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Substance Name: Spironolactone [USP:INN:BAN:JAN]
RN: 52-01-7
UNII: 27O7W4T232
InChIKey: LXMSZDCAJNLERA-ZHYRCANASA-N
Note
- A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827).
Molecular Formula
- C24-H32-O4-S
Molecular Weight
- 416.5788
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Antiviral (COVID-19)
- Diuretic
- Diuretics
- Drug / Therapeutic Agent
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Human Data
- Laxative
- Mineralocorticoid Receptor Antagonists
- Natriuretic Agents
- Reproductive Effect
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms
Name of Substance
- Spironolactone
- Spironolactone [USP:INN:BAN:JAN]
MeSH Heading
- Spironolactone
Synonyms
- 17-Hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid, gamma-lactone acetate
- 17alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7alpha-mercapto-3-oxo-, gamma-lactone, acetate
- 3'-(3-Oxo-7-alpha-acetylthio-17-beta-hydroxyandrost-4-en-17-beta-yl)propionic acid lactone
- 3-(3-Keto-7-alpha-acetylthio-17-beta-hydroxy-4-androsten-17-alpha-yl)propionic acid lactone
- 4-18-00-01601 (Beilstein Handbook Reference)
- 7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone
- Acelat
- Aldace
- Aldactone
- Aldactone A
- Alderon
- Aldopur
- Almatol
- Altex
- Aquareduct
- Berlactone
- BRN 0057767
- Carospir
- Deverol
- Diatense
- Dira
- EINECS 200-133-6
- Espironolactona
- Espironolactona [INN-Spanish]
- Euteberol
- HSDB 3184
- Melarcon
- NSC 150399
- Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-
- SC 15983
- SC 9420
- Spiresis
- Spiridon
- Spiro(17H-cyclopenta(a)phenanthrene-17,2'(5'H)-furan), pregn-4-ene-21-carboxylic acid deriv.
- Spiro(17H-cyclopenta(a)phenauthrene-17,2'-(3'H)-furan)
- Spiro-Tablinen
- Spiroctan
- Spirolactone
- Spirolang
- Spirone
- Spironocompren
- Spironolactone
- Spironolactone A
- Spironolactonum
- Spironolactonum [INN-Latin]
- Spironolattone
- Spironolattone [DCIT]
- UNII-27O7W4T232
- Uractone
- Urusonin
- Verospiron
- Verospirone
- Xenalon
Systematic Names
- 17-alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7-alpha-mercapto-3-oxo-, gamma-lactone acetate
- 7-alpha-(acetylthio)-17-alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, gamma-lactone (9CI)
- Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-
- Spironolactone
Superlist Name
- Spironolactone
Mixture Name
- Aldactazide
Registry Numbers
CAS Registry Number
- 52-01-7
FDA UNII
- 27O7W4T232
Other Registry Numbers
- 1050678-93-7
- 1436392-20-9
- 496916-40-6
System Generated Number
- 0000052017
Structure Descriptors
InChI
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/s1InChIKey
LXMSZDCAJNLERA-ZHYRCANASA-NSmiles
CC(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 5600mg/kg (5600mg/kg) | Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972. | |
human | TDLo | oral | 5600mg/kg (5600mg/kg) | Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972. | |
human | TDLo | oral | 5600mg/kg (5600mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972. |
man | TDLo | oral | 5714ug/kg/4D- (5.714mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) BLOOD: AGRANULOCYTOSIS | Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 974, 1987. |
man | TDLo | oral | 7500ug/kg/3W- (7.5mg/kg) | BLOOD: AGRANULOCYTOSIS | Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000. |
man | TDLo | oral | 7500ug/kg/3W- (7.5mg/kg) | BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: AGRANULOCYTOSIS | Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000. |
mouse | LD50 | intraperitoneal | 260mg/kg (260mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
mouse | LD50 | intravenous | 260mg/kg (260mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
mouse | LD50 | oral | > 1gm/kg (1000mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rabbit | LD50 | intraperitoneal | 866mg/kg (866mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rabbit | LD50 | oral | > 1gm/kg (1000mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rat | LD50 | intraperitoneal | 277mg/kg (277mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
rat | LD50 | oral | > 1gm/kg (1000mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
women | TDLo | oral | 70mg/kg/5W-I (70mg/kg) | BLOOD: AGRANULOCYTOSIS | British Medical Journal. Vol. 289, Pg. 731, 1984. |
women | TDLo | oral | 122mg/kg/61D- (122mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | New Zealand Medical Journal. Vol. 83, Pg. 147, 1976. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 134.5 | deg C | EXP | |
log P (octanol-water) | 2.78 | (none) | EXP | |
Water Solubility | 22 | mg/L | 25 | EXP |
Vapor Pressure | 3.24E-11 | mm Hg | 25 | EST |
Henry's Law Constant | 1.14E-10 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.13E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.