ChemicalBook > CAS DataBase List > Diltiazem hydrochloride

Diltiazem hydrochloride

Product Name
Diltiazem hydrochloride
CAS No.
33286-22-5
Chemical Name
Diltiazem hydrochloride
Synonyms
DILTIAZEM HCL;DILTHIAZEM HYDROCHLORIDE;Tiazac;Sprix;Acuvail;cardizem;herbesser;Dilacor XR;Diltiazem Hydrochlorid;(2S,cis)-3-(Acetyloxy)-5-[(2-dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one Hydrochloride
CBNumber
CB7302994
Molecular Formula
C22H27ClN2O4S
Formula Weight
450.98
MOL File
33286-22-5.mol
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Diltiazem hydrochloride Property

Melting point:
212-214 °C
alpha 
D24 +98.3 ± 1.4° (c = 1.002 in methanol)
Density 
1.30 g/cm3
refractive index 
118 ° (C=1, H2O)
Flash point:
2℃
storage temp. 
2-8°C
solubility 
Freely soluble in water, in methanol and in methylene chloride, slightly soluble in anhydrous ethanol.
form 
Powder
color 
White to off-white
PH
pH (10g/l, 25℃) : 4.3～5.3
Water Solubility 
soluble
Merck 
13,3226
BRN 
4228706
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
CAS DataBase Reference
33286-22-5(CAS DataBase Reference)
EPA Substance Registry System
1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, hydrochloride (1:1), (2S,3S)- (33286-22-5)
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Safety

Hazard Codes 
Xn,Xi,F
Risk Statements 
22-40-36/37/38-36-20/21/22-11
Safety Statements 
36-45-36/37-26-16
RIDADR 
3249
WGK Germany 
3
RTECS 
DL0310000
F 
8-10
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29349990
Toxicity
LD50 in male, female mice, male, female rats (mg/kg): 61, 58, 38, 39 i.v.; 260, 280, 520, 550 s.c.; 740, 640, 560, 610 orally (Nagao, 1972)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2856
Product name
Diltiazem Hydrochloride
Purity
certified reference material, pharmaceutical secondary standard
Packaging
500MG
Price
$218
Updated
2024/03/01
Sigma-Aldrich
Product number
D-035
Product name
Diltiazem hydrochloride solution
Purity
1.0?mg/mL in acetonitrile (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$69
Updated
2024/03/01
Sigma-Aldrich
Product number
309866
Product name
Diltiazem, Hydrochloride
Purity
Synthetic benzothiazepine that acts as an L-type Ca
Packaging
100mg
Price
$96.7
Updated
2024/03/01
Sigma-Aldrich
Product number
1205003
Product name
Diltiazem hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP899
Product name
Diltiazem impurity standard
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$227
Updated
2023/01/07
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Diltiazem hydrochloride Chemical Properties,Usage,Production

Description

Diltiazem HCl (33286-22-5) is a?non-dihydropyridine-type blocker of L-type Ca2+ channels.1,2 Reduces Ca2+ oscillations in subcellular compartments in vascular smooth muscle cells.3?Also blocks P-type Ca2+ channels in freshly dissociated rat cerebellar Purkinje neurons.4 Clinically useful antihypertensive agent.5?Cell permeable.

Chemical Properties

Diltiazem hydrochloride is a white to off-white crystalline powder with a bitter taste. It is soluble in water, methanol, and chloroform. It has a molecular weight of 450.98. Diltiazem hydrochloride injection is a clear, colorless, sterile, nonpyrogenic solution. It has a pH range of 3.7 to 4.1.

Originator

Herbesser,TANABE SEIYAKU,Japan,1974

Uses

Diltiazem Hydrochloride is a calcium channel blocker with vasodilating activity. Anti-anginal; anti-hypertensive; anti-arrhythmic (class IV).

Uses

antihypertensive, sedative, antibacterial

Uses

Peripheral Vasodilator

Uses

An antianginal, antihypertensive. Regulates Calcium release from intracellular stores in neutrophils

Definition

ChEBI: Diltiazem hydrochloride is a hydrochloride salt resulting from the reaction of equimolar amounts of diltiazem and hydrogen chloride. A calcium-channel blocker and vasodilator, it is used in the management of angina pectoris and hypertension. It has a role as an antihypertensive agent, a vasodilator agent and a calcium channel blocker. It contains a diltiazem(1+). It is an enantiomer of an ent-diltiazem hydrochloride.

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.

brand name

Cardizem (Biovail); Cartia (Andrx); Dilacor (Watson); Diltzac (Apotex); Taztia (Andrx); Tiazac (Biovail).

