Nifedipine

Identification

Molecular formula

C₁₇H₁₈Cl₂N₂O₆

CAS number

21829-25-4

IUPAC name

O5-ethyl O3-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

State

At room temperature, Nifedipine is a solid. It is often found in the form of tablets for medication but in its pure form, it appears as a yellow crystalline powder.

Melting point (Celsius)

172.50

Melting point (Kelvin)

445.65

Boiling point (Celsius)

337.00

Boiling point (Kelvin)

610.15

General information

Molecular weight

346.33g/mol

Molar mass

346.3260g/mol

Density

1.4200g/cm³

Appearence

Nifedipine is typically a yellow crystalline powder. It is known for its distinctive yellow color which can be used as an identifying feature in its solid form.

Comment on solubility

Solubility Characteristics of O₅-ethyl O₃-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

The solubility of O₅-ethyl O₃-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (C₁₇H₁₈Cl₂N₂O₆) can be complex due to its unique molecular structure. Understanding solubility is crucial for applications in pharmacology and chemical formulation, as it affects both distribution and bioavailability. Here are several points to consider:

Polar vs. Non-Polar: The presence of multiple functional groups, including carboxylate, heavily influences the solubility. Generally, compounds featuring polar functional groups tend to be more soluble in polar solvents such as water.
Effect of Chlorine Atoms: The inclusion of chlorine atoms can enhance lipophilicity, making the compound potentially less soluble in water yet more soluble in organic solvents.
Influence of Substituents: The arrangement of alkyl groups and the dichlorophenyl moiety can also significantly alter solubility profiles, affecting how the compound interacts with solvents.
Temperature Dependency: Like many organic compounds, the solubility may increase with temperature, allowing for more comprehensive studies on its saturation points.

According to qualitative analyses, it may be anticipated that O₅-ethyl O₃-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate exhibits moderate to low solubility in aqueous environments but better solubility in organic solvents like ethanol or dichloromethane. As with many pharmaceuticals, a thorough understanding of solubility will facilitate the appropriate selection of solvents for synthesis and formulation processes. Thus, solubility is not merely a property but a critical parameter that directs the use and development of this compound in various applications.

Interesting facts

Interesting Facts about O⁵-ethyl O³-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

This compound is a unique member of the dihydropyridine family, known for its interesting pharmacological properties. Dihydropyridines are widely studied for their ability to act as calcium channel blockers, which makes them important in the treatment of cardiovascular diseases. Below are some intriguing aspects of this particular dihydropyridine derivative:

Pharmacological Potential: Compounds like this one often demonstrate potential as antihypertensive agents. The incorporation of dichlorophenyl groups is known to enhance their activity.
Versatile Synthesis: The synthetic pathway leading to this compound usually involves steps that allow for high versatility, accommodating various substitutions that can modulate its physical and chemical properties.
Chirality and Isomerism: The presence of multiple chiral centers offers opportunities for the exploration of stereoisomerism, which can vastly alter the biological activity of each isomer.
Research Implications: This compound has been a subject of research in designing selective drugs targeting specific ion channels, showcasing the importance of structure-activity relationships in medicinal chemistry.

As a chemistry student or professional, studying such complex compounds can greatly enhance one's understanding of organic synthesis and drug design. The careful manipulation of functional groups in dihydropyridines is not just an exercise in synthetic chemistry but a crucial step towards developing effective therapeutic agents. As one researcher noted, "A small change in structure can lead to dramatically different biological effects.”

In summary, O⁵-ethyl O³-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate stands as an exemplary model of how organic chemistry can intersect with medicinal applications, acting as a bridge between theoretical investigation and practical health solutions.

Synonyms

felodipine

72509-76-3

Plendil

Flodil

Splendil

Feloday

Munobal

Renedil

dl-Felodipine

Hydac

Modip

Perfudal

Prevex

Agon

Plendil ER

Felodipina

Felogard

Penedil

Preslow

Munobal Retard

Plendil Retard

Plendil Depottab

Felodipinum

Felodur ER

AGON SR

Plandil

Felodipinum [INN-Latin]

3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Felodipina [INN-Spanish]

H 154/82

Felodipino

UNII-OL961R6O2C

NSC-760343

BRN 4331472

OL961R6O2C

4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester

Felodipine (Plendil)

DTXSID4023042

(R)-(+)-Felodipine

C08CA02

CHEBI:585948

(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

MFCD00868316

H-154/82

(S)-(-)-Felodipine

3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

5-O-ethyl 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

MLS000069629

DTXCID303042

3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester

LEXXEL COMPONENT FELODIPINE

Felodipine [USAN:USP:INN:BAN]

ethyl methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

NSC 760343

NCGC00015455-03

SMR000058204

Felodipinum (INN-Latin)

C18H19Cl2NO4

119945-59-4

Felodipina (INN-Spanish)

FELODIPINE (MART.)

