Indacrinone

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Indacrinone
Identifiers
  • [(6,7-Dichloro-2-methyl-1-oxo-2-phenyl-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.054.496 Edit this at Wikidata
Chemical and physical data
FormulaC18H14Cl2O4
Molar mass365.21 g·mol−1
3D model (JSmol)
  • CC1(Cc2cc(c(c(c2C1=O)Cl)Cl)OCC(=O)O)c3ccccc3
  • InChI=1S/C18H14Cl2O4/c1-18(11-5-3-2-4-6-11)8-10-7-12(24-9-13(21)22)15(19)16(20)14(10)17(18)23/h2-7H,8-9H2,1H3,(H,21,22)
  • Key:PRKWVSHZYDOZLP-UHFFFAOYSA-N

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. ^ Vlasses PH, Rotmensch HH, Swanson BN, Irvin JD, Johnson CL, Ferguson RK (1984). "Indacrinone: natriuretic and uricosuric effects of various ratios of its enantiomers in healthy men". Pharmacotherapy. 4 (5): 272–7. doi:10.1002/j.1875-9114.1984.tb03374.x. PMID 6504708. S2CID 19743065.
  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. S2CID 36115871.
  3. ^ Kannappan, Valliappan. "Indacrinone – Chiralpedia". Retrieved 2022-08-28.
  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.{{cite book}}: CS1 maint: others (link)
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