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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
 

Classification Codes

Classification Codes

  • Diuretic
  • Diuretics
  • Diuretics, Potassium Sparing
  • 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

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/s1

InChIKey

LXMSZDCAJNLERA-ZHYRCANASA-N

Smiles

CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]45CCC(=O)O5)[C@H]13

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.