3,5-diethyl 4-{2-[(1E)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 73234
• Molecular Formular: C26H33NO6
• Molecular Mass: 455.54332
• Monoisotopic Mass: 455.23078778
• SMILES: c1cccc(c1C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC)/C=C/C(=O)OC(C)(C)C
• Canonical SMILES: CCOC(=O)C1=C(C)NC(=C(C1c1ccccc1/C=C/C(=O)OC(C)(C)C)C(=O)OCC)C
• InChI: InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+
• InChIKey: GKQPCPXONLDCMU-CCEZHUSRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diethyl 4-{2-[(1E)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: caldine; lacidipine
• Synonyms: Lacipil; Motens; Lacidipine; (E)-4-[2-[3-(1,1-Dimethylethoxy)-3-oxo-1-propenyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Diethyl Ester, GR-43659X, GX-1048, Caldine, Lacipil, Lacirex, Motens

Database IDs

• CAS Number: 103890-78-4
• PubChem SID: 162038154
• PubChem CID: 5311217

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.9171872
• LogD (pH = 7.4): 4.1805105
• Log P: 4.1851535
• Molar Refractivity: 129.9138 cm^3
• Polarizability: 49.212093 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White-to-Off-White Crystalline Solid
• Melting Point: 174-175°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: calcium channel

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1994

Research Area: Cancer
Biological Activity:
Lacidipine (Lacipil, Motens) is a L-type calcium channel blocker. Lacidipine (Lacipil, Motens) works by relaxing and opening up the blood vessels. [1] This allows blood to circulate more freely around the body, lowering blood pressure and allowing the heart to work more efficiently.Lacidipine (Lacipil, Motens) also inhibits Ca2+ (ER) efflux and enhances folding, trafficking, and activity of degradation-prone GC variants. Lacidipine (Lacipil, Motens) remodels mutated GC proteostasis by simultaneously activating a series of distinct molecular mechanisms, namely modulation of Ca2+ homeostasis, upregulation of the ER chaperone BiP, and moderate induction of the unfolded protein response. However, unlike previously reported proteostasis regulators, lacidipine (Lacipil, Motens) treatment is not cytotoxic but inhibits apoptosis induction typically associated with sustained activation of the unfolded protein response. [2] In another study, lacidipine pre-treatment prevents deterioration of motor nerve conduction velocity as compared to streptozotocin diabetic rats. Hyperalgesia induces by streptozotocin was antagonized by lacidipine (Lacipil, Motens). [3]References on Lacidipine (Lacipil, Motens)[1] http://en.wikipedia.org/wiki/Lacidipine, , [2] Chem Biol. , 2011 Jun 24, 18(6):766-76.[3] Arch Physiol Biochem., 2011 Feb, 117(1):12-7

Toronto Research Chemicals - L098000

A dihydropyridine calcium channel blocker. Antihypertensive.

REFERENCES

• Wang F, et al. Chem Biol. 2011 Jun 24;18(6):766-76.
• Safar, M., et al.: Clin. Pharmacol. Ther., 46, 94 (1989)
• Kharat, V.R., et al.: J. Pharm. Biomed. Anal., 28, 789 (1989)
• McCormack, A.J., et al.: Drugs, 63, 2327 (1989)