109545-30-4

Basic information

• Product Name: (S)-Nilvadipine
• Synonyms: (S)-(-)-Nilvadipine;(S)-Nilvadipine;3,5-Pyridinedicarboxylic acid, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester, (4S)- (9CI);3,5-Pyridinedicarboxylic acid, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester, (S)-
• CAS NO: 109545-30-4
• Molecular Formula: C19H19 N3 O6
• Molecular Weight: 0
• Mol File: 109545-30-4.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Nilvadipine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Nilvadipine(109545-30-4)
• EPA Substance Registry System: (S)-Nilvadipine(109545-30-4)

Safety Data

• Hazardous Substances Data: 109545-30-4(Hazardous Substances Data)

Usage

General Description

(S)-Nilvadipine is a calcium channel blocker used in the treatment of hypertension and other cardiovascular diseases. It works by dilating blood vessels and reducing the workload on the heart, thereby lowering blood pressure and improving blood flow. It belongs to the dihydropyridine class of calcium channel blockers and is specifically an enantiomer of nilvadipine. It has been shown to have a longer duration of action than other calcium channel blockers and has potential neuroprotective effects, making it a potential candidate for the treatment of neurodegenerative diseases such as Alzheimer's. Overall, (S)-Nilvadipine is a promising drug with multiple potential applications in the treatment of cardiovascular and neurological conditions.

Upstream product

• 497-19-8 sodium carbonate 
• 113201-61-9 2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-m-nitrophenylpyridine-5-carboxylic acid 
• 1452166-70-9 isopropyl 2-hydroxyiminomethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 67-63-0 isopropyl alcohol 
• 186581-53-3 diazomethane 
• 138279-20-6 (S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid 
• 138279-16-0 bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 122417-22-5 (R)-2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-5-pyridinecarboxylate 
• 158612-42-1 (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 158612-43-2 (R)-methyl pivaloyloxymethyl 2-bromomethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 158612-41-0 (R)-methyl pivaloyloxymethyl 2-formyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 87730-99-2 4-acetoxy-3-oxo-butyric acid methyl ester 
• 191742-12-8 isopropyl 2-acetoxymethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3-methoxycarbonyl-5-piperidinecarboxylate 
• 153219-23-9 (S)-isopropyl 2-hydroxymethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3-methoxycarbonyl-5-piperidinecarboxylate 

Downstream Products

• 145220-90-2 isopropyl 6-acetoxymethyl-2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)pyridine-5-carboxylate 
• 145220-89-9 2-cyano-5-isopropoxycarbonyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-N-oxide 
• 145220-88-8 methyl 2-cyano-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>pyridine-3-carboxylate 

Relevant articles and documents

Studies on nilvadipine. IV. Synthesis of deuteriated and optically active isopropyl 2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridi ne-5-carboxylate (nilvadipine)

Nilvadipine, I, has already entered clinical use for the treatment of hypertension. In the process of the developing nilvadipine, we prepared the deuteriated analogue of I as an internal standard for the determination of I in human plasma by capillary column gas chromatography-negative-ion chemical-ionization mass spectrometer. Nilvadipine has an asymmetric center at the C-4 position of the dihydropyridine ring, and characterization of the optical isomers with regard to their activity and bioavailability is of interest. Thus, we synthesized both the enantiomers of I by optical resolution via the 5-carboxy derivative (3), which was previously prepared as one of the metabolites of I.

Ac2O/K2CO3/DMSO: An efficient and practical reagent system for the synthesis of nitriles from aldoximes

The transformation of aldoximes to nitriles using acetic anhydride as dehydration agent under mild reaction conditions is reported. The reaction, which proceeds under weak alkaline condition, allows for the conversion of a range of aldoximes including aromatic aldoximes, alphatic aldoximes, and heterocyclic aldoximes in good to excellent yields. This method has also been successfully applied to the synthesis of calcium channel blocker nilvadipine in pilot scale.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.