Esmirtazapine

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

What is the Esmirtazapine?

The molecule Esmirtazapine presents a molecular formula of C17H19N3 and its IUPAC name is (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene.

Esmirtazapine (brand name: Remeron) is an antidepressant medication that belongs to a group of drugs called atypical antidepressants. It is used to treat major depressive disorder (MDD). Esmirtazapine is thought to work by increasing levels of norepinephrine and serotonin in the brain. These are two of the chemicals that are thought to be involved in the development of depression..

Esmirtazapine was first approved by the FDA in 2004. It exists as a generic drug and is manufactured by several different companies..

The most common side effects of esmirtazapine include weight gain, drowsiness, and dizziness. Other side effects include dry mouth, constipation, and increased appetite. Esmirtazapine may also cause increased blood pressure and heart rate..

Esmirtazapine should not be taken with monoamine oxidase inhibitors (MAOIs) or with other antidepressants. Taking esmirtazapine with MAOIs can cause a dangerous increase in blood pressure. Esmirtazapine should also not be taken with alcohol or with drugs that make you drowsy..

If you are taking esmirtazapine, it is important to tell your doctor if you are pregnant or planning to become pregnant. Esmirtazapine is a category C pregnancy drug, which means it may be harmful to a developing baby..

Esmirtazapine exists as a tablet and an orally disintegrating tablet. It is usually taken once a day, at bedtime..

3D structure

Cartesian coordinates

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

2D drawing

 

Esmirtazapine RONZAEMNMFQXRA-MRXNPFEDSA-N chemical compound 2D structure molecule svg
Esmirtazapine

 

Molecule descriptors

 
IUPAC name(7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
InChI codeInChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3/t16-/m1/s1
InChI KeyRONZAEMNMFQXRA-MRXNPFEDSA-N
SMILESCN1CCN2c3ncccc3Cc3ccccc3[C@H]2C1

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.

  • (+)-Mirtazapine
  • (14BS)-1,2,3,4,10,14B-HEXAHYDRO-2-METHYLPYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE
  • (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
  • (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.0?,?.0?,??]nonadeca-1(15),8,10,12,16,18-hexaene
  • (S)-1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
  • (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
  • (S)-Mirtazapine
  • (s)-6-azamianserin
  • (s)-org 3770
  • 4685R51V7M
  • 61337-87-9
  • BIDD:PXR0200
  • CS-0086936
  • DB06678
  • Esmirtazapine
  • HY-B0352A
  • Mirtazapine, (s)-
  • Org 44-20
  • Org-44-20
  • PDSP1_001530
  • PDSP2_001514
  • PYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-, (14BS)-
  • Q3058085
  • S-(+)-MIRTAZAPINE
  • S-Mirtazapine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC968310
  • UNII-4685R51V7M
  • DTXSID001029320
  • CHEMBL1366933
  • EINECS 262-714-0
  • SCHEMBL49330

Physico-Chemical properties

IUPAC name(7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
Molecular formulaC17H19N3
Molecular weight265.353
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity88.00
LogP2.5
Topological polar surface area19.4

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.