Diltiazem
Overview
Description
Diltiazem is a benzothiazepine derivative that functions as a calcium channel blocker. It is primarily used to treat cardiovascular conditions such as hypertension, chronic stable angina, and certain heart arrhythmias. This compound works by inhibiting the influx of calcium ions into cardiac and vascular smooth muscle cells, leading to vasodilation and reduced cardiac workload .
Scientific Research Applications
Diltiazem has a wide range of scientific research applications:
Chemistry: Used as a reference compound in analytical chemistry for the development of chromatographic methods.
Biology: Studied for its effects on calcium ion channels in various cell types.
Mechanism of Action
Target of Action
Diltiazem is a member of the non-dihydropyridine calcium channel blockers drug class . Its primary targets are the calcium channels in the cardiac and vascular smooth muscle . These channels play a crucial role in the contraction of the heart and blood vessels.
Mode of Action
This compound works by inhibiting the influx of calcium ions into cardiac and vascular smooth muscle during depolarization . This inhibition prevents the narrowing of blood vessels, promoting their dilation . Compared to other drugs in its class, this compound displays an intermediate specificity to target both the cardiac and vascular smooth muscle .
Biochemical Pathways
The primary biochemical pathway affected by this compound is the calcium signaling pathway . By blocking the calcium channels, this compound disrupts the normal flow of calcium ions, which are essential for muscle contraction. This leads to relaxation of the cardiac and vascular smooth muscle, resulting in vasodilation .
Pharmacokinetics
This compound is well absorbed from the gastrointestinal tract and is subject to an extensive first-pass effect . The absolute bioavailability of this compound, when given as an immediate-release oral formulation, is approximately 40% . This compound undergoes extensive hepatic metabolism .
Result of Action
The inhibition of calcium influx into the cardiac and vascular smooth muscle cells by this compound leads to vasodilation , which reduces blood pressure and increases blood flow . This makes this compound effective as an antihypertensive, anti-arrhythmic, and anti-anginal agent .
Action Environment
Environmental factors can influence the action of this compound. For instance, the presence of other drugs in the system can affect the metabolism and efficacy of this compound . Additionally, the pH level of the environment can impact the ionization state of this compound, potentially affecting its absorption and distribution . .
Safety and Hazards
Diltiazem can cause serious eye irritation and may cause damage to organs, particularly the cardiovascular system . It may cause an allergic skin reaction and is suspected of damaging fertility or the unborn child . It may cause harm to breast-fed children and is harmful to aquatic life . Repeated exposure may cause skin dryness or cracking .
Future Directions
Diltiazem is currently used to treat high blood pressure and to control angina (chest pain) . It is also used off-label for migraine prophylaxis, anal fissures, and pulmonary hypertension . The dosage of this compound is usually adjusted based on the patient’s condition and response to the medication . Future research may explore additional uses for this compound and further refine its dosing guidelines.
Biochemical Analysis
Biochemical Properties
Diltiazem primarily works by inhibiting the calcium influx into cardiac and vascular smooth muscle during depolarization . It interacts with the alpha-1 subunit of L-type calcium channels, displaying an intermediate specificity to target both the cardiac and vascular smooth muscle .
Cellular Effects
This compound has a profound effect on various types of cells and cellular processes. It relaxes the blood vessels, lowers blood pressure, and increases the supply of blood and oxygen to the heart while reducing its workload . In breast cancer cells, this compound has been shown to decrease colony formation and cell migration .
Molecular Mechanism
This compound exerts its effects at the molecular level primarily by inhibiting the calcium influx into cardiac and vascular smooth muscle during depolarization . It binds to the alpha-1 subunit of L-type calcium channels in a fashion somewhat similar to verapamil, another nondihydropyridine (non-DHP) calcium channel blocker .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound can change over time. For instance, it has been shown to produce increases in exercise tolerance, probably due to its ability to reduce myocardial oxygen demand . In cases of overdose, it can lead to severe conditions like hypotension, acidosis, anuria, type 1 respiratory failure, and persistent hypotension .
Dosage Effects in Animal Models
In hypertensive animal models, this compound reduces blood pressure and increases urinary output and natriuresis without a change in the urinary sodium/potassium ratio . The effects of this compound can vary with different dosages in animal models.
Metabolic Pathways
This compound is extensively metabolized in the liver via several pathways including N- and O-demethylation (via cytochrome P450), deacetylation (via plasma and tissue esterases), in addition to conjugation (via sulfation and glucuronidation) .
Transport and Distribution
This compound is well distributed in the body with an apparent volume of distribution of approximately 305 L . It is extensively metabolized in the liver with a systemic clearance of approximately 65 L/h .
Subcellular Localization
Given its mechanism of action, it can be inferred that this compound primarily localizes in the cell membrane where it interacts with L-type calcium channels to exert its effects .
Preparation Methods
Synthetic Routes and Reaction Conditions: Diltiazem can be synthesized through a multi-step process involving the reaction of various chemical intermediates. One common synthetic route involves the condensation of 2-(dimethylamino)ethyl chloride with 2-(4-methoxyphenyl)thioacetic acid to form the intermediate, which is then cyclized to produce this compound .
Industrial Production Methods: In industrial settings, this compound hydrochloride is prepared by dissolving this compound in water, followed by the addition of hydrochloric acid to form the hydrochloride salt. The solution is then filtered, concentrated, and crystallized to obtain pure this compound hydrochloride .
Chemical Reactions Analysis
Types of Reactions: Diltiazem undergoes various chemical reactions, including hydrolysis, oxidation, and reduction. One notable reaction is the hydrolysis of this compound to form desacetyl this compound, which occurs under acidic or basic conditions .
