Spironolactone

A steroidal aldosterone antagonist used in the treatment of heart failure, hypertension, primary hyperaldosteronism, and edema associated with certain renal or hepatic disorders. Spironolactone competitively blocks mineralocorticoid receptors, increasing sodium and water excretion while reducing potassium loss. It also exhibits antiandrogenic activity and is used for selected androgen-related conditions, including hirsutism and acne. Its active metabolites, including canrenone, contribute to its prolonged pharmacological effects

CAS Number: 52-01-7

Molecular Mass: 416.6 g/mol

Formula: C₂₄H₃₂O₄S

Smiles: CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@@]34CCC(=O)O4)[C@H]12

Synonymes:

Spironolactone, spironolactone, 52-01-7, Aldactone, Verospirone, Spirolactone, Spiresis, Uractone, Xenalon, spironolattone, Espironolactona, Spironolactonum, Abbolactone, Diatensec, Laractone, SC 9420, SC-9420, Spironolactone ceva, Carospir, Spiretic, NSC-150399, DTXSID6034186, 27O7W4T232, CHEBI:9241, S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate, Veroshpiron, DTXCID4014186, SC9420, NSC150399, 3-(3-Keto-7-alpha-acetylthio-17-beta-hydroxy-4-androsten-17-alpha-yl)propionic acid lactone, 17alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7alpha-mercapto-3-oxo-, gamma-lactone, acetate, Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-, CARDALIS COMPONENT SPIRONOLACTONE, 7-alpha-(acetylthio)-17-alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, gamma-lactone, NovoSpiroton, Novo Spiroton, Spirono Isis, von ct, spiro, (1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan]-6'-ene-5,5'-dione, Gx spironol, Spirospare 25, Spiroctan 25, Spiroctan 50, Ct, Spiro Von, Spirospare 100, (1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro(oxolane-2,14'-tetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan)-6'-ene-5,5'-dione, S-((7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro(2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta(a)phenanthrene-17,2'-oxolane)-7-yl) ethanethioate, Spiroctan 100, RefChem:6256, C03DA01, 7alpha-Acetylsulfanyl-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone, (1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro(oxolane-2,14'-tetracyclo(8.7.0.02,7.011,15)heptadecan)-6'-ene-5,5'-dione, 17-Hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylic Acid, gamma Lactone, Acetate, 200-133-6, Euteberol, Spirolang, Verospiron, Spiroctan, Urusonin, Aldactone A, Spironocompren, Melarcon, Spiridon, Acelat, Alderon, Spirone, Dira, Spiro-Tablinen, Spironolactone A, Aldopur, Almatol, Aquareduct, Aldace, Deverol, Altex, Berlactone, MFCD00082250, C24H32O4S, CHEMBL1393, 17-Hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate, Spiro(17H-cyclopenta(a)phenauthrene-17,2'-(3'H)-furan), Spironolattone [DCIT], 17-Hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid, gamma-lactone acetate, SNL, Aldactide, Spironolactonum [INN-Latin], Espironolactona [INN-Spanish], SC 15983, Spiro[17H-cyclopenta[a]phenauthrene-17,2'-(3'H)-furan], Diatense, 7alpha-Acetylthio-3-oxo-17alpha-pregn-4-ene-21,17beta-carbolactone, Aldactone (TN), SMR000471892, HSDB 3184, EINECS 200-133-6, NSC 150399, BRN 0057767, spirotone, Spiranolactone, Qaialdo, UNII-27O7W4T232, Spironolactone RS, 2oax, 3vhu, CAS-52-01-7, Spironolactone CRS, NCGC00015948-02, 3-(3-Keto-7.alpha.-acetylthio-17.beta.-hydroxy-4-androsten-17.alpha.-yl)propionic acid lactone, 7-.alpha.-(acetylthio)-17-.alpha.-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, .gamma.