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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O4S
Molecular Weight 416.573
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPIRONOLACTONE

SMILES

[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]4([H])[C@@]2([H])[C@@H](CC5=CC(=O)CC[C@]45C)SC(C)=O

InChI

InChIKey=LXMSZDCAJNLERA-ZHYRCANASA-N
InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1

HIDE SMILES / InChI
Molecular Formula C24H32O4S
Molecular Weight 416.573
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:56:14 UTC 2023
Edited
by admin
on Sat Dec 16 16:56:14 UTC 2023
Record UNII
27O7W4T232
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SPIRONOLACTONE
EP   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
SPIRONOLACTONE [MART.]
Common Name English
VEROSPIRONE
Common Name English
SPIRONOLACTONE [INCI]
Common Name English
17-Hydroxy-7α-mercapto-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone acetate
Common Name English
SPIRONOLACTONE CEVA
Brand Name English
SPIRONOLACTONE [IARC]
Common Name English
ALDACTONE
Brand Name English
SPIRONOLACTONUM [WHO-IP LATIN]
Common Name English
Spironolactone [WHO-DD]
Common Name English
SPIRONOLACTONE [JAN]
Common Name English
SPIRONOLACTONE COMPONENT CARDALIS
Common Name English
SPIRONOLACTONE [USP MONOGRAPH]
Common Name English
SPIRONOLACTONE [WHO-IP]
Common Name English
NSC-150399
Code English
CARDALIS COMPONENT SPIRONOLACTONE
Brand Name English
SPIRONOLACTONE [ORANGE BOOK]
Common Name English
SPIRONOLACTONE [USP-RS]
Common Name English
spironolactone [INN]
Common Name English
SPIRONOLACTONE [MI]
Common Name English
SPIRONOLACTONE [EMA EPAR VETERINARY]
Common Name English
SPIRONOLACTONE [VANDF]
Common Name English
SPIRONOLACTONE COMPONENT OF ALDACTAZIDE
Common Name English
PREGN-4-ENE-21-CARBOXYLIC ACID, 7-(ACETYLTHIO)-17-HYDROXY-3-OXO-,.GAMMA.-LACTONE, (7.ALPHA.,17.ALPHA.)-
Common Name English
ALDACTAZIDE COMPONENT SPIRONOLACTONE
Common Name English
SPIRONOLACTONE [HSDB]
Common Name English
SC-9420
Code English
SPIRONOLACTONE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 16
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS SPIRONOLACTONE CEVA [AUTHORIZED]
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
NDF-RT N0000011310
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
FDA ORPHAN DRUG 430614
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
IARC Spironolactone
LIVERTOX NBK547921
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
NCI_THESAURUS C49186
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
WHO-ATC C03DA01
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
NDF-RT N0000175557
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS CARDALIS (AUTHORISED)
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
WHO-VATC QC03DA01
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2475
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
DAILYMED
27O7W4T232
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID6034186
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
RS_ITEM_NUM
1619006
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
CAS
52-01-7
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
DRUG BANK
DB00421
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
WIKIPEDIA
SPIRONOLACTONE
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
LACTMED
Spironolactone
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
SMS_ID
100000092408
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
NCI_THESAURUS
C840
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
PUBCHEM
5833
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
HSDB
3184
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
EVMPD
SUB127260
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
ALTERNATIVE
INN
987
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
MESH
D013148
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
CHEBI
9241
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SPIRONOLACTONE
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY Description: A light yellowish white to light yellowish brown powder; odourless or with a faint characteristic odour. Solubility: Practically insoluble in water; soluble in ethanol (~750 g/l) TS. Category: Diuretic. Storage: Spironolactone should be kept in a well-closed container, protected from light. Additional information: Spironolactone may show preliminary melting at about 135?C, followed by resolidification. Definition: Spironolactone contains not less than 97.0% and not more than 101.5% of C24H32O4S, calculated with reference to the dried substance.
EVMPD
SUB10631MIG
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
ChEMBL
CHEMBL1393
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
IUPHAR
2875
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
NSC
150399
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-133-6
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
FDA UNII
27O7W4T232
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY
MERCK INDEX
m10157
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY Merck Index
RXCUI
9997
Created by admin on Sat Dec 16 16:56:16 UTC 2023 , Edited by admin on Sat Dec 16 16:56:16 UTC 2023
PRIMARY RxNorm
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
ANDROGEN RECEPTOR
TARGET->PARTIAL ANTAGONIST
BINDING
MINERALOCORTICOID RECEPTOR
TARGET -> INHIBITOR
Is a prodrug that Inhibits through active metabolites.
Related Record Type Details
Structure of CANRENONE
METABOLITE ACTIVE -> PRODRUG
Structure of 7.ALPHA.-THIOMETHYLSPIRONOLACTONE
METABOLITE ACTIVE -> PRODRUG
MAJOR
PLASMA
Structure of 6.BETA.-HYDROXY-7.ALPHA.-THIOMETHYLSPIROLACTONE
METABOLITE -> PARENT
Structure of 6.BETA.-HYDROXY-7.ALPHA.-THIOMETHYLSPIROLACTONE
METABOLITE ACTIVE -> PRODRUG
The pharmacological activity of spironolactone metabolites in man is not known. However, in the adrenalectomized rat the antimineralocorticoid activities of the metabolites C, TMS, and HTMS, relative to spironolactone, were 1.10, 1.28, and 0.32, respectively.
Structure of 7.ALPHA.-THIOMETHYLSPIRONOLACTONE
METABOLITE ACTIVE -> PRODRUG
Has in vitro activity
Structure of DEACETYLSPIRONOLACTONE
METABOLITE ACTIVE -> PARENT
Structure of DEACETYLSPIRONOLACTONE
METABOLITE -> PARENT
Related Record Type Details
Structure of (2'R)-7ALPHA-(ACETYLTHIO)-5'H-SPIRO(ANDROST-4-ENE-17,2'-FURAN)-3,5'-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 6.BETA.-HYDROXY-SPIRONOLACTONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2R)-3,4-DIHYDRO-5H-SPIRO(ANDROST-4-ENE-17,2-FURAN)-3,5-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2S)-SPIRO(ANDROST-4,6-DIENE-17,2-OXIRAN)-3-ONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Disulfanyl-spironolactone
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 17.ALPHA.-PREGN-4-ENE-21-CARBOXYLIC ACID, 17-HYDROXY-7.BETA.-MERCAPTO-3-OXO-, .GAMMA.-LACTONE, ACETATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of S-(17.ALPHA.-(ETHOXYMETHYL)-17.BETA.-HYDROXY-3-OXOANDROST-4-EN-7.ALPHA.-YL) ETHANETHIOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CANRENONE
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity F by 2.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of SPIRONOLACTONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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