Spironolactone

Identification

Summary

Spironolactone is an aldosterone receptor antagonist used to treat edema, hypertension, heart failure, and aldosteronism.

Brand Names

Aldactazide, Aldactone, Carospir

Generic Name

Spironolactone

DrugBank Accession Number

DB00421

Background

Spironolactone is a potassium-sparing diuretic. It binds to mineralocorticoid receptors and functions as aldosterone antagonists.⁶ It promotes sodium and water excretion and potassium retention.⁷ Spironolactone was originally developed purely for this ability before other pharmacodynamic properties of the drug were discovered.^7,10 It is indicated to treat several conditions, including heart failure, edema, hyperaldosteronism, and hypertension.¹⁴ Off-label uses of spironolactone include hirsutism, female pattern hair loss, and adult acne vulgaris.^4,11

Spironolactone was developed in 1957, marketed in 1959, and approved by the FDA on January 21, 1960.⁹

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 416.573
Monoisotopic: 416.202130202
Chemical Formula: C₂₄H₃₂O₄S

Synonyms

Espironolactona
Spironolactone
Spironolactonum
Spironolattone

External IDs

NSC-150399
SC 9420
SC-9420
SC9420

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Pharmacology

Indication

Spironolactone is indicated for the treatment of the following conditions:

NYHA Class III-IV heart failure and reduced ejection fraction to increase survival, manage edema, and reduce the need for hospitalization for heart failure. Spironolactone is usually administered in conjunction with other heart failure therapies.¹⁴
Hypertension, as add-on therapy, in patients not adequately controlled by other agents.^14,15
Edema associated with hepatic cirrhosis when edema is not responsive to fluid and sodium restriction.^14,15
Edema associated with nephrotic syndrome when treatment of the underlying disease, restriction of fluid and sodium intake, and the use of other diuretics produce an inadequate response.¹⁴
Refractory edema associated with congestive cardiac failure, malignant ascites, hepatic cirrhosis with ascites, and essential hypertension.¹⁵
Short-term preoperative treatment of patients with primary hyperaldosteronism.^14,15
Diagnosis of primary aldosteronism.¹⁵
Long-term maintenance therapy for patients with discrete aldosterone-producing adrenal adenomas who are not candidates for surgery.¹⁴
Long-term maintenance therapy for patients with bilateral micro or macronodular adrenal hyperplasia (idiopathic hyperaldosteronism).¹⁴

As spironolactone has antiandrogenic activity, its off-label uses include the treatment of hirsutism, female pattern hair loss, and adult acne vulgaris.^4,11

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Associated Conditions

Indication Type	Indication	Approval Level	Patient Characteristics	Dose Form
Management of	Edema	••••••••••••
Management of	Edema	••••••••••••
Management of	Hypertension	••••••••••••	••••• •••••••• •••••••••••• ••••••••••
Diagnostic agent	Primary aldosteronism	••••••••••••		••••••••••
Management of	Primary hyperaldosteronism	••••••••••••	••• • ••••••••• ••• •••••••

Associated Therapies

Contraindications & Blackbox Warnings

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Pharmacodynamics

Spironolactone has a potassium-sparing diuretic effect. It promotes sodium and water excretion and potassium retention. It increases renin and aldosterone levels.⁷ Spironolactone is a mineralocorticoid receptor antagonist and has a low affinity for the glucocorticoid receptor.¹³ It also exhibits progestogenic and anti-androgenic actions as it binds to the androgen receptor and, to a lesser extent, estrogen and progesterone receptors.^7,6,11 Spironolactone exhibits anti-inflammatory effects.⁶

Mechanism of action

Aldosterone is a key hormone in the renin-angiotensin-aldosterone system. By binding to the mineralocorticoid receptor at the distal tubules and collecting duct, it causes sodium reabsorption and potassium secretion, increases vascular stiffness and remodelling, and activates pro-inflammatory pathways.^6,11

