Diltiazem

Base Information

• Chemical Name: Diltiazem
• CAS No.: 42399-41-7
• Molecular Formula: C22H26N2O4S
• Molecular Weight: 414.525
• European Community (EC) Number: 255-796-4
• UNII: EE92BBP03H
• DSSTox Substance ID: DTXSID9022940
• Nikkaji Number: J16.566B
• Wikipedia: Diltiazem
• Wikidata: Q422229
• NCI Thesaurus Code: C61725
• RXCUI: 3443
• Pharos Ligand ID: CV8BFLDQ99B6
• Metabolomics Workbench ID: 42720
• ChEMBL ID: CHEMBL23
• Mol file: 42399-41-7.mol

Synonyms:Aldizem;Cardil;Cardizem;CRD 401;CRD-401;CRD401;Dilacor;Dilacor XR;Dilren;Diltiazem;Diltiazem Hydrochloride;Diltiazem Malate;Dilzem;Tiazac

Chemical Property of Diltiazem

Chemical Property:

• Boiling Point: 594.4 °C at 760 mmHg
• PKA: pKa 7.70 (Uncertain)
• Flash Point: 313.3 °C
• PSA: 84.38000
• Density: 1.26 g/cm³
• LogP: 3.43350
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 414.16132849
• Heavy Atom Count: 29
• Complexity: 565

Purity/Quality:

Diltiazem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC
• 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
• Recent ClinicalTrials: Efficiency of Antagonist Drugs of the Cellular Transcriptomic Signature of Influenza A Virus Infection.
• Recent EU Clinical Trials: PROgnostic value of precision medicine in patients with Myocardial Infarction and non-obStructive coronary artEries: the PROMISE study.
• Recent NIPH Clinical Trials: Comparing three drugs for reducing heart rate and blood pressure during laryngoscopy andintubation
• Uses: It is used for stable and nonstable angina pectoris (including after myocardial infarctions) as well as in arterial hypertension. Diltiazem is a potent vasodilator compound. Antihypertensive.
• Therapeutic Function: Coronary vasodilator
• 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.

Technology Process of Diltiazem

There total 28 articles about Diltiazem which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.2%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + cis-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one (42399-51-9) + butanone (78-93-3) → cis-(+)-3-hydroxy-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-2-(4-methoxyphenyl-1,5-benzothiazepine-4(5H)-one + diltiazem (42399-41-7)

Guidance literature:

With acetic anhydride; potassium carbonate; In water;

Reference yield: 90.0%

O-desacetyldiltiazem (42399-40-6) + acetic anhydride (108-24-7) → diltiazem (42399-41-7)

Guidance literature:

With dmap; In dichloromethane; for 5h; Heating;

DOI:10.1055/s-2003-42397

Reference yield: 85.0%

diltiazem hydrochloride (33286-22-5) → diltiazem (42399-41-7)

Guidance literature:

With sodium carbonate; In water; for 0.333333h;

DOI:10.1016/j.ijpharm.2021.120790

upstream raw materials:

(+/-)-Diltiazem

O-desacetyldiltiazem

acetic anhydride

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Downstream raw materials:

{2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-ethyl-dimethyl-ammonium; bromide

{2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-dimethyl-propyl-ammonium; bromide

L-cis-diltiazem

N-desmethyldiltiazem

Refernces

• 1、 Diniz, Luan F.,Franco, Chris H.J.,Silva, Daniely F.,Martins, Larissa S.,Carvalho Jr, Paulo S.,Souza, Mateus A.C.,Reis, Naialy F.A.,Fernandes, Christian,Diniz, Renata. "Multicomponent ionic crystals of diltiazem with dicarboxylic acids toward understanding the structural aspects driving the drug-release". . . Retrieved 2021.
• 2、 Ivanova, Nadezhda Antonova,Trapani, Adriana,Franco, Cinzia Di,Mandracchia, Delia,Trapani, Giuseppe,Franchini, Carlo,Corbo, Filomena,Tripodo, Giuseppe,Kolev, Iliyan Nikolov,Stoyanov, Georgi Stoyanov,Bratoeva, Kameliya Zhechkova. "In vitro and ex vivo studies on diltiazem hydrochloride-loaded microsponges in rectal gels for chronic anal fissures treatment". . p. 53 - 65. Retrieved 2019.