FELODIPINE [MART.]

(+/-)-ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

(S)-(-)-Felodipine-d5

4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylic acid ethyl methyl ester

FELODIPINE (USP-RS)

FELODIPINE [USP-RS]

3,5-Pyridinedicarboxylic acid, 1,4-dihydro-4-(2,3-dichlorophenyl)-2,6-dimethyl-, ethyl methyl ester

3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (+-)-

FELODIPINE (EP MONOGRAPH)

FELODIPINE (USP IMPURITY)

FELODIPINE [EP MONOGRAPH]

Felodipine [USAN:BAN:INN]

FELODIPINE [USP IMPURITY]

FELODIPINE (USP MONOGRAPH)

FELODIPINE [USP MONOGRAPH]

Logimax

Felodipine (USAN:USP:INN:BAN)

Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

(RS)-3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

3,5-PYRIDINEDICARBOXYLIC ACID 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-, ETHYL METHYL ESTER, (+/-)-

Ethyl methyl (4RS)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Plendil (TN)

(R)-(+)-Felodipine-d5

SR-01000075890

1217716-73-8

Felopdipine

Perfuda

Plendil;Renedil

Felodipine, solid

CGH-869

Felodipine,(S)

1217744-87-0

3,5-dicarboxylate

4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester;Feloday;Flodil

Prestwick_797

CAS-72509-76-3

Felodipine (dl form)

Felodipine (Standard)

FELODIPINE [MI]

FELODIPINE [INN]

FELODIPINE [JAN]

Opera_ID_1873

Prestwick0_000478

Prestwick1_000478

Prestwick2_000478

Prestwick3_000478

(.+/-.)-Felodipine

FELODIPINE [USAN]

FELODIPINE [VANDF]

F 9677

CHEMBL1480

FELODIPINE [WHO-DD]

Lopac0_000508

SCHEMBL26398

BSPBio_000616

AE-641/11429675

MLS001077361

MLS001333735

MLS002153409

MLS002153832

MLS003876820

BIDD:GT0733

SPBio_002555

BPBio1_000678

Felodipine (JP17/USP/INN)

Felodipine - Bio-X trade mark

GTPL4190

CHEMBL3196476

FELODIPINE [ORANGE BOOK]

SCHEMBL13460298

HY-B0309R

Felodipineextended-release Tablets

BDBM189379

HMS1569O18

HMS2089J05

HMS2096O18

HMS2232D24

HMS3259F12

HMS3261F17

HMS3651O21

HMS3713O18

HMS3884I14

Pharmakon1600-01505887

Felodipine Extended-release Tablets

BCP02192

BCP22685

HY-B0309

MSK10237

SYB74487

2,6-dimethyl-1,4-dihydropyridine-

Tox21_110155

Tox21_500508

CA-236

HB1222

NSC760343

s1885

FELODIPINE COMPONENT OF LEXXEL

AKOS015891545

Tox21_110155_1

AC-2124

BCP9000680

CCG-204599

DB01023

FF23238

KS-1264

LP00508

NC00721

SDCCGSBI-0050492.P002

O5-ethyl O3-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

NCGC00015455-04

NCGC00015455-05

NCGC00015455-06

NCGC00015455-07

NCGC00015455-08

NCGC00015455-10

NCGC00015455-24

NCGC00024087-02

NCGC00093906-01

NCGC00093906-02

NCGC00261193-01

4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

AC-24403

BF164445

Felodipine 100 microg/mL in Acetonitrile

PD002997

PD033051

SMR002529504

SY053174

DB-265041

3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-

EU-0100508

F0814

NS00002625

SW219299-1

EN300-70726

A10689

D00319

SBI-0050492.0001

Q420644

SR-01000075890-1

SR-01000075890-4

BRD-A30815329-001-03-0

BRD-A30815329-001-08-9

BRD-A30815329-001-10-5

Z239864852

Felodipine, European Pharmacopoeia (EP) Reference Standard

Felodipine, United States Pharmacopeia (USP) Reference Standard

3-ethyl5-methyl4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Ethyl methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

(.+/-.) Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

3,5-pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-ethyl-5-methylester

3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate #

3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate;Plendil

Solubility Characteristics of O5-ethyl O3-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Interesting Facts about O5-ethyl O3-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Solubility Characteristics of O₅-ethyl O₃-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Interesting Facts about O⁵-ethyl O³-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate