Pimobendan

Base Information

• Chemical Name: Pimobendan
• CAS No.: 74150-27-9
• Deprecated CAS: 118428-36-7
• Molecular Formula: C₁₉H₁₈N₄O₂
• Molecular Weight: 334.378
• Hs Code.: 2933995300
• European Community (EC) Number: 640-420-7
• UNII: 34AP3BBP9T,613JXV89SU,9HTU209Z0N
• DSSTox Substance ID: DTXSID8048280
• Nikkaji Number: J34.390K
• Wikipedia: Pimobendan
• Wikidata: Q414351
• NCI Thesaurus Code: C82305
• RXCUI: 1110783
• Pharos Ligand ID: 77HQC92HVYFM
• Metabolomics Workbench ID: 54482
• ChEMBL ID: CHEMBL24646
• Mol file: 74150-27-9.mol

Synonyms:4,5-dihydro-6-(2-(4-methoxyphenyl)-1H-benzimidazole-5-yl)-5-methyl-3(2H)-pyridazinone;pimobendan;pimobendane;UD CG 115;UD-CG 115;UD-CG115

Chemical Property of Pimobendan

Chemical Property:

• Melting Point: approximate 243℃ (dec.)
• Refractive Index: 1.692
• PKA: 10.55±0.10(Predicted)
• PSA: 79.37000
• Density: 1.36 g/cm³
• LogP: 2.86300
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 334.14297583
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

99%Min. ^*data from raw suppliers

rac Pimobendan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)NN=C1C2=CC3=C(C=C2)N=C(N3)C4=CC=C(C=C4)OC
• Recent NIPH Clinical Trials: Usefulness of Low-dose Pimobendan for Patients with Chronic Heart Failure
• Description: Pimobendan, a novel cardiotonic vasodilator, was introduced in Japan for the treatment of acute and mild to moderate chronic heart failure. It is a phosphodiesterase Ⅲ inhibitor and is able to enhance sensitization of myocardial contractile regulatory protein to calcium ions. The combination of these effects contribute to its inotropic activity. In patients with severe congestive heart failure, orally administered pimobendan improves cardiac index, stroke volume index, pulmonary wedge pressure, and systemic and pulmonary vascular resistance. Pimobendan is reported to be well tolerated and largely devoid of the proarrhythmic effects of classical phosphodiesterase Ill inhibitors. Studies also suggested that combination of the inotropic agent pimobendan with an ACE inhibitor such as enalapril may be superior to monotherapy for heart failure patients.
• Uses: Pimobendan is a cardiotonic agent. The study of the cardiotonic mechanism of Pimobendan using ventricular muscles from rabbits and guinea pigs suggests that Pimobendan acts by inhibiting phosphodiesterase III and potassium channel. The potent venodilating action of Pimobendan makes it a suitable treatment option for patients with congestive heart failure (CHF) as it also improves systemic vasoconstriction. Pimobendan is a selective inhibitor of PDE3 with IC50 of 0.32 μM. It is a drug with both inotropic and vasodilatory properties that is used for the treatment of var-ious cardiac diseases.

Technology Process of Pimobendan

There total 19 articles about Pimobendan 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: 93.8%

4-methoxy-benzaldehyde (123-11-5) + 6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one (136609-85-3,136609-86-4,74150-02-0) → pimobendan (118428-37-8,118428-38-9,74150-27-9)

Guidance literature:

With sodium metabisulfite; In N,N-dimethyl-formamide; at 110 - 115 ℃; for 1.5h; Product distribution / selectivity;

Reference yield: 91.0%

(5RS)-6-[1-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1H-benzimidazole-6-yl]-5-methyl-4,5-dihydro-3(2H)pyridazinone → pimobendan (118428-37-8,118428-38-9,74150-27-9)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetone; at 20 ℃; for 3h; Temperature;

Reference yield: 84.9%

6-(2-bromo-1H-benzo[d]imidazol-6-yl)-5-methyl-4,5-dihydropyridazin-3(2H)-one + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7) → pimobendan (118428-37-8,118428-38-9,74150-27-9)

Guidance literature:

6-(2-bromo-1H-benzo[d]imidazol-6-yl)-5-methyl-4,5-dihydropyridazin-3(2H)-one; With caesium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; N,N-dimethyl-formamide; at 80 - 85 ℃; for 12h; Inert atmosphere;

upstream raw materials:

4-chlorobenzaldehyde

6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

4-methoxy-benzaldehyde

6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

Downstream raw materials:

4,5-dihydro-6-(2-(4-methoxyphenyl)-1H-benzimidazol-5-yl)-5-methyl-3(2H)-pyridazinone hydrochloride

Refernces

• 1、 -. "Synthesis method of pimobendan". Paragraph 0015; 0070; 0076. . Retrieved 2020/08/29.
• 2、 -. "Chemical synthesis method of Pimobendan". Paragraph 0024; 0025; 0031; 0037; 0043; 0049. . Retrieved 2017/05/23.