spironolactone

General Material Information

Preferred name	spironolactone
Trivial Name	Spironolactone
Short Description	17-hydroxy-7a-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone acetate
Formula	C24 H32 O4 S
CAS Number	52-01-7
Deleted CAS Number	1050678-93-7
ECHA Number	200-133-6
FDA UNII	27O7W4T232
Nikkaji Number	J4.474A
Beilstein Number	0057767
MDL	MFCD00082250
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	abbolactone 3'-(3-oxo-7-alpha- acetyl thio-17-beta-hydroxyandrost-4-en-17-beta-yl) propionic acid lactone 7-alpha- acetyl thio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone 3-(3-oxo-7a- acetylthio-17b-hydroxy-4-androsten-17a-yl)propionic acid g-lactone (7a,17a)-7-( acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone aldace aldactide aldactone aldopur almatol aquareduct deverol diatensec 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 duraspiron euteberol 17-hydroxy-7a-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone acetate 17-hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid gamma-lactone acetate lacalmin lacdene laractone melarcon nefurofan osiren sagisal sincomen spiretic spiridon spiroctanie spiroderm spirolakton spirolone sprioderm supra-puren uractone urusonin verospiron verospirone xenalon Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, γ-lactone, (7α,17α)- 17α-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7α-mercapto-3-oxo-, γ-lactone, acetate Spiro[17H-cyclopenta[a]phenanthrene-17,2′(5′H)-furan], pregn-4-ene-21-carboxylic acid deriv. SC 9420 3-(3-keto-7α-Acetylthio-17β-hydroxy-4-androsten-17α-yl)propionic acid lactone Aldactone A 17-Hydroxy-7α-mercapto-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone 7-acetate 3-(3-Oxo-7α-acetylthio-17β-hydroxy-4-androsten-17α-yl)propionic acid-γ-lactone Spironolactone A 3′-(3-Oxo-7α-acetylthio-17β-hydroxyandrost-4-en-17α-yl)-propionic acid lactone 7α-Acetylthio-3-oxo-17α-pregn-4-ene-21,17β-carbolactone 7α-(Acetylthio)-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone Spiresis Spirolang Spirone Spirolactone Altex Osyrol Dira Spiro-Tablinen Suracton Spiroctan NSC 150399 Quimolactona Berlactone Novo-Spiroton Spironol MeSH ID: D013148 CaroSpir

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Literature & References

	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
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	5833
Pubchem (sid):	134972759

