(S)-Venlafaxine

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

What is the (S)-Venlafaxine?

The molecule (S)-Venlafaxine presents a molecular formula of C₁₇H₂₇NO₂ and its IUPAC name is 1-[(1S)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol.

Venlafaxine is a serotonin and norepinephrine reuptake inhibitor (SNRI) antidepressant. It is used to treat major depressive disorder (MDD), anxiety, and panic disorder. .

The chemical structure of venlafaxine is a phenethylamine derivative. The molecule consists of a phenyl ring and an ethyl amine group. The phenyl ring is substituted with a nitrogen atom and two chlorine atoms. The ethyl amine group is attached to the phenyl ring at the 2-position. .

Venlafaxine is a white to off-white powder that is slightly soluble in water. The primary mechanism of action of venlafaxine considered to be inhibition of the reuptake of serotonin and norepinephrine in the central nervous system..

In preclinical studies, venlafaxine was found to increase serotonin and norepinephrine activity in the brain. These increases were associated with antidepressant, anxiolytic, and anti-panic effects in animal models..

Venlafaxine has a half-life of about 4 to 6 hours. It is metabolized in the liver by the cytochrome P450 system. The primary metabolites are O-desmethylvenlafaxine and N-desvenlafaxine. Both of these metabolites are pharmacologically active..

Venlafaxine is well absorbed from the gastrointestinal tract. It is extensively metabolized in the liver and only about 1% of the parent compound is excreted in the urine..

The most common side effects of venlafaxine are nausea, vomiting, dry mouth, constipation, diarrhea, sweating, and dizziness. Less common side effects include increased heart rate, tremor, and anxiety..

Venlafaxine should not be used in patients with a history of seizure disorder or mania. It should be used with caution in patients with a history of cardiovascular disease or hypertension..

Venlafaxine lies as a pregnancy category C drug. There are no adequate and well-controlled studies in pregnant women. Venlafaxine should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus..

Nursing mothers should not breastfeed while taking venlafaxine..

3D structure

Cartesian coordinates

Geometry of (S)-Venlafaxine 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.