(S)-cetirizine

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

What is the (S)-cetirizine?

The molecule (S)-cetirizine presents a molecular formula of C21H25ClN2O3 and its IUPAC name is 2-[2-[4-[(S)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid.

Cetirizine is an antihistamine that is used to relieve allergy symptoms such as watery eyes, runny nose, itching eyes/nose, sneezing, hives, and itching. It works by blocking a certain natural substance (histamine) that your body makes during an allergic reaction..

Cetirizine exists as an over-the-counter (OTC) drug and as a prescription drug. The prescription form is used to treat chronic hives and itching associated with conditions such as eczema or psoriasis..

Cetirizine is also available in a combination product with the steroid medication, budesonide (Uceris). This product is used to treat ulcerative colitis..

Cetirizine may also be used for purposes not listed in this medication guide..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-cetirizine ZKLPARSLTMPFCP-NRFANRHFSA-N chemical compound 2D structure molecule svg
(S)-cetirizine

 

Molecule descriptors

 
IUPAC name2-[2-[4-[(S)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid
InChI codeInChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)/t21-/m0/s1
InChI KeyZKLPARSLTMPFCP-NRFANRHFSA-N
SMILESO=C(O)COCCN1CCN([C@@H](c2ccccc2)c2ccc(Cl)cc2)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.

  • (+)-cetirizine
  • (2-{4-[(S)-(4-Chlorophenyl)(Phenyl)methyl]piperazin-1-Yl}ethoxy)acetic Acid
  • (S)-(+)-DEXTROCETIRIZINE
  • (S)-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetic acid? (Cetirizine Impurity
  • (S)-cetirizine
  • (S)-dextrocetirizine
  • (s)cetirizine
  • 130018-76-7
  • 2-(2-(4-((S)-(4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic acid
  • 2-[2-[4-[(S)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid
  • Acetic acid, (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, (S)-
  • Acetic acid, (2-(4-((S)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-
  • Acetic acid, 2-(2-(4-((S)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-
  • BDBM85029
  • CS-0166224
  • CZE
  • Cetirizine (+) isomer
  • Cetirizine, (S)-
  • Dextrocetirizine
  • GTPL1215
  • NC00271
  • NCGC00016949-01
  • PDSP1_000532
  • PDSP2_000530
  • Q27459023
  • V57G6B5I8Z

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC19364229
  • CAS-83881-52-1
  • UNII-V57G6B5I8Z
  • AKOS015895045
  • CHEMBL1334217
  • SCHEMBL5526985

Physico-Chemical properties

IUPAC name2-[2-[4-[(S)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid
Molecular formulaC21H25ClN2O3
Molecular weight388.888
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity113.73
LogP3.0
Topological polar surface area53.0

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.