-lactone, 7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone, Spironolactone [USP:INN:BAN:JAN], Prestwick0_000128, Prestwick1_000128, Prestwick2_000128, Prestwick3_000128, SC 9420, Aldactone, Spironolactone (Standard), SPIRONOLACTONE [MI], 3'-(3-Oxo-7-alpha-acetylthio-17-beta-hydroxyandrost-4-en-17-beta-yl)propionic acid lactone, SPIRONOLACTONE [INN], SPIRONOLACTONE [JAN], BIDD:PXR0071, SCHEMBL20939, BSPBio_000176, SPIRONOLACTONE [HSDB], SPIRONOLACTONE [IARC], 4-18-00-01601 (Beilstein Handbook Reference), MLS001074672, MLS001333253, MLS001333254, MLS002153245, MLS002207058, MLS002548846, SPIRONOLACTONE [VANDF], SPBio_002115, SPIRONOLACTONE [MART.], BPBio1_000194, GTPL2875, orb1310575, SPIRONOLACTONE [USP-RS], SPIRONOLACTONE [WHO-DD], SPIRONOLACTONE [WHO-IP], HY-B0561R, Spironolactone (JP18/USP/INN), GLXC-10093, HMS1568I18, HMS2090N21, HMS2095I18, HMS2236E06, HMS3259G11, HMS3712I18, Spironolactone - Bio-X trade mark, HY-B0561, Spironolactone, 97.0-103.0%, SPIRONOLACTONE [ORANGE BOOK], Tox21_113047, Tox21_302154, 7alpha-(acetylsulfanyl)-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone, BDBM50228080, EBC-09098, HB2799, MSK000578, s4054, SPIRONOLACTONE [EP MONOGRAPH], SPIRONOLACTONE [USP MONOGRAPH], AKOS015896401, SPIRONOLACTONUM [WHO-IP LATIN], AC-4214, CCG-220128, DB00421, FS15791, KS-5234, NC00482, SPIRONOLACTONE COMPONENT CARDALIS, NCGC00015948-10, NCGC00164397-01, NCGC00164397-02, NCGC00164397-03, NCGC00164397-05, NCGC00255229-01, (1R,3aS,3bR,4R,9aR,9bS,11aS)-4-(acetylsulfanyl)-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione, 17-alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7-alpha-mercapto-3-oxo-, gamma-lactone acetate, BS166385, CPD000471892, Spironolactone 1.0 mg/ml in Acetonitrile, Spironolactone for system suitability CRS, ALDACTAZIDE COMPONENT SPIRONOLACTONE, SPIRONOLACTONE [EMA EPAR VETERINARY], AB00513806, NS00000424, S0260, C07310, C75438, D00443, EN300-123035, AB01275520-01, AB01275520_02, Q422188, SR-01000765419, SR-05000000452, SR-01000765419-2, SR-05000000452-2, BRD-K90027355-001-03-4, BRD-K90027355-001-13-3, BRD-K90027355-001-19-0, Z1546616196, Spironolactone, European Pharmacopoeia (EP) Reference Standard, WLN: L E5 B666 FX OV MUTJ A1 E1 KSV1 F-& CT5VOXTJ, 17.alpha.-Pregn-4-ene-21-carboxylic acid, .gamma.-lactone acetate, Spironolactone, United States Pharmacopeia (USP) Reference Standard, 17.alpha.-Pregn-4-ene-21-carboxylic acid, .gamma.-lactone, acetate, Pregn-4-ene-21-carboxylic acid, .gamma.-lactone, (7.alpha.,17.alpha.)-, Spironolactone for system suitability, European Pharmacopoeia (EP) Reference Standard, 2'',15''-dimethyl-5,5''-dioxo-(9''R)-spiro[tetrahydrofuran-2,14''-tetracyclo[8.7.0.02,7.011,15]heptadec-6''-ene]-9-yl ethanethioate, 2'',15''-dimethyl-5,5''-dioxospiro[tetrahydrofuran-2,14''-tetracyclo[8.7.0.02,7.011,15]heptadec-6''-ene]-9-yl ethanethioate, 2'',15''-dimethyl-5,5''-dioxospiro[tetrahydrofuran-2,14''-tetracyclo[8.7.0.02,7.011,15]heptadec-6''-ene]-9-yl ethanethioate(Spiranolactone), PREGN-4-ENE-21-CARBOXYLIC ACID, 7-(ACETYLTHIO)-17-HYDROXY-3-OXO-,.GAMMA.-LACTONE, (7.ALPHA.,17.ALPHA.)-, S-((2'R,7R,8R,9S,10R,13S,14S)-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl) ethanethioate, S-(2''R,7R,8R,9S,10R,13S,14S)-10,13-dimethyl-3,5''-dioxo-1,2,3,4'',5'',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3''H-spiro[cyclopenta[a]phenanthrene-17,2''-furan]-7-yl ethanethioate, S-[(1R,3aS,3bR,4R,9aR,9bS,11aS)-9a,11a-Dimethyl-5',7-dioxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolan]-4-yl] ethanethioate, S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl] ethanethioate, S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxo-spiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-tetrahydrofuran]-7-yl] ethanethioate

Bioactivity: Mineralocorticoid receptor antagonist; potassium-sparing diuretic; antiandrogen

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.95	-	8.95	[86]
1-Butanol	283.65	-	10.89	[86]
1-Butanol	288.55	-	14.18	[86]
1-Butanol	293.45	-	18.06	[86]
1-Butanol	298.25	-	21.35	[86]
1-Butanol	303.05	-	26.35	[86]
1-Butanol	308.15	-	33.1	[86]
1-Butanol	312.95	-	40.46	[86]
1-Butanol	317.65	-	49.63	[86]
1-Propanol	278.4	-	12.92	[86]
1-Propanol	283.65	-	14.68	[86]
1-Propanol	288.35	-	18.28	[86]
1-Propanol	293.25	-	22.11	[86]
1-Propanol	298.15	-	27.2	[86]
1-Propanol	303.05	-	33.61	[86]
1-Propanol	307.95	-	41.79	[86]
1-Propanol	312.9	-	52.73	[86]
1-Propanol	318.35	-	66.27	[86]
Ethanol	278.75	-	12.35	[86]
Ethanol	283.55	-	14.21	[86]
Ethanol	288.45	-	17.11	[86]
Ethanol	293.45	-	22.21	[86]
Ethanol	298.35	-	28.09	[86]
Ethanol	303.15	-	34.81	[86]
Ethanol	308.25	-	42.81	[86]
Ethanol	313.15	-	54.22	[86]
Ethanol	317.95	-	68.36	[86]
Ethyl acetate	278.85	-	79.31	[86]
Ethyl acetate	283.65	-	87.04	[86]
Ethyl acetate	288.55	-	98.85	[86]
Ethyl acetate	293.45	-	107.4	[86]
Ethyl acetate	298.3	-	122.3	[86]
Ethyl acetate	303.15	-	136.0	[86]
Ethyl acetate	308.1	-	155.3	[86]
Ethyl acetate	312.95	-	178.1	[86]
Ethyl acetate	317.75	-	196.5	[86]
Isopropanol	278.45	-	5.51	[86]
Isopropanol	283.55	-	7.076	[86]
Isopropanol	288.4	-	9.196	[86]
Isopropanol	293.25	-	11.33	[86]
Isopropanol	298.2	-	14.4	[86]
Isopropanol	303.05	-	18.55	[86]
Isopropanol	307.95	-	23.94	[86]
Isopropanol	312.9	-	30.65	[86]
Isopropanol	317.55	-	39.03	[86]
Methanol	278.85	-	2.115	[86]
Methanol	283.65	-	2.781	[86]
Methanol	288.55	-	3.68	[86]
Methanol	293.45	-	4.22	[86]
Methanol	298.3	-	6.258	[86]
Methanol	303.15	-	8.27	[86]
Methanol	308.1	-	10.48	[86]
Methanol	312.95	-	13.97	[86]
Methanol	317.75	-	18.22	[86]

Molecule 3D descriptors

Descriptor	Value
PMI1	1900.5765
PMI2	5260.7027
PMI3	6442.5652
NPR1	0.2950
NPR2	0.8166
RadiusOfGyration	4.0408
InertialShapeFactor	0.0004
Eccentricity	0.9555
Asphericity	0.3601
SpherocityIndex	0.2985
PBF	1.0946