Therapeutic Function

Coronary vasodilator

General Description

Diltiazem hydrochloride is a calcium ion cellular influx inhibitor. It was developed and introduced inJapan as a cardiovascular agent to treat angina pectoris. Itwas observed to dilate peripheral arteries and arterioles. Thedrug increases myocardial oxygen supply by relieving coronaryartery spasm and reduces myocardial oxygen demandby decreasing heart rate and reducing overload. Diltiazemhydrochloride is used in patients with variant angina. Thedrug has electrophysiological properties similar to those ofverapamil and is used in clinically similar treatment conditionsas an antiarrhythmic agent, but it is less potent.
The drug is absorbed rapidly and almost completely fromthe digestive tract. It reaches peak plasma levels within 1hour after administration in gelatin capsules. Oral formulationson the market are sustained-release preparations providingpeak plasma levels 3 to 4 hours after administration.

Biological Activity

Antihypertensive and cardioprotective agent; an inhibitor of L-type Ca 2+ channels.

Biochem/physiol Actions

Product does not compete with ATP.

Clinical Use

Calcium-channel blocker:
Prophylaxis and treatment of angina
Hypertension

Metabolism

Diltiazem is almost completely absorbed from the gastrointestinal tract after oral doses, but undergoes extensive first-pass hepatic metabolism resulting in a bioavailability of about 40%. It is extensively metabolised in the liver, mainly by the cytochrome P450 isoenzyme CYP3A4; one of the metabolites, desacetyldiltiazem, has been reported to have 25-50% of the activity of the parent compound
About 2-4% of a dose is excreted in urine as unchanged diltiazem with the remainder excreted as metabolites in bile and urine.

storage

Store at RT

Mode of action

Diltiazem Hydrochloride is a benzothiazepine calcium channel blocking agent. Diltiazem hydrochloride inhibits the transmembrane influx of extracellular calcium ions into select myocardial and vascular smooth muscle cells, causing dilatation of coronary and systemic arteries and decreasing myocardial contractility. Because of its vasodilatory activity, this agent has been shown to improve the microcirculation in some tumors, thereby potentially improving the delivery of antineoplastic agents to tumor cells.

References

1) Kraus?et al.?(1998),?Molecular mechanism of diltiazem interaction with L-type Ca2+ channels; J. Biol. Chem.,?273?27205 2) Godfraind?et al. (1986),?Calcium antagonism and calcium entry blockade; Pharmacol. Rev.,?38?321 3) Fedoryak?et al.?(2004),?Spontaneous Ca2+ oscillations in subcellular compartments of vascular smooth muscle cells rely on different Ca2+ pools; Cell Res.,?14?379 4) Ishibashi?et al. (1995),?Block of P-type Ca2+ channels in freshly dissociated rat cerebellar Purkinje neurons by diltiazem and verapamil; Brain Res.,?695?88 5) Chaffman and Bogden (1985),?Diltiazem. A review of its pharmacological properties and therapeutic efficacy; Drugs,?29?387

Diltiazem hydrochloride Preparation Products And Raw materials

Raw materials

Ethyl propionate 2-Chloroethyldimethylamine Aza 2-Aminobenzenethiol

Preparation Products

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View Lastest Price from Diltiazem hydrochloride manufacturers

Hebei Miaoyin Technology Co.,Ltd
Product
diltiazem hydrochloride 33286-22-5
Price
US $20.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000
Release date
2023-04-13
Baoji Guokang Bio-Technology Co., Ltd.
Product
Dilthiazem hydrochloride 33286-22-5
Price
US $510.00/Kg/Bag
Min. Order
1KG
Purity
98%
Supply Ability
1T
Release date
2021-06-04
Hebei Yanxi Chemical Co., Ltd.
Product
Diltiazem hydrochloride 33286-22-5
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100tons
Release date
2023-08-11

33286-22-5, Diltiazem hydrochlorideRelated Search:

Ethylparaben Ethyl cyanoacetate (Trifluoromethoxy)benzene Ethyl pyruvate 4-Methoxyphenylacetone ISOXADIFEN-ETHYL 1-AdaMantanethylaMine Methoxyacetic acid m-Anisyl alcohol p-Anisaldehyde Diltiazem Ethyl acrylate p-Anisidine Ethyl acetate 3-Dimethylaminopropylamine Ethyl formate Ethanol Anisole Diltiazem Hcl

  • (2S-cis)-3-acetoxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride
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  • Zilden
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  • CRD-401, (2S,3S)-(+)-cis-3-Acetoxy-5-(2-dimethylaminoethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride
  • (+)-cis-Diltiazem hydrochloride,(2S,3S)-(+)-cis-3-Acetoxy-5-(2-dimethylaminoethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride, CRD-401
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  • Diltiazem, Hydrochloride - CAS 33286-22-5 - Calbiochem