Spironolactone and its active metabolites are aldosterone antagonists that produce a potassium-sparing diuretic effect. They competitively bind to receptors at the aldosterone-dependent sodium-potassium exchange site in the distal convoluted renal tubule. Spironolactone causes increased amounts of sodium and water to be excreted while potassium is retained. Spironolactone acts both as a diuretic and as an antihypertensive drug by this mechanism. It may be given alone or with other diuretic agents that act more proximally in the renal tubule.^6,14

Target	Actions	Organism
AMineralocorticoid receptor	antagonist	Humans
UGlucocorticoid receptor	antagonist	Humans
UAndrogen receptor	antagonist	Humans
UProgesterone receptor	agonist	Humans
UEstrogen receptor	agonist	Humans
UNuclear receptor subfamily 1 group I member 2	agonist	Humans
UVoltage-dependent L-type calcium channel	inhibitor	Humans

Absorption

The mean time to reach peak plasma concentration of spironolactone and the active metabolite, canrenone, in healthy volunteers is 2.6 and 4.3 hours, respectively. Food increased the bioavailability of spironolactone (as measured by AUC) by approximately 95.4%.¹⁴

Volume of distribution

Not Available

Protein binding

Spironolactone and its metabolites are more than 90% bound to plasma proteins.¹⁴ Spironolactone and canrenone bind to serum albumin and alpha 1-acid glycoprotein.¹

Metabolism

Spironolactone is rapidly and extensively metabolized to form different metabolites. A group of metabolites are formed when sulfur of spironolactone is removed, such as canrenone. Sulfur is retained in another group of metabolites, including 7-alpha (α)-thiomethylspironolactone (TMS) and 6-beta (ß)-hydroxy-7-alpha (α)-thiomethylspirolactone (HTMS).¹⁴

Spironolactone is firstly deacetylated to 7-α-thiospironolactone.^2,3,5 7-α-thiospironolactone is S-methylated to TMS, which is the primary metabolite,^7,8,12 or dethioacetylated to canrenone.^2,3,12 TMS and HTMS can be further metabolized.^2,3,12

In humans, the potencies of TMS and 7-α-thiospirolactone in reversing the effects of the synthetic mineralocorticoid, fludrocortisone, on urinary electrolyte composition were approximately a third relative to spironolactone. However, since the serum concentrations of these steroids were not determined, their incomplete absorption and/or first-pass metabolism could not be ruled out as a reason for their reduced in vivo activities.¹⁴

Hover over products below to view reaction partners

Spironolactone
- 7-alpha-thiospironolactone
  - 7-alpha-thiomethylspironolactone
  - Canrenone

Route of elimination

The metabolites are excreted primarily in the urine and secondarily in bile.¹⁴ Metabolites of spironolactone are excreted in urine (42-56%) and in the feces (14.2-14.6%). No unmetabolized spironolactone is present in the urine.⁵

Half-life

The mean half-life of spironolactone is 1.4 hours. The mean half-life values of its metabolites, including canrenone, TMS, and HTMS are 16.5, 13.8, and 15 hours, respectively.¹⁴

Clearance

Not Available

Adverse Effects

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Toxicity

The oral LD₅₀ of spironolactone is greater than 1000 mg/kg in mice, rats, and rabbits.¹⁴

Acute overdosage of ALDACTONE may be manifested by drowsiness, mental confusion, maculopapular or erythematous rash, nausea, vomiting, dizziness, or diarrhea. Rarely, instances of hyponatremia, hyperkalemia,or hepatic coma may occur in patients with severe liver disease, but these are unlikely due to acute overdosage. Hyperkalemia may occur, especially in patients with impaired renal function. In case of an overdose, vomiting may be induced and gastric lavage may be instituted. As there is no specific antidote, treatment is supportive to maintain hydration, electrolyte balance, and vital functions. Patients who have renal impairment may develop hyperkalemia. In such cases, discontinue spironolactone.¹⁴

Pathways

Pathway	Category
Spironolactone Action Pathway	Drug action

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Spironolactone may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
Abaloparatide	The risk or severity of adverse effects can be increased when Spironolactone is combined with Abaloparatide.
Abiraterone	The therapeutic efficacy of Abiraterone can be decreased when used in combination with Spironolactone.
Acebutolol	The risk or severity of hyperkalemia can be increased when Acebutolol is combined with Spironolactone.
Aceclofenac	The risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Spironolactone.

