Dapiprazole

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

What is the Dapiprazole?

The molecule Dapiprazole presents a molecular formula of C19H27N5 and its IUPAC name is 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine.

Dapiprazole (marketed as Hydroxyzine Hydrochloride in the US) is a second-generation antihistamine of the diphenylmethylpiperazine class. It has anticholinergic, sedative, and antiemetic properties and is used for the treatment of anxiety, insomnia, nausea, and vomiting. It was first synthesized in the 1960s and was approved for use in the United States in 1986..

Dapiprazole has a high affinity for histamine H1 receptors and a moderate affinity for muscarinic acetylcholine receptors. It is a potent antagonist of both receptors with a binding affinity that is approximately 300 times that of histamine for the H1 receptor and 50 times that of acetylcholine for the muscarinic receptor. The clinical effects of dapiprazole are mediated by its binding to these receptors in the brain..

Dapiprazole is well absorbed from the gastrointestinal tract and has an elimination half-life of 12-24 hours. It is metabolized in the liver by cytochrome P450 enzymes and excreted in the urine..

Dapiprazole is indicated for the treatment of anxiety, insomnia, nausea, and vomiting. It is also used as an adjunct to other agents for the treatment of motion sickness..

The most common side effects of dapiprazole are dry mouth, drowsiness, and dizziness. Other less common side effects include constipation, diarrhea, headache, and fatigue..

Dapiprazole is contraindicated in patients with a history of hypersensitivity to the drug..

3D structure

Cartesian coordinates

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

2D drawing

 

Dapiprazole RFWZESUMWJKKRN-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Dapiprazole

 

Molecule descriptors

 
IUPAC name3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
InChI codeInChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3
InChI KeyRFWZESUMWJKKRN-UHFFFAOYSA-N
SMILESCc1ccccc1N1CCN(CCc2nnc3n2CCCC3)CC1

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.

  • 1,2,4-Triazolo(4,3-a)pyridine, 5,6,7,8-tetrahydro-3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-
  • 1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine
  • 3-(2-(4-(o-Tolyl)piperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
  • 3-(2-(4-o-tolylpiperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
  • 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
  • 3-{2-[4-(2-methylphenyl)piperazin-1-yl]ethyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
  • 5,6,7,8-TETRAHYDRO-3-(2-(4-O-TOLYL-1-PIPERAZINYL)ETHYL))-S-TRIAZOLO(4,3-A)PYRIDINE
  • 5,6,7,8-Tetrahydro-3-(2-(4-(o-tolyl)-1-piperazinyl)ethyl)-s-triazolo(4,3-a)pyridine
  • 5RNZ8GJO7K
  • 72822-12-9
  • 72822-12-9 (free base)
  • 822D129
  • CS-0017462
  • D07775
  • DB-055682
  • DB00298
  • Dapiprazol
  • Dapiprazole
  • Dapiprazole (INN)
  • Dapirazol
  • Dapirazolum
  • FT-0603131
  • GTPL7155
  • Glamidolo
  • HY-A0142
  • L000681
  • NCGC00262927-03
  • Q901963
  • Remydrial
  • Reversil
  • dapiprazolum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1246
  • UNII-5RNZ8GJO7K
  • AKOS024463973
  • DTXSID90223140
  • CHEMBL1201216
  • CHEBI:51066
  • SCHEMBL152543

Physico-Chemical properties

IUPAC name3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
Molecular formulaC19H27N5
Molecular weight325.451
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity104.27
LogP2.3
Topological polar surface area37.2

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.