Publications by PubMed
Serum potassium in stage 5 CKD patients on their first presentation in a dialysis service of a county hospital in western Romania.
Ask the doctor. The June 2013 issue states on page 3 that "it's important to increase potassium intake, particularly if you take a diuretic." But on page 5, it says that if you take spironolactone (which I do), you should avoid high-potassium foods. I'm confused--should I be eating bananas and other potassium-rich foods or not?
Diuretic Exposure in Premature Infants from 1997 to 2011.
A high-throughput chemical screen with FDA approved drugs reveals that the antihypertensive drug Spironolactone impairs cancer cell survival by inhibiting homology directed repair.
Use of different parameters and equations for calculation of IC₅₀ values in efflux assays: potential sources of variability in IC₅₀ determination.
High salt intake does not produce additional impairment in the coronary artery relaxation of spontaneously hypertensive aged rats.
Activation of an apoptotic signal transduction pathway involved in the upregulation of calpain and apoptosis-inducing factor in aldosterone-induced primary cultured cardiomyocytes.
Drug-induced gynecomastia.
Ethics and eplerenone.
11Beta-hydroxylase deficiency and other syndromes of mineralocorticoid excess as a rare cause of endocrine hypertension.
Clinical variability in approaches to polycystic ovary syndrome.
The association between drospirenone and hyperkalemia: a comparative-safety study.
[Pseudoaldosteronism in an elderly man believed to be caused by the health food Shin-Gojoshin].
Eplerenone prevents salt-induced vascular stiffness in Zucker diabetic fatty rats: a preliminary report.
[An elderly man with known heart failure admitted with cardiogenic shock].
Recurrent duodenal ulcer due to nonsteroidal anti-inflammatories following the suspension of antiulcer medication.
Should dermatologists prescribe hormonal contraceptives for acne?
PCOS.
Drug treatments for polycystic ovary syndrome.
Risk of hyperkalemia in women taking ethinylestradiol/drospirenone and other oral contraceptives.
Management strategies for premenstrual syndrome/premenstrual dysphoric disorder.
Influence of spironolactone therapy on thiamine blood levels in patients with heart failure.
Effects of a novel Y5 antagonist in obese mice: combination with food restriction or sibutramine.
Drospirenone/ethinyl estradiol.
Premenstrual syndrome.
Heart failure.
Effects of eplerenone and salt intake on left ventricular remodeling after myocardial infarction in rats.
Reports of hyperkalemia after publication of RALES--a pharmacovigilance study.
Treatment of premenstrual disorders.
Preclinical development of new drugs that enhance thyroid hormone metabolism and clearance: inadequacy of using rats as an animal model for predicting human risks in an IND and NDA.
Agents ameliorating or augmenting the nephrotoxicity of cisplatin and other platinum compounds: a review of some recent research.
Bone loss in rats with aldosteronism.
Diuretics and bone loss in rats with aldosteronism.
Clinical experience with spironolactone in pediatrics.
Eplerenone prevents salt-induced vascular remodeling and cardiac fibrosis in stroke-prone spontaneously hypertensive rats.
New developments in the management of hypertension.
Primary aldosteronism - treatment options.
Selective aldosterone blockade reduces mortality after MI.
Aldosterone receptor antagonists: focus on eplerenone.
Eplerenone.
Eplerenone: a new aldosterone receptor antagonist--are the FDAs restrictions appropriate?
Functional activities of the colon of the desert gerbil (Gerbillus cheesmani).
[Simultaneous analysis of four diuretic drugs by HPLC and its application to health food supplements advertising weight reduction].
Atypical dose-route-dependent food effects of eplerenone in the dog: presence of food effects following intravenous dosing and lack of food effects of following oral dosing.
Cardiac damage prevention by eplerenone: comparison with low sodium diet or potassium loading.
Serum leptin levels in patients with primary hyperaldosteronism before and after treatment: relationships to insulin sensitivity.
Report from the 94th Cardiovascular and Renal Drugs Advisory Committee Meeting, October 11, 2001.
Evaluation of a unique oral contraceptive in the treatment of premenstrual dysphoric disorder.
Reversal of cardiac and renal fibrosis by pirfenidone and spironolactone in streptozotocin-diabetic rats.
Cardiovascular and renal effects of central administration of a mineralocorticoid receptor antagonist in conscious female rats.
Rapid and sensitive reporter gene assays for detection of antiandrogenic and estrogenic effects of environmental chemicals.
Reversal of cardiac fibrosis in deoxycorticosterone acetate-salt hypertensive rats by inhibition of the renin-angiotensin system.
Inhibition of tissue repair by spironolactone: role of mineralocorticoids in fibrous tissue formation.
From GnRH to SSRIs and Beyond: Weighing the Options for Drug Therapy in Premenstrual Syndrome.
Repeated blockade of mineralocorticoid receptors, but not of glucocorticoid receptors impairs food rewarded spatial learning.
Approach to generalized weakness and peripheral neuromuscular disease.
Involvement of type I corticosteroid receptor in the effects of ovariectomy on energy balance.
Treatment of premenstrual syndrome by spironolactone: a double-blind, placebo-controlled study.
Type II corticosteroid receptor stimulation increases NPY gene expression in basomedial hypothalamus of rats.
Electrolyte manipulation in female body-builders.
Steroids and "the pill": early steroid research at Searle.
Dietary restriction sensitizes the rat distal colon to aldosterone.
Effect of chronic treatment with clonidine and spironolactone on cold-induced elevation of blood pressure.
Aldosterone is a physiologically significant kaliuretic hormone.
The metabolism and biopharmaceutics of spironolactone in man.
Influence of food on the bioavailability of spironolactone.
Salt appetite is suppressed by interference with angiotensin II and aldosterone.
Influence of food intake on antihypertensive drugs: spironolactone.
Hormonal and metabolic adaptation to protein-supplemented fasting in obese subjects.
Therapeutic implications of drug interactions with acetaminophen and aspirin.
Metabolic alkalosis in identical twins receiving a low-chloride formula (pseudo-Bartter's syndrome).
[Comparative study of relative biovailability of several spironolactone formulations in a steady-state test (author's transl)].
Influence of food on the bioavailability of drugs.
Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability.
Enhancement by food of canrenone bioavailability from spironolactone.
Spironolactone. III. Canrenone--maximum and minimum steady-state plasma levels.
[Contemporary animal nutrition and its potential hazards to human health (author's transl)].
Salt preference in patients with untreated and treated essential hypertension.
[Sodium balance during fasting and realimentation with special reference to a form of therapy for obesity].
[Instinctive food selection as a disease-regulating factor].