Food Interactions

Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
Take with or without food. Food increases the bioavailability of spironolactone by approximately 95.4%. It should be taken at a consistent time in regards to food.

Products

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Product Images

International/Other Brands

Osyrol / Spiresis / Spiretic / Spiroctan / Uractone / Verospiron / Xenalon

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Aldactone	Tablet, film coated	25 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1960-01-21	Not applicable
Aldactone	Tablet, film coated	100 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1960-01-21	Not applicable
Aldactone	Tablet, film coated	50 mg/1	Oral	Physicians Total Care, Inc.	1995-04-24	2011-06-30
Aldactone	Tablet, film coated	25 mg/1	Oral	REMEDYREPACK INC.	2018-08-31	2020-05-20
Aldactone	Tablet, film coated	50 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1960-01-21	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Jamp Spironolactone	Tablet	100 mg	Oral	Jamp Pharma Corporation	2022-07-14	Not applicable
Jamp Spironolactone	Tablet	25 mg	Oral	Jamp Pharma Corporation	2022-07-14	Not applicable
Mint-spironolactone	Tablet	25 mg	Oral	Mint Pharmaceuticals Inc	2020-02-06	Not applicable
Mint-spironolactone	Tablet	100 mg	Oral	Mint Pharmaceuticals Inc	2020-02-06	Not applicable
Ntp-spironolactone	Tablet	100 mg	Oral	Nt Pharma Canada Ltd	Not applicable	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
AKTAZİD 25 MG/25 MG FİLM KAPLI TABLET, 100 ADET	Spironolactone (25 mg) + Hydrochlorothiazide (25 mg)	Tablet, film coated	Oral	World Medicine Ilac San. Ve Tic. a.s.	2020-08-14	Not applicable
AKTAZİD 25 MG/25 MG FİLM KAPLI TABLET, 20 ADET	Spironolactone (25 mg) + Hydrochlorothiazide (25 mg)	Tablet, film coated	Oral	World Medicine Ilac San. Ve Tic. a.s.	2020-08-14	Not applicable
AKTAZİD 25 MG/25 MG FİLM KAPLI TABLET, 30 ADET	Spironolactone (25 mg) + Hydrochlorothiazide (25 mg)	Tablet, film coated	Oral	World Medicine Ilac San. Ve Tic. a.s.	2017-11-02	Not applicable
AKTAZİD 25 MG/25 MG FİLM KAPLI TABLET, 50 ADET	Spironolactone (25 mg) + Hydrochlorothiazide (25 mg)	Tablet, film coated	Oral	World Medicine Ilac San. Ve Tic. a.s.	2020-08-14	Not applicable
AKTAZİD 50 MG/50 MG FİLM KAPLI TABLET, 100 ADET	Spironolactone (50 mg) + Hydrochlorothiazide (50 mg)	Tablet, film coated	Oral	World Medicine Ilac San. Ve Tic. a.s.	2020-08-14	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
011054 Niacinamide 4% / Spironolactone 5%	Spironolactone (5 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2020-07-02	Not applicable
011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025%	Spironolactone (5 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.025 g/100g)	Gel	Topical	Sincerus Florida, LLC	2020-07-02	Not applicable
011220 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05%	Spironolactone (5 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.05 g/100g)	Gel	Topical	Sincerus Florida, LLC	2020-07-02	Not applicable
011503 Dapsone 6% / Niacinamide 2% / Spironolactone 5%	Spironolactone (5 g/100g) + Dapsone (6 g/100g) + Nicotinamide (2 g/100g)	Gel	Topical	Sincerus Florida, LLC	2020-07-02	Not applicable
Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2%	Spironolactone (2 g/100g) + Benzoyl peroxide (5 g/100g) + Clindamycin phosphate (1 g/100g) + Nicotinamide (2 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-11	Not applicable

Chemical Identifiers

UNII: 27O7W4T232
CAS number: 52-01-7
InChI Key: LXMSZDCAJNLERA-ZHYRCANASA-N
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
IUPAC Name: (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
SMILES: [H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@]([H])(CC2=CC(=O)CC[C@]12C)SC(C)=O

References

Synthesis Reference

Giuseppe Bernini, "Process for preparing micronized spironolactone." U.S. Patent US4332721, issued July, 1975.

