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Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl2O4
Molecular Weight 365.207
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDACRINONE

SMILES

CC1(CC2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C1=O)C3=CC=CC=C3

InChI

InChIKey=PRKWVSHZYDOZLP-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C18H14Cl2O4
Molecular Weight 365.207
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:52 UTC 2023
Edited
by admin
on Fri Dec 15 15:16:52 UTC 2023
Record UNII
B926Y9U4QN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDACRINONE
INN   USAN  
INN   USAN  
Official Name English
MK-196
Code English
ACETIC ACID, ((6,7-DICHLORO-2,3-DIHYDRO-2-METHYL-1-OXO-2-PHENYL-1H-INDEN-5-YL)OXY)-, (±)-
Common Name English
INDACRINONE [USAN]
Common Name English
ACETIC ACID, 2-((6,7-DICHLORO-2,3-DIHYDRO-2-METHYL-1-OXO-2-PHENYL-1H-INDEN-5-YL)OXY)-
Systematic Name English
indacrinone [INN]
Common Name English
(±)-((6,7-DICHLORO-2-METHYL-1-OXO-2-PHENYL-5-INDANYL)OXY)ACETIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C49184
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
Code System Code Type Description
INN
4650
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
WIKIPEDIA
Indacrinone
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
EVMPD
SUB08164MIG
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
NCI_THESAURUS
C80956
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
FDA UNII
B926Y9U4QN
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
259-965-3
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
PUBCHEM
42266
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
CAS
56049-88-8
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
MESH
C013352
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
CAS
57296-63-6
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
SUPERSEDED
SMS_ID
100000083367
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL7797
Created by admin on Fri Dec 15 15:16:52 UTC 2023 , Edited by admin on Fri Dec 15 15:16:52 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY