89226-75-5

Basic information

• Product Name: Manidipine hydrochloride
• Synonyms: 4-(diphenylmethyl)-1-piperazinyl)ethylmethylester,dihydrochloride;cv-4093dihydrochlorde;franidipinehydrochloride;MANIDIPINE DIHYDROCHLORIDE;MANIDIPINE HYDROCHLORIDE;1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl methyl ester hydrochloride;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl methyl ester, dihydrochloride (9CI);Calslot
• CAS NO: 89226-75-5
• Molecular Formula: C₃₅H₃₈N₄O₆*2ClH
• Molecular Weight: 683.62
• EINECS: 1308068-626-2
• Product Categories: Antihypertensive
• Mol File: 89226-75-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 157-163°; mp 174-180°; mp 167-170°
• Boiling Point: 722 °C at 760 mmHg
• Flash Point: 390.4 °C
• Appearance: /
• Vapor Pressure: 1.07E-20mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in DMSO (>25 mg/ml)
• Water Solubility: Soluble in DMSO. Slightly soluble in water and ethanol /n
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• Merck: 14,5743
• CAS DataBase Reference: Manidipine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Manidipine hydrochloride(89226-75-5)
• EPA Substance Registry System: Manidipine hydrochloride(89226-75-5)

Safety Data

• RIDADR: UN 2811 6.1/PG III
• RTECS: US7975300
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 89226-75-5(Hazardous Substances Data)

Usage

Description

Manidipine hydrochloride is a dihydropyridine calcium channel blocker with high selectivity for vasculature, exhibiting antihypertensive properties. It is a clinically useful antihypertensive agent and has been found to inhibit the SARS-CoV-2 main protease, 3CLpro, as well as act as an early entry inhibitor of human cytomegalovirus by inhibiting the Immediate-Early 2 (IE2) protein.

Uses

Used in Pharmaceutical Industry:
Manidipine hydrochloride is used as an aldosterone antagonist for the treatment of hypertension. It helps in lowering blood pressure by relaxing blood vessels and improving blood flow.
Manidipine hydrochloride is used as an antihypertensive agent for managing high blood pressure. Its dihydropyridine calcium channel blocking properties allow it to selectively target vasculature, leading to a reduction in blood pressure.
Used in Antiviral Applications:
Manidipine hydrochloride is used as an inhibitor of the SARS-CoV-2 main protease, 3CLpro, for potential treatment of COVID-19. Its ability to inhibit this protease may help in limiting the replication of the virus.
Manidipine hydrochloride is used as an early entry inhibitor of human cytomegalovirus by inhibiting the Immediate-Early 2 (IE2) protein. This application may help in preventing the virus from entering and infecting host cells, thus limiting the spread of the infection.

References

Kakihana et al. (1988), Antihypertensive effect of CV-4093·2HCl, a new calcium antagonist, in three rat models of hypertension; Jpn. J. Pharmacol., 48 223 McKeage (2004), Manidipine: a review of its use in the management of hypertension; Drugs, 64 1923 Ghahremanpour et al. (2020), Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2; ACS Med. Chem. Lett., 11 2526 Mercorelli et al. (2018), Repurposing the clinically approved calcium antagonist manidipine dihydrochloride as a new early entry inhibitor of human cytomegalovirus targeting the Immediate-Early 2 (IE2) protein; Antiviral Res., 150 130

InChI:InChI=1/C35H38N4O6.ClH/c1-24-30(34(40)44-3)32(28-15-10-16-29(23-28)39(42)43)31(25(2)36-24)35(41)45-22-21-37-17-19-38(20-18-37)33(26-11-6-4-7-12-26)27-13-8-5-9-14-27;/h4-16,23,32-33,36H,17-22H2,1-3H3;1H

Upstream product

• 10527-64-7 1-diphenylmethyl-4-(2-hydroxyethyl)piperazine 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 126451-47-6 (S)-Manidipine 
• 76093-37-3 (4R)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 
• 76093-31-7 1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid 
• 76093-33-9 (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 76093-32-8 (4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 
• 76093-34-0 (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 841-77-0 diphenylmethylpiperazine 
• 89226-50-6 manidipine 
• 89226-49-3 2-(4-diphenylmethyl-1-piperazinyl)ethyl acetoacetate 
• 39562-17-9 methyl 2-(3-nitrophenylmethylene)acetoacetate 
• 90096-33-6 2-(4-diphenylmethyl-1-piperazinyl)ethyl 3-aminocrotonate 

Downstream Products

• 89226-50-6 manidipine 
• 120092-68-4 (R)-Manidipine 
• 126451-47-6 (S)-Manidipine 
• 104305-93-3 2-(4-diphenylmethyl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-dicarboxylate 

Relevant articles and documents

Improved manidipine dihydrochloride II crystal form production method

The invention discloses an improved manidipine dihydrochloride II crystal form production method. The method comprises the steps: adding concentrated grease containing manidipine alkali into ethyl alcohol, stirring to befor crystallizedcrystallizing, filtering to obtain filter cake and pulping and washing to obtain the manidipine alkali; then utilizing hydrochloric acid salification to obtain a manidipine dihydrochloride crude product; heating and dissolving the manidipine dihydrochloride crude product by methyl alcohol containing water, performing thermal-insulation filtration, crystallization and filtration, collecting separated-out crystal and drying to obtain the manidipine dihydrochloride II crystal form. The purity of the II crystal form obtained by the production method disclosed bythe invention is larger than 99.8%, and the method has very great guiding significance in researches of the manidipine dihydrochloride crystal form and clinical application of manidipine dihydrochloride.

S-Manidipine hydrochloride crystal form I and preparation method thereof

The invention relates to an S-Manidipine hydrochloride crystal form I and a preparation method thereof. The preparation method includes: dissolving S-Manidipine free alkali into alcohols or alcohol/water, salifying with HCL, and crystallizing to obtain S-Manidipine hydrochloride crystal which is determined as the crystal form I according to X-ray powder diffraction detection. Products of the S-Manidipine hydrochloride crystal form I have excellent temperature and humidity stability, meet quality requirements on residual solvent and moisture and are suitable for preparation process and long-term storage. Pharmaceutical compositions with compounds of the crystal form I serving as active ingredients can be used for treating diseases such as hypertension and the like.

POLYMORPHIC FORMS OF MANIDIPINE

The invention relates to various new polymorphic forms of manidipine and pharmaceutically acceptable salts thereof. The invention also relates to processes for the preparation of the polymorphic forms of manidipine and pharmaceutically acceptable salts thereof.