US4332721

General References

Takamura N, Maruyama T, Ahmed S, Suenaga A, Otagiri M: Interactions of aldosterone antagonist diuretics with human serum proteins. Pharm Res. 1997 Apr;14(4):522-6. [Article]
LaCagnin LB, Lutsie P, Colby HD: Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes. Biochem Pharmacol. 1987 Oct 15;36(20):3439-44. [Article]
Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD: Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites. Drug Metab Dispos. 1994 Nov-Dec;22(6):903-8. [Article]
Kim GK, Del Rosso JQ: Oral Spironolactone in Post-teenage Female Patients with Acne Vulgaris: Practical Considerations for the Clinician Based on Current Data and Clinical Experience. J Clin Aesthet Dermatol. 2012 Mar;5(3):37-50. [Article]
Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. [Article]
Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. [Article]
Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. [Article]
Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, Stubbs K, Smith M, Karim A: Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites. J Clin Pharmacol. 1989 Apr;29(4):342-7. [Article]
Menard J: The 45-year story of the development of an anti-aldosterone more specific than spironolactone. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):45-52. doi: 10.1016/j.mce.2003.10.008. [Article]
BOLTE E, VERDY M, MARC-AURELE J, BROUILLET J, BEAUREGARD P, GENEST J: Studies on new diuretic compounds: spirolactone and chlorothiazide. Can Med Assoc J. 1958 Dec 1;79(11):881-8. [Article]
Patibandla S, Heaton J, Kyaw H: Spironolactone. . [Article]
Overdiek HW, Merkus FW: The metabolism and biopharmaceutics of spironolactone in man. Rev Drug Metab Drug Interact. 1987;5(4):273-302. doi: 10.1515/dmdi.1987.5.4.273. [Article]
Rogerson FM, Yao YZ, Smith BJ, Dimopoulos N, Fuller PJ: Determinants of spironolactone binding specificity in the mineralocorticoid receptor. J Mol Endocrinol. 2003 Dec;31(3):573-82. [Article]
FDA Approved Drug Products: ALDACTONE (spironolactone) tablets, for oral use (December 2022) [Link]
EMA Approved Drug Products: QAIALDO (spironolactone) Oral Suspension [Link]

External Links

Human Metabolome Database: HMDB0014565
KEGG Drug: D00443
KEGG Compound: C07310
PubChem Compound: 5833
PubChem Substance: 46508525
ChemSpider: 5628
BindingDB: 50228080
RxNav: 9997
ChEBI: 9241
ChEMBL: CHEMBL1393
ZINC: ZINC000003861599
Therapeutic Targets Database: DAP000297
PharmGKB: PA451483
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: SNL
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Spironolactone

PDB Entries

2ab2 / 2oax / 3vhu

FDA label

Download (204 KB)

MSDS

Download (72.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Basic Science	Healthy Subjects (HS) / Hypoglycemia	1
4	Completed	Diagnostic	Heart Failure	1
4	Completed	Diagnostic	Heart Failure / Nonischemic Dilated Cardiomyopathy	1
4	Completed	Prevention	Anthracycline Induced Cardiotoxicity	1
4	Completed	Prevention	Cirrhosis of the Liver / Portal Hypertension	1

Pharmacoeconomics

Manufacturers

Gd searle llc
Actavis elizabeth llc
Amneal pharmaceuticals
Ascot hosp pharmaceuticals inc div travenol laboratories inc
Ivax pharmaceuticals inc
Lederle laboratories div american cyanamid co
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Purepac pharmaceutical co
Sandoz inc
Superpharm corp
Upsher smith laboratories inc
Vangard laboratories inc div midway medical co
Vintage pharmaceuticals llc
Warner chilcott div warner lambert co
Watson laboratories inc

