3-(3R)-1-benzylpiperidin-3-yl 5-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

• ChemBase ID: 73229
• Molecular Formular: C28H32ClN3O6
• Molecular Mass: 542.02318
• Monoisotopic Mass: 541.19796344
• SMILES: c1([C@H]2C(=C(NC(=C2C(=O)OC)C)C)C(=O)O[C@@H]2CCCN(C2)Cc2ccccc2)cc(ccc1)[N+](=O)[O-].Cl
• Canonical SMILES: COC(=O)C1=C(C)NC(=C([C@@H]1c1cccc(c1)[N+](=O)[O-])C(=O)O[C@@H]1CCCN(C1)Cc1ccccc1)C.Cl
• InChI: InChI=1S/C28H31N3O6.ClH/c1-18-24(27(32)36-3)26(21-11-7-12-22(15-21)31(34)35)25(19(2)29-18)28(33)37-23-13-8-14-30(17-23)16-20-9-5-4-6-10-20;/h4-7,9-12,15,23,26,29H,8,13-14,16-17H2,1-3H3;1H/t23-,26-;/m1./s1
• InChIKey: KILKDKRQBYMKQX-MIPPOABVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3R)-1-benzylpiperidin-3-yl 5-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• IUPAC Traditional name: benidipino hydrochloride; benidipine hydrochloride
• Synonyms: KW-3049; (4R)-rel-3,5-Pyridinedicarboxylic acid; 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-; 3-methyl 5-[(3R)-1-(phenylmethyl)-3-piperidinyl] ester; hydrochloride (1:1); Benidipine hydrochloride; Benidipine hydrochloride; (4R)-rel-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-[-1-(Phenylmethyl)-3-piperidinyl] Ester Hydrochloride; (+/-)-Benidipine Hydrochloride; Coniel; KW 3049; rac Benidipine Hydrochloride; (4R)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-[(3R)-1-(Phenylmethyl)-3-piperidinyl] Ester Monohydrochloride; R-(R*,R*)]- 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 1-(Phenylmethyl)-3-piperidinyl Ester Hydrochloride; (R,R)-KW 3049; (-)-α-Benidipine Hydrochloride

Database IDs

• CAS Number: 91599-74-5; 129262-07-3
• PubChem SID: 162038149
• PubChem CID: 656667

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.1523023
• LogD (pH = 7.4): 3.1822286
• Log P: 4.0241766
• Molar Refractivity: 142.0076 cm^3
• Polarizability: 53.505726 Å^3
• Polar Surface Area: 113.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥20 mg/mL; Ethanol; Methanol; Water
• Apperance: yellow powder; Yellow Solid
• Melting Point: 199-201°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: US7975657
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: calcium channel

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: hydrochloride
• Empirical Formula (Hill Notation): C28H31N3O6·HCl

DETAILS

Selleck Chemicals - S2017

Research Area: cancer
Biological Activity:
Benidipine hydrochloride is a hydrochloride salt form of benidipine which is a dihydropyridine calcium channel blocker. [1] Benidipine hydrochloride is used for the treatment of high blood pressure (hypertension). Benidipine hydrochloride reveals a wide range of activities in vitro and in vivo. Benidipine hydrochloride inhibits L-, N- and T-type Ca2+ channels. Benidipine hydrochloride also prevents aldosterone- induced mineralocorticoid receptor activation. Benidipine hydrochloride exhibits cardioprotective and antiartherosclerotic effects. [2]References on Benidipine HCl[1] http://en.wikipedia.org/wiki/Benidipine, , [2] Eur J Pharmacol., 2010, 635(1-3):49-55

Sigma Aldrich - B6813

Biochem/physiol Actions
Calcium Channel Blocker

Toronto Research Chemicals - B157490

The R-enantiomer of Benidipine (B157500). A dihydropyridine calcium channel blocker. Antihypertensive.

Toronto Research Chemicals - B157500

A dihydropyridine calcium channel blocker. Antihypertensive.

REFERENCES

• Kosaka H,et al. Eur J Pharmacol. 2010;635(1-3):49-55.
• Suzuki, T., et al.: Cardiovasc. Drug Rev., 7, 25 (1989)
• Hirayama, N., et al.: Acta Crystallogr., C47, 458 (1989)
• Akizuki, O., et al.: Eur. J. Pharmacol., 584, 424 (1989)
• Suzuki, T., et al.: Cardiovasc. Drug Rev., 7, 25 (1989)
• Hirayama, N., et al.: Acta Crystallogr., C47, 458 (1989)