benzenesulfonic acid 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 44446
• Molecular Formular: C26H31ClN2O8S
• Molecular Mass: 567.05094
• Monoisotopic Mass: 566.14896464
• SMILES: C1(=C(NC(=C(C1c1c(Cl)cccc1)C(=O)OCC)COCCN)C)C(=O)OC.c1ccccc1S(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)c1ccccc1.NCCOCC1=C(C(=O)OCC)C(C(=C(N1)C)C(=O)OC)c1ccccc1Cl
• InChI: InChI=1S/C20H25ClN2O5.C6H6O3S/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21;7-10(8,9)6-4-2-1-3-5-6/h5-8,17,23H,4,9-11,22H2,1-3H3;1-5H,(H,7,8,9)
• InChIKey: ZPBWCRDSRKPIDG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzenesulfonic acid 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: amlodipine; benzenesulfonic acid
• Synonyms: Amlodipine besylate; 2-[(2-Aminoethoxy)-methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5- pyridinedicarboxylic acid 3-ethyl 5-methyl ester benzene sulfonate; Amlodipine besylate; 2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester Benzenesulfonate; Amdepin; Amdipin; Amlodin; UK 48340-26; Vazkor; Istin; Norvasc

Database IDs

• CAS Number: 111470-99-6; 88150-42-9
• MDL Number: MFCD00887594
• PubChem SID: 24890999; 162049209
• PubChem CID: 60496

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.366646
• LogD (pH = 7.4): -0.37164375
• Log P: 1.6355954
• Molar Refractivity: 108.6381 cm^3
• Polarizability: 41.695133 Å^3
• Polar Surface Area: 99.88 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥20 mg/mL; Ethanol; Methanol; Slightly Soluble in Water
• Apperance: white powder; White to Off-White Solid
• Melting Point: 198-200°C; 199-201°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: US7967700
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: >95%; ≥98% (HPLC)
• Salt Data: Besylate
• Empirical Formula (Hill Notation): C20H25ClN2O5 · C6H5SO3H

DETAILS

Selleck Chemicals - S1813

Research Area: Cardiovascular Disease
Biological Activity:
Amlodipine(Norvasc) is a long-acting calcium channel blocker with an IC50 of 1.9 nM.Amlodipine specifically inhibited bTREK-1 in a concentration-dependent manner with an IC50 of 0.43μM.At concentrations that produced near complete block of bTREK-1, amlodipine inhibited voltage-gated Kv1.4 K+ and T-type Ca2+currents in AZF cells by less than 10%. [1]Amlodipine was twice as potent as nifedipine at inhibiting Ca2+-induced contractions in depolarised rat aorta (IC50 1.9 nM vs. 4.1 nM) but, unlike nifedipine, displayed a very slow onset of action.Amlodipine also inhibited 35 mM KCl-induced contractions of pig coronary artery rings (IC50 = 2.2 x 10-8 M) and human coronary artery rings (IC50 = 2.1 x 10-8 M). [2]Hypertension (HTN) or high blood pressure is a cardiac chronic medical condition in which the systemic arterial blood pressure is elevated.Amlodipine besylate has been used for treating hypertension in Phase III. [3]Amlodipine besylate is originally developed by Pfizer.References on Amlodipine besylate (Norvasc)[1] JPET, 2007, 323:39–48,

Sigma Aldrich - A5605

Application
Amlodipine besylate is a L-type calcium channel blocker which may be used for the treatment of angina pectoris and hypertension. Amlodipine also inhibits growth of human epidermoid carcinoma A431 cells and has antireproductive effects in male rats.
Biochem/physiol Actions
Amlodipine is an L-type calcium channel blocker. Amlodipine belongs to a class of cardiovascular drugs, which act at the voltage gated calcium channel of the CaV1, or L-type, class. Amlodipine also has antihypertensive and antianginal effects. Its activity resides mainly in the (-)-isomer. Amlodipine inhibits growth of human epidermoid carcinoma A431 cells and has antireproductive effects in male rats.

Toronto Research Chemicals - A633500

A dihydropyridine calcium channel blocker. Used as an antianginal and antihypertensive.

REFERENCES

• http://www.drugbank.ca/drugs/DB00381
• Arrowsmith, J.E., et al.: J. Med. Chem., 29, 1696 (1986)
• Burges, R.A., et al.: J. Cardiovasc Pharmacol., 9, 110 (1986)
• Packer, M., et al.: N. Engl. J. Med., 335, 1107 (1986)