(S)-Nisoldipine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (S)-Nisoldipine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (S)-Nisoldipine?

The molecule (S)-Nisoldipine presents a molecular formula of C20H24N2O6 and its IUPAC name is 3-O-methyl 5-O-(2-methylpropyl) (4S)-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

S-Nisoldipine is a molecule that belongs to the class of drugs known as calcium channel blockers. It is used to treat hypertension (high blood pressure) and angina (chest pain)..

S-Nisoldipine works by blocking the calcium channels in the smooth muscle cells of the blood vessels, which results in the relaxation of the blood vessels and the lowering of blood pressure. It also decreases the heart rate and the amount of blood that the heart pumps..

S-Nisoldipine exists as an oral tablet and an oral solution. The oral tablet is usually taken two or three times a day. The oral solution is usually taken once a day..

Common side effects of S-Nisoldipine include headache, dizziness, and fatigue. S-Nisoldipine can also cause an increase in the level of potassium in the blood, which can lead to serious side effects such as irregular heartbeat and muscle weakness..

S-Nisoldipine should not be used in patients with severe kidney disease or in those who are taking certain other medications that can interact with S-Nisoldipine..

3D structure

Cartesian coordinates

Geometry of (S)-Nisoldipine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(S)-Nisoldipine VKQFCGNPDRICFG-SFHVURJKSA-N chemical compound 2D structure molecule svg
(S)-Nisoldipine

 

Molecule descriptors

 
IUPAC name3-O-methyl 5-O-(2-methylpropyl) (4S)-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
InChI codeInChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3/t18-/m0/s1
InChI KeyVKQFCGNPDRICFG-SFHVURJKSA-N
SMILESCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)[C@H]1c1ccccc1[N+](=O)[O-]

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-(S)-methyl 2-methylpropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
  • (+)-(S)-nisoldipine
  • (+)-methyl 2-methylpropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
  • (+)-nisoldipine
  • (S)-(+)-methyl 2-methylpropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
  • (S)-(+)-nisoldipine
  • (S)-Nisoldipine
  • 103573-38-2
  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, 3-methyl 5-(2-methylpropyl) ester, (4S)-
  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, methyl 2-methylpropyl ester, (4S)-
  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, methyl 2-methylpropyl ester, (S)-
  • Nisoldipine, (S)-
  • Q27146426
  • Z8QN466QKA
  • methyl 2-methylpropyl (4S)-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC591993
  • UNII-Z8QN466QKA
  • CHEBI:76919

Physico-Chemical properties

IUPAC name3-O-methyl 5-O-(2-methylpropyl) (4S)-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Molecular formulaC20H24N2O6
Molecular weight388.414
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity108.95
LogP4.1
Topological polar surface area110.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.