Packagers

Actavis Group
Advanced Pharmaceutical Services Inc.
Amerisource Health Services Corp.
A-S Medication Solutions LLC
Cardinal Health
Caremark LLC
Comprehensive Consultant Services Inc.
Dept Health Central Pharmacy
DHHS Program Support Center Supply Service Center
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
GD Searle LLC
Greenstone LLC
Guna Inc.
H and H Laboratories
Heartland Repack Services LLC
Innoviant Pharmacy Inc.
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Major Pharmaceuticals
Mckesson Corp.
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mutual Pharmaceutical Co.
Mylan
Neighborcare Repackaging Inc.
Neuman Distributors Inc.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
PD-Rx Pharmaceuticals Inc.
Pfizer Inc.
Pharmaceutical Utilization Management Program VA Inc.
Pharmacia Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Professional Co.
Qualitest
Rebel Distributors Corp.
Remedy Repack
Resource Optimization and Innovation LLC
Richmond Pharmacy
Sandhills Packaging Inc.
Sandoz
Southwood Pharmaceuticals
UDL Laboratories
Vangard Labs Inc.
Vintage Pharmaceuticals Inc.

Dosage Forms

Form	Route	Strength
Capsule	Oral	25 MG
Pill		100 MG
Tablet, coated	Oral	100 MG
Capsule	Oral	100 mg
Tablet, coated	Oral	50 mg
Tablet	Oral	25.000 mg
Tablet	Oral	100. mg
Tablet	Oral	2500000 mg
Suspension	Oral	25 mg/5mL
Tablet, film coated	Oral
Tablet	Oral	10000000 mg
Capsule, coated	Oral
Capsule	Oral
Gel	Topical
Capsule	Oral
Suspension	Oral	10 mg/ml
Tablet	Oral
Capsule	Oral	50 MG
Tablet, film coated	Oral	100 mg
Tablet, coated	Oral	25 mg
Tablet, delayed release	Oral	100 mg
Tablet	Oral	50 MG
Tablet, film coated	Oral	50 MG
Tablet	Oral	100 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	50 mg/1
Tablet, coated	Oral	100 mg/1
Tablet, coated	Oral	25 mg/1
Tablet, coated	Oral	50 mg/1
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	25 mg/1
Tablet, film coated	Oral	50 mg/1
Tablet	Oral
Tablet, film coated	Oral
Tablet	Oral	100 mg
Tablet	Oral	25 mg
Tablet, film coated	Oral	25 mg

Prices

Unit description	Cost	Unit
Spironolactone powder	12.56USD	g
Aldactone 100 mg tablet	2.14USD	tablet
Aldactazide 50-50 mg tablet	2.02USD	tablet
Aldactazide 50-50 tablet	1.92USD	tablet
Aldactone 50 mg tablet	1.84USD	tablet
Spironolactone 100 mg tablet	1.45USD	tablet
Aldactazide 25-25 mg tablet	1.26USD	tablet
Aldactazide 25-25 tablet	1.04USD	tablet
Spironolactone 50 mg tablet	0.83USD	tablet
Aldactone 25 mg tablet	0.8USD	tablet
Spironolactone-HCTZ 25-25 mg tablet	0.57USD	tablet
Spironolactone 25 mg tablet	0.5USD	tablet
Novo-Spiroton 100 mg Tablet	0.25USD	tablet
Novo-Spiroton 25 mg Tablet	0.11USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US9757394	No	2017-09-12	2036-10-28
US10493083	No	2019-12-03	2036-10-28
US10624906	No	2020-04-21	2036-10-28
US10660907	No	2020-05-26	2036-10-28
US10888570	No	2021-01-12	2036-10-28
US11395828	No	2016-10-28	2036-10-28
US11389461	No	2016-10-28	2036-10-28
US11491166	No	2016-10-28	2036-10-28

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	198-207	https://www.fishersci.com/store/msds?partNumber=AC207460050&productDescription=SPIRONOLACTONE+SPIRONOLACT&vendorId=VN00032119&countryCode=US&language=en
logP	2.78	https://www.ncbi.nlm.nih.gov/pubmed/26642673

Predicted Properties

Property	Value	Source
Water Solubility	0.00198 mg/mL	ALOGPS
logP	3.1	ALOGPS
logP	3.64	Chemaxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	17.89	Chemaxon
pKa (Strongest Basic)	-4.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	60.44 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	113.5 m³·mol^-1	Chemaxon
Polarizability	46.03 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9912
Blood Brain Barrier	+	0.932
Caco-2 permeable	+	0.5432
P-glycoprotein substrate	Substrate	0.5691
P-glycoprotein inhibitor I	Inhibitor	0.6807
P-glycoprotein inhibitor II	Inhibitor	0.8388
Renal organic cation transporter	Non-inhibitor	0.727
CYP450 2C9 substrate	Non-substrate	0.7897
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.6638
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9276
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8681
Ames test	Non AMES toxic	0.9158
Carcinogenicity	Non-carcinogens	0.9288
Biodegradation	Not ready biodegradable	0.9696
Rat acute toxicity	2.0150 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9427
hERG inhibition (predictor II)	Non-inhibitor	0.7002

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0h2u-0109000000-b5dcae38bb499eaabba7
Mass Spectrum (Electron Ionization)	MS	splash10-0006-9836000000-9f600bd39c3b914c0b17
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0000900000-5e2e1944e45fcef225d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0000900000-406c100eed5b6cdc3286
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0005900000-2281d6a738d3d492b753
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05nf-1229200000-e2d9fa89e5e355517b03
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00xr-2009500000-f64e1194391e1d221187
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-2009300000-5011d7fba923ed4d4aa1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-06r6-8829100000-6ea2d70d5cb38139b402
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-9007200000-208992f59d97f539818a
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	213.835082	predicted	DarkChem Lite v0.1.0
[M-H]-	212.582282	predicted	DarkChem Lite v0.1.0
[M-H]-	215.036482	predicted	DarkChem Lite v0.1.0
[M-H]-	209.46205	predicted	DeepCCS 1.0 (2019)
[M+H]+	214.999482	predicted	DarkChem Lite v0.1.0
[M+H]+	213.098082	predicted	DarkChem Lite v0.1.0
[M+H]+	215.847282	predicted	DarkChem Lite v0.1.0
[M+H]+	211.28694	predicted	DeepCCS 1.0 (2019)
[M+Na]+	214.538282	predicted	DarkChem Lite v0.1.0
[M+Na]+	212.488382	predicted	DarkChem Lite v0.1.0
[M+Na]+	215.573082	predicted	DarkChem Lite v0.1.0
[M+Na]+	217.39592	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1.6	N/A	N/A	A28052
IC 50 (nM)	13	N/A	N/A	A28202
IC 50 (nM)	60	N/A	N/A	A28203
IC 50 (nM)	49	N/A	N/A	A28203
Ki (nM)	2.323	N/A	N/A	A28201

Details1. Mineralocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Zinc ion binding
Specific Function: Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name: NR3C2
Uniprot ID: P08235
Uniprot Name: Mineralocorticoid receptor
Molecular Weight: 107066.575 Da

References

Sitruk-Ware R: Progestogens in hormonal replacement therapy: new molecules, risks, and benefits. Menopause. 2002 Jan-Feb;9(1):6-15. [Article]
Rogerson FM, Yao YZ, Smith BJ, Dimopoulos N, Fuller PJ: Determinants of spironolactone binding specificity in the mineralocorticoid receptor. J Mol Endocrinol. 2003 Dec;31(3):573-82. [Article]
Gertner RA, Klein JD, Bailey JL, Kim DU, Luo XH, Bagnasco SM, Sands JM: Aldosterone decreases UT-A1 urea transporter expression via the mineralocorticoid receptor. J Am Soc Nephrol. 2004 Mar;15(3):558-65. [Article]
Frishman WH, Stier CT Jr: Aldosterone and aldosterone antagonism in systemic hypertension. Curr Hypertens Rep. 2004 Jun;6(3):195-200. [Article]
Rogerson FM, Yao Y, Smith BJ, Fuller PJ: Differences in the determinants of eplerenone, spironolactone and aldosterone binding to the mineralocorticoid receptor. Clin Exp Pharmacol Physiol. 2004 Oct;31(10):704-9. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. [Article]
Rossi G, Boscaro M, Ronconi V, Funder JW: Aldosterone as a cardiovascular risk factor. Trends Endocrinol Metab. 2005 Apr;16(3):104-7. [Article]
FDA Approved Drug Products: ALDACTONE (spironolactone) tablets, for oral use (December 2022) [Link]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	6920	N/A	N/A	A28202
IC 50 (nM)	1400	N/A	N/A	A28203
Ki (nM)	32.6	N/A	N/A	A28201

