Chemistry:Indacrinone

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Short description: Chemical compound
Indacrinone
Indacrinone.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H14Cl2O4
Molar mass365.21 g·mol−1
3D model (JSmol)

Indacrinone is a loop diuretic. It can be used in patients of gout with hypertension as an antihypertensive because it decreases reabsorption of uric acid,[1] while other diuretics increase it.

Chirality and biological activity

Indacrinone enantiomeric pair exhibiting therapeutic advantage
Indacrinone - Chiral twins

Indacrinone is a chiral drug, with one chiral center and hence exists as mirror-image twins. (R)-enantiomer, the eutomer, is diuretic whereas the mirror-image version (S)-enantiomer counteracts side effect of the eutomer. Here both the enantiomers contribute to the overall desired effect in different ways.

As indicated earlier, the (R)- enantiomer is the pharmacologically active diuretic. Like most other diuretics, the (R)-isomer possesses an undesirable side-effect of retaining uric acid. But the (S)-enantiomer, the distomer, has the property of assisting uric acid secretion (uricosuric effect), and, therefore, antagonizing the undesirable side-effects of the eutomer (uric-acid retention).[2][3] It affords a good argument for the marketing of a racemic mixture. But studies exemplify that 9:1 mixture of the two enantiomers provides optimal therapeutic value.[4]

See also

References

  1. "Indacrinone: natriuretic and uricosuric effects of various ratios of its enantiomers in healthy men". Pharmacotherapy 4 (5): 272–7. 1984. doi:10.1002/j.1875-9114.1984.tb03374.x. PMID 6504708. 
  2. Ariëns, Everardus J. (1986). "Stereochemistry: A source of problems in medicinal chemistry". Medicinal Research Reviews 6 (4): 451–466. doi:10.1002/med.2610060404. ISSN 0198-6325. PMID 3534485. http://dx.doi.org/10.1002/med.2610060404. 
  3. Kannappan, Valliappan. "Indacrinone – Chiralpedia" (in en-US). https://chiralpedia.com/blog/indacrinone/. 
  4. The impact of stereochemistry on drug development and use. Hassan Y. Aboul-Enein, Irving W. Wainer. New York: Wiley. 1997. ISBN 0-471-59644-2. OCLC 35262289. https://www.worldcat.org/oclc/35262289.