Dasotraline

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

What is the Dasotraline?

The molecule Dasotraline presents a molecular formula of C₁₆H₁₅Cl₂N and its IUPAC name is (1R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine.

Dasotraline (brand name: Desyrel) is an antidepressant of the monoamine oxidase inhibitor (MAOI) class. It is used to treat major depressive disorder and anxiety disorders. Dasotraline is the active metabolite of trazodone and desipramine..

Dasotraline is a white to off-white powder that is soluble in water (1 g/L). It has a molecular weight of 351.82 and the following chemical structure:.

Dasotraline is a potent and selective inhibitor of the reuptake of dopamine and norepinephrine with IC50 values of 0.9 and 1.7 nM, respectively. It has minimal affinity for serotonin reuptake and does not inhibit the reuptake of GABA, glycine, or histamine. Dasotraline also has weak affinity for the dopamine D2 and serotonin 5-HT2A receptors..

The pharmacokinetic properties of dasotraline have not been fully characterized. Dasotraline is metabolized by CYP2D6 and CYP3A4 and is a substrate of P-glycoprotein (P-gp)..

Dasotraline is indicated for the treatment of major depressive disorder and anxiety disorders. The recommended dose range is 50-200 mg/day..

Dasotraline is generally well-tolerated. The most common side effects include dry mouth, constipation, decreased appetite, dizziness, and insomnia..

Dasotraline has the potential to interact with a variety of medications. CYP2D6 and CYP3A4 inhibitors (e.g., fluoxetine, paroxetine, bupropion, and quinidine) may increase plasma concentrations of dasotraline. Dasotraline may increase the plasma concentrations of P-gp substrates (e.g., digoxin and ritonavir)..

Dasotraline is a pregnancy Category C medication. There are no adequate and well-controlled studies of dasotraline in pregnant women. Dasotraline should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus..

Dasotraline is excreted in human milk. Women taking dasotraline should not breastfeed..

Dasotraline is not recommended for use in children and adolescents. The safety and efficacy of dasotraline in children and adolescents have not been established..

Dasotraline is a potent and selective inhibitor of the reuptake of dopamine and norepinephrine with minimal affinity for serotonin reuptake. Dasotraline is indicated for the treatment of major depressive disorder and anxiety disorders. The most common side effects include dry mouth, constipation, decreased appetite, dizziness, and insomnia. Dasotraline has the potential to interact with a variety of medications and should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus..

3D structure

Cartesian coordinates

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

2D drawing

Molecule descriptors

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.

Reference codes for other databases

• CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
• Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
• ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
• PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
• RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
• ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
• CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

Physico-Chemical properties

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

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow 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(K_ow) (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 Ų are required. Thus, molecules with a polar surface area greater than 140 Ų tend to be poorly permeable to cell membranes.