Common Reagents and Conditions:
Hydrolysis: Acidic or basic conditions
Oxidation: Oxidizing agents such as hydrogen peroxide
Reduction: Reducing agents such as sodium borohydride
Major Products:
Desacetyl this compound: Formed through hydrolysis
N-desmethyl this compound: Formed through N-demethylation
Comparison with Similar Compounds
Verapamil: Another calcium channel blocker with a similar mechanism of action but a different chemical structure.
Amlodipine: A dihydropyridine calcium channel blocker that primarily acts on vascular smooth muscle.
Comparison:
Diltiazem vs. Verapamil: Both compounds inhibit calcium influx in cardiac and vascular smooth muscle cells, but this compound has an intermediate specificity for both cardiac and vascular tissues, whereas verapamil primarily targets the heart muscle.
This compound vs. Amlodipine: this compound and amlodipine both cause vasodilation, but amlodipine has a longer half-life and primarily affects vascular smooth muscle, making it more suitable for long-term blood pressure control.
This compound’s unique intermediate specificity and its ability to target both cardiac and vascular smooth muscle make it a versatile and effective therapeutic agent for various cardiovascular conditions.
Properties
IUPAC Name |
[(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HSUGRBWQSSZJOP-RTWAWAEBSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CC(=O)O[C@@H]1[C@@H](SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C22H26N2O4S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID9022940 |
Source
|
| Record name | (+)-Diltiazem | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9022940 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
414.5 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Diltiazem | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014487 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Boiling Point |
Decomposes |
Source
|
| Record name | DILTIAZEM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6528 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Solubility |
Soluble in methanol or chloroform, In water, 465 mg/l @ 25 °C, 1.68e-02 g/L |
Source
|
| Record name | Diltiazem | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00343 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | DILTIAZEM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6528 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Diltiazem | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014487 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Excitation of cardiac muscle involves the activation of a slow calcium inward current that is induced by L-type slow calcium channels, which are voltage-sensitive, ion-selective channels associated with a high activation threshold and slow inactivation profile. L-type calcium channels are the main current responsible for the late phase of the pacemaker potential. Acting as the main Ca2+ source for contraction in smooth and cardiac muscle, activation of L-type calcium channels allows the influx of calcium ions into the muscles upon depolarization and excitation of the channel. It is proposed that this cation influx may also trigger the release of additional calcium ions from intracellular storage sites. Diltiazem is a slow calcium channel blocker that binds to the extracellular site of the alpha-1C subunit of the channel, which is thought to be the S5-6 linker region of the transmembrane domain IV and/or S6 segment of domain III. Diltiazem can get access to this binding site from either the intracellular or extracellular side, but it requires a voltage-induced conformational changes in the membrane. Diltiazem inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes. In isolated human atrial and ventricular myocardium, diltiazem suppressed tension over the range of membrane potentials associated with calcium channel activity but had little effect on the tension-voltage relations at more positive potentials. This effect is thought to be mediated by the voltage-dependent block of the L-type calcium channels and inhibition of calcium ion release from the ER stores, without altering the sodium-calcium coupled transport or calcium sensitivity of myofilaments. Through inhibition of inward calcium current, diltiazem exerts a direct ionotropic and energy sparing effect on the myocardium. Diltiazem fslows atrioventricular nodal conduction, which is due to its ability to impede slow channel function. Reduced intracellular calcium concentrations equate to increased smooth muscle relaxation resulting in arterial vasodilation and therefore, decreased blood pressure. 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. Through its actions on reducing calcium levels in cardiac and vascular smooth muscles, diltiazem causes a reduction in the contractile processes of the myocardial smooth muscle cells and vasodilation of the coronary and systemic arteries, including epicardial and subendocardial. This subsequently leads to increased oxygen delivery to the myocardial tissue, improved cardiac output due to increased stroke volume, decreased total peripheral resistance, decreased systemic blood pressure and heart rate, and decreased afterload. Diltiazem lowers myocardial oxygen demand through a reduction in heart rate, blood pressure, and cardiac contractility; this leads to a therapeutic effect in improving exercise tolerance in chronic stable angina., The effects of D-cis- and L-cis-diltiazem on the hydrogen peroxide (H2O2)-induced derangements of mechanical function and energy metab, and accumulation of intracellular Na+ were studied in isolated rat hearts. The intracellular concn of Na+ ([Na+]i) in the myocardium was measured using a nuclear magnetic resonance technique. H2O2 (600 uM) increased the left ventricular end-diastolic pressure, decreased the tissue level of ATP, and increased the release of lactate dehydrogenase from the myocardium. These alterations induced by H2O2 were significantly attenuated by D-cis-diltiazem (15 uM) or L-cis-diltiazem (15 uM). H2O2 (1 mM) produced a marked incr in the myocardial [Na+]i, which was effectively inhibited by ... D-cis-diltiazem (15 uM) or L-cis-diltiazem (15 uM). ... The protective action of D-cis- and L-cis-diltiazem may be due to their ability to inhibit the H2O2-induced incr in [Na+]i, at least in part. |
Source
|
| Record name | Diltiazem | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00343 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | DILTIAZEM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6528 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
White crystalline powder | |
CAS No. |
56209-45-1, 42399-41-7 |
Source
|
| Record name | dl-cis-Diltiazem | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=56209-45-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Diltiazem | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=42399-41-7 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Diltiazem [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0042399417 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | cis-3-Acetoxy-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0056209451 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Diltiazem | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00343 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | (+)-Diltiazem | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9022940 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Diltiazem | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.050.707 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
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| Record name | DILTIAZEM | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/EE92BBP03H | |
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| Record name | DILTIAZEM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6528 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Diltiazem | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014487 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
187-188, 212 °C (decomposes), 231 °C |
Source
|
| Record name | Diltiazem | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00343 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | DILTIAZEM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6528 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Diltiazem | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014487 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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