Showing Compound Amlodipine (FDB023590)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:03 UTC

Update date

2015-10-09 22:33:19 UTC

Primary ID

FDB023590

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Amlodipine

Description

Amlodipine is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell; A long acting dihydropyridine calcium channel blocker. It is effective in the treatment of angina pectoris and hypertension; in angina it improves blood flow to the myocardium.; Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell. [HMDB]

CAS Number

88150-42-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate	ChEBI
Amlodipine free base	ChEBI
Amlodipino	ChEBI
Amlodipinum	ChEBI
Norvasc	Kegg
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid	Generator
Amlodipine besilate	HMDB
Amlodipine besylate	HMDB
AMVAZ	HMDB
Istin	HMDB
Pelmec	HMDB
Racemic amlodipine	HMDB
Amlodipine, (+-)-isomer	HMDB
Amlodipine, (+-)-isomer, maleate (1:1)	HMDB
Amlodipine, (S)-isomer, maleate (1:1)	HMDB
Amlor	HMDB
Amlodipine, (R)-isomer	HMDB
Pfizer brand OF amlodipine besilate	HMDB
Amlodipine maleate	HMDB
Amlodipine maleate (1:1)	HMDB
Amlodis	HMDB
Astudal	HMDB
Mack brand OF amlodipine besilate	HMDB
Almirall brand OF amlodipine besilate	HMDB
Eczacibasi brand OF amlodipine besilate	HMDB
Racemic Amlodipine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.64	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.64 m³·mol⁻¹	ChemAxon
Polarizability	42.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H25ClN2O5

IUPAC name

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

InChI Identifier

InChI=1S/C20H25ClN2O5/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/h5-8,17,23H,4,9-11,22H2,1-3H3

InChI Key

HTIQEAQVCYTUBX-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC

Average Molecular Weight

408.876

Monoisotopic Molecular Weight

408.145199627

Classification

Description

Belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Dihydropyridinecarboxylic acid derivative
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Azacycle
Enamine
Ether
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Amine
Primary amine
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Primary aliphatic amine
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:2668 )
primary amino compound (CHEBI:2668 )
methyl ester (CHEBI:2668 )
monochlorobenzenes (CHEBI:2668 )
dihydropyridine (CHEBI:2668 )

Ontology

Disposition

Biological location:

Organ and components:

Skin

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Amlodipine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003r-9008000000-1fbca2d37d687cf7db0b	Spectrum
Predicted GC-MS	Amlodipine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amlodipine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4u-0192000000-988fbef9dd83defbfbe0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-002o-1392000000-3e9bc5dcf61b0f4cae6a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0092000000-ee62f2bc59215356e927	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-0191000000-f2696d00f557899608c4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - -1V, Positive	splash10-0a4u-0192000000-dbb503bf75ac45992a8c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4j-2029500000-6f84285a27a09d3975ad	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gw3-3189000000-2934b69ddcfba1ecb708	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ffx-3293000000-4459172f2e0c2c8495ef	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3007900000-5363cd8b8ca60ece4eea	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-4029200000-2a9e3badde424295bb13	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9085000000-7db6de7520133d8f4045	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1033900000-377f5862d692ece9b8b3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6019200000-246c2de5f16d1f940e93	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-7093000000-e5145c0579c14e90d8d7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0lxw-0049100000-fa18ab567110013335f8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zor-0029100000-79f4e839da15602ebfb0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-3495000000-4c7c1402fa10dd2c0919	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum