Basic information
- CAS
86780-90-7- Standard SMILES
COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)=O)C1c1ccccc1[N+](=O)[O-]- InChIKey
NCUCGYYHUFIYNU-UHFFFAOYSA-N- Molecular formula
- C19H20N2O7
- Average molar mass
- 388.4 g/mol
- Monoisotopic mass
- 388.12705098
Overview
Aranidipine is an organic molecular entity.
Names & identifiers
- Preferred name
- Aranidipine
- IUPAC
- 3-O-methyl 5-O-(2-oxopropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- English name
- ARANIDIPINE
- Molecular formula
- C19H20N2O7
- Molecular weight
- 388.37
Names & synonyms
aranidipine86780-90-7SaprestaMpc-1304MPC1304DTXSID9048649Aranidipino3-METHYL 5-(2-OXOPROPYL) 2,6-DIMETHYL-4-(2-NITROPHENYL)-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE4Y7UR6X2PO3-O-methyl 5-O-(2-oxopropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateDTXCID6028575aranidipinum
Show more names
AsanidipineAranidipine MPC1304ARANIDIPINE USP/EP/BPAranidipine, 10 mM in DMSOARANIDIPINE MPC1304Calcium Channel,inhibit,MPC 1304,Inhibitor,MPC-1304,Aranidipine,Ca channels,Ca2+ channels
RefChem:559905methyl 2-oxopropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acidAranidipine [INN](+-)-Acetonyl methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(2-NITROPHENYL)-, 3-METHYL 5-(2-OXOPROPYL) ESTERNCGC00182054-02MPC 1304CAS-86780-90-7
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 128 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 748
Experimental & physicochemical properties
SolubilityInsoluble
Melting Point149-150ºC
Physicochemical properties
- Melting point
- 155 ° · 155°
- Boiling point
- 530 · 530.0±50.0 °C(Predicted)
- Density
- 1.284 · 1.284±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 125 mg/mL · DMSO : 125 mg/mL (321.86 mM)
- form
- Solid
- pka
- 2.56 · 2.56±0.70(Predicted)
- color
- Light yellow to yellow
- FDA UNII
- 4 Y7UR6X2PO · 4Y7UR6X2PO
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in male, female mice, rats (mg/kg): 143, 193, 1982, 1459 orally; LD50 in male, female mice (mg/kg): 7.3, 9.1 i.p. (Nakano)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302+H312+H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501
Chemistry & industry
Pharmacology
Protein Binding
The binding ratio of plasma proteins of aranidipine varies from 84-95%. This ratio of the drug is similar to the unchanged form and for the M-1 metabolite. Most of the binding happens towards serum albumin and a lower amount corresponds to the alpha1-acid glycoprotein.
Pharmacodynamics
Pre-clinical studies with aranidipine and its two metabolites have shown production of increases in femoral blood flow. It has been shown to present potent and long-lasting vasodilating actions. Aranidipine and its metabolites are shown to inhibit calcium-induced contraction in isolated rabbit arteries. Studies have shown that aranidipine is more potent to reduce blood pressure than other dihydropyridines. Aranidipine produce changes in renal blood flow, this effect may be explained by its effect on alpha-2-adrenoreceptor-mediated vasoconstriction.
Mechanism of Action
The high potential of aranidipine is thought to be related to the additional calcium antagonistic activity of its metabolite. The mechanism is thought to be related to the capacity of aranidipine and its metabolites to vasodilate afferent and efferent arterioles. this action is performed through the inhibition of voltage-dependent calcium channels. The typical mechanism of action of aranidipine, as all dihydropyridines, is based on the inhibition of L-type calcium channels, decreasing calcium concentration and inducing smooth muscle relaxation. It is a selective alpha2-adrenoreceptor antagonist which inhibits vasoconstrictive responses.
Biological Half-LifeThe elimination half-life of aranidipine and the M-1 metabolite are 1.1-1.2 hour and 2.7-3.5 hour respectively.
Metabolism/MetabolitesEight metabolites of aranidipine were found after oral administration. These metabolites were brought by a reduction of the ketone group, oxidation of dihydropyridine ring and de-esterification at the C-3 position.
Absorption, Distribution and Excretion
After administration, aranidipine is rapidly absorbed from the gastrointestinal tract. After absorption, the AUC and Cmax increased linearly in a dose-dependent manner, the Cmax was attained in approximate 3.8-4.8 hours for aranidipine and 4.8-6 hours for the metabolite M-1. The bioavailability of aranidipine in rat, dog, and monkey was about 48%, 41% and 3% respectively.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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