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).

Diltiazem Preparation Products And Raw materials

Raw materials

Preparation Products

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Diltiazem Suppliers

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View Lastest Price from Diltiazem manufacturers

Hebei Mujin Biotechnology Co.,Ltd

Product: Diltiazem 42399-41-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-06-30

Hebei Mojin Biotechnology Co.,Ltd

Product: Diltiazem 42399-41-7
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2024-06-03

Hebei Weibang Biotechnology Co., Ltd

Product: Diltiazem 42399-41-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-31

42399-41-7, DiltiazemRelated Search:

(Trifluoromethoxy)benzene p-Anisidine ISOXADIFEN-ETHYL Ethyl formate Ethyl pyruvate Ethyl acetate Diltiazem hydrochloride 3-Dimethylaminopropylamine Anisole Ethyl cyanoacetate Ethyl acrylate Ethanol Ethylparaben 4-Methoxyphenylacetone Chlorodimethylphenylsilane Methoxydiethylborane N,N-Dimethyl-1,4-phenylenediamine Diltiazem

(+)-5-[2-(Dimethylamino)ethyl]-cis-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate (ester)

(2s-cis)-dro-2-(4-methoxyphenyl)

(2S,3S)-2,3-Dihydro-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-1,5-benzothiazepine-4(5H)-one acetate

(2R)-3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

[2R,(+)]-3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

3α-Acetyloxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

[(2S,3S)-5-(2-dimethylaminoethyl)-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate

[(2S,3S)-5-(2-dimethylaminoethyl)-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] ethanoate

acetic acid [(2S,3S)-5-(2-dimethylaminoethyl)-4-keto-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-3-yl] ester

Diltiazem (free base)

O-DesMethyl DiltiazeM, HydrobroMide (Cis - RaceMic)

(2S,3S)-5-(2-(diMethylaMino)ethyl)-2-(4-Methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate

1,5-benzothiazepin-4(5h)-one,3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihy

1,5-benzothiazepin-4(5h)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihy

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

d-cis-diltiazem

(+)-CIS-DILTIAZEM

DILTIAZEM

DILTIAZEN

(2S)-5-[2-(Dimethylamino)ethyl]-2α,3α-dihydro-3β-acetyloxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

[(3S,4S)-6-(2-dimethylaminoethyl)-3-(4-methoxyphenyl)-5-oxo-2-thia-6-azabicyclo[5.4.0]undeca-7,9,11-trien-4-yl] acetate

1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-2-(dimethylamino)ethyl-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)-

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

Adizem XL

Coras

d-Diltiazem

TILDIEM300LP

Diltiazem (base and/or unspecified salts)

3-amino-1,2,4-triazole-1-carboxylic acid ethyl ester

Dilthiazem

High purity diltiazem/diltiazem hydrochloride

high quality Diltiazem

Diltiazem HCl salt

Diltiazem USP/EP/BP

NSC 7324

NSC7324

NSC-7324

(2S-Cis)-3-(Acetyloxy)-5-[2-dimethylamino)ethyl]-2,3-dihydro-2-(4methoxy phenyl)- 1,5benzothiazepin-4(5H)-one D

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

Diltiazem fandachem

42399-41-7

43299-41-7

C22H26N2O4S

42399-41-7