(3s)-1-Benzylpyrrolidin-3-yl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Basic information
- CAS
104713-75-9- Standard SMILES
COC(=O)C1=C(C)NC(C)=C(C(=O)O[C@H]2CCN(Cc3ccccc3)C2)C1c1cccc([N+](=O)[O-])c1- InChIKey
VXMOONUMYLCFJD-XADRRFQNSA-N- Molecular formula
- C27H29N3O6
- Average molar mass
- 491.5 g/mol
- Monoisotopic mass
- 491.20563565
Overview
See also: Barnidipine (annotation moved to).
Names & identifiers
- Preferred name
- (3s)-1-Benzylpyrrolidin-3-yl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- IUPAC
- 5-O-[(3S)-1-benzylpyrrolidin-3-yl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- English name
- Barnidipine
- Molecular formula
- C27H29N3O6
- Molecular weight
- 491.54
Names & synonyms
NCGC00181772-01SCHEMBL678277DTXSID20909147MFCD00871351(3s)-1-benzylpyrrolidin-3-yl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate5-O-[(3S)-1-benzylpyrrolidin-3-yl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateG783311-benzylpyrrolidin-3-yl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateO5-[(3S)-1-benzylpyrrolidin-3-yl] O3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateBARNIDIPINEBarnidipine-d5Barnidipine(b)
Show more names
YM-09730-5(Free base)Barnidipine USP/EP/BPBarnidipine, 10 mM in DMSOBarnidipine,Inhibitor,Ca2+ channels,Calcium Channel,inhibit,Ca channels(S)-3-((S)-1-Benzylpyrrolidin-3-yl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridin(S)-3-((S)-1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3(+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 114 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 917
Physicochemical properties
- Melting point
- 137 · 137-139°
- alpha
- 20 · D20 +64.8° (c = 1 in methanol)
- Boiling point
- 614.5 · 614.5±55.0 °C(Predicted)
- Density
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO
- pka
- 7.62 · 7.62±0.40(Predicted)
- FDA UNII
- 2 VBY96ASWJ · 2VBY96ASWJ
- ATC code
- 8 CA12 · C08CA12
Chemistry & industry
Applications
DescriptionBarnidipine is a long-acting novel calcium antagonist that belongs to the dihydropyridine (DHP) group of calcium channel blockers. It contains two chiral centres thus can have four possible enantiomers. The active component is composed of a single optical isomer (3'S, 4S configuration), which is the most potent and longest-acting of the four enantiomers. Barnidipine has shown to be an effective antihypertensive agent in the management of hypertension in elderly patients and its efficacy is not negatively affected by age.
UsesBarnidipine is used in the treatment of hypertension, barnidipine displays high affinity for the calcium channels of the smooth muscle cells in the vascular wall and selectivity against cardiovascular L-type calcium channels.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Barnidipine is a dihydropyridine.
Related reactions
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Compound notes
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