3-[1-(diphenylmethyl)azetidin-3-yl] 5-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 154044
• Molecular Formular: C33H34N4O6
• Molecular Mass: 582.64626
• Monoisotopic Mass: 582.24783483
• SMILES: CC1=C(C(C(=C(N1)N)C(=O)OC1CN(C1)C(c1ccccc1)c1ccccc1)c1cccc(c1)[N+](=O)[O-])C(=O)OC(C)C
• Canonical SMILES: CC(OC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC1CN(C1)C(c1ccccc1)c1ccccc1)N)C
• InChI: InChI=1S/C33H34N4O6/c1-20(2)42-32(38)27-21(3)35-31(34)29(28(27)24-15-10-16-25(17-24)37(40)41)33(39)43-26-18-36(19-26)30(22-11-6-4-7-12-22)23-13-8-5-9-14-23/h4-17,20,26,28,30,35H,18-19,34H2,1-3H3
• InChIKey: ZKFQEACEUNWPMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[1-(diphenylmethyl)azetidin-3-yl] 5-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: azelnidipine
• Synonyms: 2-Amino-1,4-dihydro-6-methyl-4-(3 nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) ester; 2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) ester; CS-905; Calblock; RS-9054; Azelnidipine; (±)-2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-[1-(Diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) Ester; Azelnidipine; CS 905; Calblock 3-[1-(Diphenylmethyl)-3-azetidinyl] 5-isopropyl (±)-2-Amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate; Azelnidipine

Database IDs

• CAS Number: 123524-52-7
• MDL Number: MFCD00865803
• PubChem SID: 162248183
• PubChem CID: 65948

CALCULATED PROPERTIES

• Acid pKa: 19.876219
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 4.7213326
• LogD (pH = 7.4): 5.5408096
• Log P: 5.5730386
• Molar Refractivity: 172.0605 cm^3
• Polarizability: 62.380646 Å^3
• Polar Surface Area: 137.03 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: powder

Safety Information

• RTECS: US7968332
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: Calcium Channel

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C33H34N4O6

DETAILS

Sigma Aldrich - A7106

Application
Azelnidipine is a novel dihydropyridine derivative, a L-type calcium channel blocker, and an antihypertensive. Acute administration of azelnidipine prevents a sudden drop of cardiac function after acute stress. Azelnidipine may have a protective role in inflammation associated with atherosclerosis.
Biochem/physiol Actions
Azelnidipine, a novel dihydropyridine derivative, is a L-type calcium channel blocker and antihypertensive. Unlike other L-type calcium channel blockers, azelnidipine causes minimal stimulation of the sympathetic nervous system despite its significant depressor effect. Azelnidipine may have a protective role in inflammation in atherosclerosis.

Toronto Research Chemicals - A808500

Azelnidipine is a dihydropyridine calcium channel blocker with antihypertensice activity. Azelnidipine is used for treating ischemic heart disease and cardiac remodeling after myocardial infarction. Studies show that Azelnidipine ttreatment can reduce the

REFERENCES

• Sugimoto, K. et al.: Int. J. Hypertens., No pp. (2010)
• Kain, V. et al.: Cardio. Diabetol., 9, 82 (2010)
• Kinouchi, K. et al.: Int. J. Hypertens., 284823, 11 (2010)