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Details

Stereochemistry RACEMIC
Molecular Formula C18H13Cl2O4.Na
Molecular Weight 387.189
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDACRINONE SODIUM

SMILES

[Na+].CC1(CC2=CC(OCC([O-])=O)=C(Cl)C(Cl)=C2C1=O)C3=CC=CC=C3

InChI

InChIKey=CETPSHNEDKOTIY-UHFFFAOYSA-M
InChI=1S/C18H14Cl2O4.Na/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);/q;+1/p-1

HIDE SMILES / InChI
Indacrinone is an orally active, indanone-based loop diuretic patented by American pharmaceutical company Merck and Co as mixture of two enantiomers. In healthy volunteers, the racernic mixture of indacrinone exhibited greater natriuretic potency than furosemide, with a slower onset and longer duration of action. Furthermore, single doses of indacrinone decreased serum uric acid concentrations and increased uric acid clearance, while similar doses of furosemide generally had the opposite effects. Differences in the pharmacologic effects of the resolved enantiomers of indacrinone were initially studied in animals and confirmed in a series of studies we conducted in healthy human volunteer. The S( + ) form is a potent uricosuric agent that produces mild natriuresis only at higher doses, while the R( - ) form is a potent loop diuretic with only transient uricosuric effects. The (-) enantiomer and its active metabolite appear to be primarily responsible for the natriuretic effects of the racemic mixture; the ( + ) enantiomer is 20-40 times less potent a natriuretic agent.

Approval Year

PubMed

PubMed

TitleDatePubMed
Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors.
2005 Jun 2
Patents

Patents

Sample Use Guides

10 mg
Route of Administration: Oral
Name Type Language
INDACRINONE SODIUM
Common Name English
ACETIC ACID, ((6,7-DICHLORO-2,3-DIHYDRO-2-METHYL-1-OXO-2-PHENYL-1H-INDEN-5-YL)OXY)-, SODIUM SALT
Common Name English
ACETIC ACID, 2-((6,7-DICHLORO-2,3-DIHYDRO-2-METHYL-1-OXO-2-PHENYL-1H-INDEN-5-YL)OXY)-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
CAS
67938-94-7
Created by admin on Sat Dec 16 11:55:22 GMT 2023 , Edited by admin on Sat Dec 16 11:55:22 GMT 2023
SUPERSEDED
FDA UNII
AUS78544YM
Created by admin on Sat Dec 16 11:55:22 GMT 2023 , Edited by admin on Sat Dec 16 11:55:22 GMT 2023
PRIMARY
CAS
76698-88-9
Created by admin on Sat Dec 16 11:55:22 GMT 2023 , Edited by admin on Sat Dec 16 11:55:22 GMT 2023
PRIMARY
PUBCHEM
86735780
Created by admin on Sat Dec 16 11:55:22 GMT 2023 , Edited by admin on Sat Dec 16 11:55:22 GMT 2023
PRIMARY