Details2. Glucocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Zinc ion binding
Specific Function: Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name: NR3C1
Uniprot ID: P04150
Uniprot Name: Glucocorticoid receptor
Molecular Weight: 85658.57 Da

References

Fagart J, Hillisch A, Huyet J, Barfacker L, Fay M, Pleiss U, Pook E, Schafer S, Rafestin-Oblin ME, Kolkhof P: A new mode of mineralocorticoid receptor antagonism by a potent and selective nonsteroidal molecule. J Biol Chem. 2010 Sep 24;285(39):29932-40. doi: 10.1074/jbc.M110.131342. Epub 2010 Jul 22. [Article]
Rogerson FM, Yao YZ, Smith BJ, Dimopoulos N, Fuller PJ: Determinants of spironolactone binding specificity in the mineralocorticoid receptor. J Mol Endocrinol. 2003 Dec;31(3):573-82. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	523	N/A	N/A	A28202
IC 50 (nM)	120	N/A	N/A	A28203
Ki (nM)	39.4	N/A	N/A	A28201

Details3. Androgen receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist
Curator comments: A11837, A178192, A261025

General Function: Zinc ion binding
Specific Function: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name: AR
Uniprot ID: P10275
Uniprot Name: Androgen receptor
Molecular Weight: 98987.9 Da

References

Ye P, Yamashita T, Pollock DM, Sasano H, Rainey WE: Contrasting effects of eplerenone and spironolactone on adrenal cell steroidogenesis. Horm Metab Res. 2009 Jan;41(1):35-9. doi: 10.1055/s-0028-1087188. Epub 2008 Sep 25. [Article]
Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. [Article]
Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. [Article]
Patibandla S, Heaton J, Kyaw H: Spironolactone. . [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>10000	N/A	N/A	A28202
IC 50 (nM)	650	N/A	N/A	A28203
Ki (nM)	399.7	N/A	N/A	A28201

Details4. Progesterone receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Zinc ion binding
Specific Function: The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name: PGR
Uniprot ID: P06401
Uniprot Name: Progesterone receptor
Molecular Weight: 98979.96 Da

References

Fagart J, Hillisch A, Huyet J, Barfacker L, Fay M, Pleiss U, Pook E, Schafer S, Rafestin-Oblin ME, Kolkhof P: A new mode of mineralocorticoid receptor antagonism by a potent and selective nonsteroidal molecule. J Biol Chem. 2010 Sep 24;285(39):29932-40. doi: 10.1074/jbc.M110.131342. Epub 2010 Jul 22. [Article]
Fernandez MD, Carter GD, Palmer TN: The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol. Br J Clin Pharmacol. 1983 Jan;15(1):95-101. doi: 10.1111/j.1365-2125.1983.tb01470.x. [Article]

Details5. Estrogen receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Zinc ion binding
Specific Function: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...

Components:

Name	UniProt ID
Estrogen receptor	P03372
Estrogen receptor beta	Q92731

References

Fernandez MD, Carter GD, Palmer TN: The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol. Br J Clin Pharmacol. 1983 Jan;15(1):95-101. doi: 10.1111/j.1365-2125.1983.tb01470.x. [Article]
Levy J, Burshell A, Marbach M, Afllalo L, Glick SM: Interaction of spironolactone with oestradiol receptors in cytosol. J Endocrinol. 1980 Mar;84(3):371-9. doi: 10.1677/joe.0.0840371. [Article]

