(R)-Ketoprofen Acyl-beta-D-glucuronide

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

What is the (R)-Ketoprofen Acyl-beta-D-glucuronide?

The molecule (R)-Ketoprofen Acyl-beta-D-glucuronide presents a molecular formula of C22H22O9 and its IUPAC name is (2S,3S,4S,5R,6S)-6-[(2R)-2-(3-benzoylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

Ketoprofen is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is the active ingredient in a number of over-the-counter and prescription medications, including Orudis and Oruvail. Ketoprofen works by inhibiting the production of prostaglandins, which are hormones that play a role in pain and inflammation..

The ketoprofen molecule consists of a ketone group (represented by the "keto" in its name) attached to a propionic acid group. The ketone group makes ketoprofen a member of the class of drugs known as ketones. The propionic acid group gives ketoprofen its anti-inflammatory properties..

Ketoprofen is rapidly absorbed from the gastrointestinal tract and undergoes extensive first-pass metabolism in the liver. It is metabolized to its active metabolite, ketoprofen acyl-beta-D-glucuronide (KAG), which is then conjugated with glucuronic acid and excreted in the urine..

The half-life of ketoprofen is approximately 3 hours. Peak plasma concentrations of KAG are reached 2-3 hours after an oral dose..

Ketoprofen is generally well-tolerated, but side effects can include gastrointestinal upset, dizziness, and headache. Ketoprofen should be used with caution in patients with liver or kidney disease, as well as in those with a history of ulcers or gastrointestinal bleeding. It should also be used with caution in pregnant or nursing women..

Ketoprofen is a valuable addition to the pain reliever and anti-inflammatory arsenal. When used as directed, it is generally safe and effective..

3D structure

Cartesian coordinates

Geometry of (R)-Ketoprofen Acyl-beta-D-glucuronide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(R)-Ketoprofen Acyl-beta-D-glucuronide PBTXSZZKPHBHMA-IFMPTUIRSA-N chemical compound 2D structure molecule svg
(R)-Ketoprofen Acyl-beta-D-glucuronide

 

Molecule descriptors

 
IUPAC name(2S,3S,4S,5R,6S)-6-[(2R)-2-(3-benzoylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI codeInChI=1S/C22H22O9/c1-11(13-8-5-9-14(10-13)15(23)12-6-3-2-4-7-12)21(29)31-22-18(26)16(24)17(25)19(30-22)20(27)28/h2-11,16-19,22,24-26H,1H3,(H,27,28)/t11-,16+,17+,18-,19+,22+/m1/s1
InChI KeyPBTXSZZKPHBHMA-IFMPTUIRSA-N
SMILESC[C@@H](C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c1cccc(C(=O)c2ccccc2)c1

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.

  • (2S,3S,4S,5R,6S)-6-[(2R)-2-(3-benzoylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  • (R)-Ketoprofen Acyl-
  • (R)-Ketoprofen Acyl-beta-D-glucuronide
  • 140148-25-0
  • A-D-glucuronide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC31417974

Physico-Chemical properties

IUPAC name(2S,3S,4S,5R,6S)-6-[(2R)-2-(3-benzoylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC22H22O9
Molecular weight430.405
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity105.25
LogP0.5
Topological polar surface area150.6

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.