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C07310
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2932.29.5050
MedlinePlusSupp:	View
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: •spironolactone & hydrochlorothiazide: aldactazide (searle). oral: each tablet contains spironolactone 25 mg & hydrochlorothiazide 25 mg. •oral: tablets, film-coated: 25 mg aldactone (with povidone), (pfizer) spironolactone tablets (mutual), spironolactone tablets (mylan), spironolactone tablets (sandoz), spironolactone tablets (udl), spironolactone tablets, (united research); 50 mg aldactone (with povidone; scored), (pfizer), spironolactone tablets (actavis), spironolactone tablets (mutual), spironolactone tablets (mylan), spironolactone tablets (united research); 100 mg aldactone (with povidone; scored), (pfizer), spironolactone tablets (actavis), spironolactone tablets (mutual), spironolactone tablets (mylan), spironolactone tablets (united research). •aldactone •aldactone a •spiresis •spiridon •spirolang •spirone •uractone •verospiron •verospirone

Suppliers

BOC Sciences	Glentham Life Sciences
Penta International	Santa Cruz Biotechnology
Sigma-Aldrich: Sigma	Sinoway Industrial
Penta International Corporation

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	416.58084106445
Vapor Pressure	3.24 mmHg @ 25 °C
Flash Point TCC Value	302.3 °C TCC
logP (o/w)	2.78
Solubility
water, 22 mg/L @ 25 °C (exp)	Yes
water, 28.38 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-human TDLo 5600 mg/kg KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972. oral-man TDLo 5714 ug/kg/4D- 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. oral-man TDLo 7500 ug/kg/3W- BLOOD: AGRANULOCYTOSIS Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000. intraperitoneal-mouse LD50 260 mg/kg Drugs in Japan Vol. 6, Pg. 381, 1982. intravenous-mouse LD50 260 mg/kg Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. oral-mouse LD50 > 1000 mg/kg Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. intraperitoneal-rabbit LD50 866 mg/kg Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. oral-rabbit LD50 > 1000 mg/kg Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. intraperitoneal-rat LD50 277 mg/kg Drugs in Japan Vol. 6, Pg. 381, 1982. oral-rat LD50 > 1000 mg/kg Drugs in Japan Vol. 6, Pg. 381, 1982.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
pharmaceuticals / chemical synthisis
Recommendation for spironolactone usage levels up to:
	not for fragrance use.

Recommendation for spironolactone flavor usage levels up to:
	not for flavor use.

Safety references

EPI System: View

ClinicalTrials.gov:search

Daily Med:search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):52-01-7

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :5833

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

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

Chemidplus:0000052017

RTECS:TU4725000 for cas# 52-01-7