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Diltiazem hydrochloride

pharmaceutical raw materials
Diltiazem hydrochloride structure

Diltiazem hydrochloride 

structure
  • CAS No:

    33286-22-5

  • Formula:

    C22H26N2O4S.ClH

  • Chemical Name:

    Diltiazem hydrochloride

  • Synonyms:

    1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,hydrochloride (1:1),(2S,3S)-;1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride,(2S-cis)-;1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride,(2S,3S)-;CRD 401;d-cis-3-Acetoxy-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride;Diltiazem hydrochloride;Herbesser;Tildiem;Masdil;(+)-Diltiazem hydrochloride;Cardizem;Blocalcin 60;(S,S)-Diltiazem hydrochloride;Tiazac;Kardil;Cardizem CD;Cardizem SR;Dilacor XR;Dilacor;Bruzem;Anginyl;Diladel;Dilpral;Dilrene;RG 83606;Angizem;Deltazen;Adizem;d-cis-Diltiazem hydrochloride;Altiazem;Dilzene;Citizem;Calcicard;Cormax;Britiazim;Dilcardia;Dilgard;Kaizem;Angipress;Dicard;(2S,3S)-(+)-cis-Diltiazem hydrochloride;Bi-Teldiem;Dilzacard

  • Categories:

    Cosmetic Ingredient  >  Skin Protecting

Description

Diltiazem hydrochloride is a Ca2+ influx inhibitor (slow channel blocker or calcium antagonist).


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.|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. (NCI04)|A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.

Diltiazem hydrochloride Basic Attributes

450.98

450.138000

251-443-3

OLH94387TE

DTXSID8040147

C398

2934999090

Characteristics

84.4

4.23550

White to off-white Powder

1.30 g/cm3

207.5-212 °C

594.4°C at 760 mmHg

2℃

118 ° (C=1, H2O)

soluble

2-8°C

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)

D24 +98.3 ± 1.4° (c = 1.002 in methanol)

196.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

III

6.1(b)

3249

3

22-40-36/37/38-36-20/21/22-11

36-45-36/37-26-16

DL0310000

Xn,Xi,F

P210-P261-P302 + P352 + P312-P304 + P340 + P312-P337 + P313-P403 + P235

H225-H302 + H312 + H332-H319

|Warning|H302 (99.15%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 118 companies from 15 notifications to the ECHA C&L Inventory.

Drug Information

Treatment of chronic anal fissure

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume. (See all compounds classified as Cardiovascular Agents.)

Aldizem

Diltiazem hydrochloride Use and Manufacturing

Methods of Manufacturing

The N-alkylated lactam (0.317 mmol), Ac2O (1 mmol), Et3N (2 mmol) and DMAP (0.03 mmol) taken in CH2Cl2 (5 mL) were heated at reflux under N2 for 3 h. The mixture was poured into ice water and brine was added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (10 mL). The combined organic layers were washed with 5percent NH4OH (5 mL) solution, dried (Na2SO4) and evaporated. The residue was dissolved in MeOH (2 mL) and treated with anhydrous HCl gas till pH was 2. Ether (3 mL) was added to the resulting solution. The precipitated solids were collected by filtration and washed with 10percent MeOH-ether to afford diltiazem hydrochloride (92percent yield).The N-alkylated lactam (0.317 mmol), Ac2O (1 mmol), Et3N (2 mmol) and DMAP (0.03 mmol) taken in CH2Cl2 (5 mL) were heated at reflux under N2 for 3 h. The mixture was poured into ice water and brine was added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (10 mL). The combined organic layers were washed with 5percent NH4OH (5 mL) solution, dried (Na2SO4) and evaporated. The residue was dissolved in MeOH (2 mL) and treated with anhydrous HCl gas till pH was 2. Ether (3 mL) was added to the resulting solution. The precipitated solids were collected by filtration and washed with 10percent MeOH-ether to afford diltiazem hydrochloride (92percent yield).

Uses

Peripheral Vasodilator

Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:451.0
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:450.1380062
Monoisotopic Mass:450.1380062
Topological Polar Surface Area:84.4
Heavy Atom Count:30
Complexity:565
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

Drug Function and Efficacy

By acting on the smooth muscle of the coronary and peripheral blood vessels and the atrioventricular node, inhibiting the influx of Ca2 into the cells, showing vasodilation and prolonging the conduction time of the atrioventricular node, it is effective for hypertension, arrhythmia, and angina pectoris. The specific effects include: 1. Effect on blood pressure: reduce hypertension, reduce peripheral vascular resistance and myocardial oxygen consumption, increase cardiac output, and reduce blood pressure and show sodium diuresis without reducing the blood flow of the brain, coronary arteries, and kidneys; 2. Effect on arrhythmia: prolong the conduction time, effective refractory period, and functional refractory period of the atrioventricular node, show effects on supraventricular tachyarrhythmia, and inhibit supraventricular tachyarrhythmia caused by atrial electrical stimulation; 3. Effect on myocardial ischemia: improve the balance of myocardial oxygen supply and demand (dilate the main coronary artery and side branches, increase blood flow to the ischemic part of the myocardium, and inhibit coronary artery spasm), and play a myocardial protective role (inhibit excessive influx of Ca2 into cells during myocardial ischemia, maintain cardiac function and myocardial energy metabolism, and reduce the infarct focus).

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • CHEMECA DRUGS PRIVATE LTD

    United States United States
    Active
  • Vasudha Pharma Chem Ltd

    United States United States
    Active
  • PIRAMAL PHARMA LTD

    United States United States
    Active

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