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A5605

Sigma-Aldrich

Amlodipine besylate

≥98% (HPLC)

Synonym(s):

2-[(2-Aminoethoxy)-methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5- pyridinedicarboxylic acid 3-ethyl 5-methyl ester benzene sulfonate, Norvasc

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About This Item

Empirical Formula (Hill Notation):
C20H25ClN2O5 · C6H5SO3H
CAS Number:
111470-99-6
Molecular Weight:
567.05
MDL number:
MFCD00887594
UNSPSC Code:
12352200
PubChem Substance ID:
24890999
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: ≥20 mg/mL

SMILES string

OS(=O)(=O)c1ccccc1.CCOC(=O)C2=C(COCCN)NC(C)=C(C2c3ccccc3Cl)C(=O)OC

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)

InChI key

ZPBWCRDSRKPIDG-UHFFFAOYSA-N

Gene Information

human ... CACNA1C(775) , CACNA1D(776) , CACNA1F(778) , CACNA1S(779)

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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.

Features and Benefits

This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dean J Kereiakes et al.
Journal of clinical hypertension (Greenwich, Conn.), 14(3), 149-157 (2012-03-01)
J Clin Hypertens (Greenwich). 2012;14:149-157. ©2012 Wiley Periodicals, Inc. Most patients with hypertension require combination therapy in order to achieve blood pressure (BP) goals. This 40-week open-label extension of the 12-week double-blind Triple Therapy With Olmesartan Medoxomil, Amlodipine, and Hydrochlorothiazide
Sheyanth Mohanakumar et al.
Lymphatic research and biology, 18(2), 156-165 (2019-08-21)
Background: The current belief is that the calcium channel blocker (CCB)-induced edema is due to a preferential arterial over
Gha-Hyun J Kim et al.
Scientific reports, 11(1), 23670-23670 (2021-12-10)
Among cases of SARS-CoV-2 infections that result in serious conditions or death, many have pre-existing conditions such as hypertension and are on renin-angiotensin-aldosterone system (RAAS) inhibitors. The angiotensin-converting-enzyme-2 (ACE2), a key protein of the RAAS pathway, also mediates cellular entry
L-type calcium channel blocker increases VEGF concentrations in retinal cells and human serum.
Kumar, et al.
PLoS ONE, 18, e0284364-e0284364 (2023)
Emanuele Muraca et al.
Diabetes/metabolism research and reviews, 37(3), e3389-e3389 (2020-08-02)
Hypothalamus-pituitary-adrenal (HPA) axis hyperactivity was suggested to be associated with the metabolic syndrome (MS), obesity and diabetes. The aim of this study was to test whether hypercortisolism was associated with altered glucose homeostasis and insulin resistance, hypertension and dyslipidemia in
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