Details6. Nuclear receptor subfamily 1 group I member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Zinc ion binding
Specific Function: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name: NR1I2
Uniprot ID: O75469
Uniprot Name: Nuclear receptor subfamily 1 group I member 2
Molecular Weight: 49761.245 Da

References

Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]

Details7. Voltage-dependent L-type calcium channel (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Voltage-gated calcium channel activity
Specific Function: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:

Name	UniProt ID
Voltage-dependent L-type calcium channel subunit alpha-1C	Q13936
Voltage-dependent L-type calcium channel subunit alpha-1D	Q01668
Voltage-dependent L-type calcium channel subunit alpha-1F	O60840
Voltage-dependent L-type calcium channel subunit alpha-1S	Q13698
Voltage-dependent L-type calcium channel subunit beta-1	Q02641
Voltage-dependent L-type calcium channel subunit beta-2	Q08289
Voltage-dependent L-type calcium channel subunit beta-3	P54284
Voltage-dependent L-type calcium channel subunit beta-4	O00305
Voltage-dependent P/Q-type calcium channel subunit alpha-1A	O00555

References

Sorrentino R, Autore G, Cirino G, d'Emmanuele de Villa Bianca R, Calignano A, Vanasia M, Alfieri C, Sorrentino L, Pinto A: Effect of spironolactone and its metabolites on contractile property of isolated rat aorta rings. J Cardiovasc Pharmacol. 2000 Aug;36(2):230-5. [Article]
Dacquet C, Loirand G, Mironneau C, Mironneau J, Pacaud P: Spironolactone inhibition of contraction and calcium channels in rat portal vein. Br J Pharmacol. 1987 Nov;92(3):535-44. doi: 10.1111/j.1476-5381.1987.tb11354.x. [Article]
Mironneau J: Calcium channel antagonist effects of spironolactone, an aldosterone antagonist. Am J Cardiol. 1990 Jun 19;65(23):7K-8K; discussion 3K. doi: 10.1016/0002-9149(90)91267-a. [Article]

Enzymes

Details1. Cytochrome P450 11B1, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Steroid 11-beta-monooxygenase activity
Specific Function: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name: CYP11B1
Uniprot ID: P15538
Uniprot Name: Cytochrome P450 11B1, mitochondrial
Molecular Weight: 57572.44 Da

References

Cheng SC, Suzuki K, Sadee W, Harding BW: Effects of spironolactone, canrenone and canrenoate-K on cytochrome P450, and 11beta- and 18-hydroxylation in bovine and human adrenal cortical mitochondria. Endocrinology. 1976 Oct;99(4):1097-106. [Article]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Details2. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]

Details3. Cytochrome P450 11B2, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid 11-beta-monooxygenase activity
Specific Function: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name: CYP11B2
Uniprot ID: P19099
Uniprot Name: Cytochrome P450 11B2, mitochondrial
Molecular Weight: 57559.62 Da

References

Cheng SC, Suzuki K, Sadee W, Harding BW: Effects of spironolactone, canrenone and canrenoate-K on cytochrome P450, and 11beta- and 18-hydroxylation in bovine and human adrenal cortical mitochondria. Endocrinology. 1976 Oct;99(4):1097-106. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Takamura N, Maruyama T, Ahmed S, Suenaga A, Otagiri M: Interactions of aldosterone antagonist diuretics with human serum proteins. Pharm Res. 1997 Apr;14(4):522-6. [Article]

Details2. alpha1-acid glycoprotein (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:

Name	UniProt ID
Alpha-1-acid glycoprotein 1	P02763
Alpha-1-acid glycoprotein 2	P19652

References

Takamura N, Maruyama T, Ahmed S, Suenaga A, Otagiri M: Interactions of aldosterone antagonist diuretics with human serum proteins. Pharm Res. 1997 Apr;14(4):522-6. [Article]

Transporters

Details1. Canalicular multispecific organic anion transporter 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Organic anion transmembrane transporter activity
Specific Function: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name: ABCC2
Uniprot ID: Q92887
Uniprot Name: Canalicular multispecific organic anion transporter 1
Molecular Weight: 174205.64 Da

References

Johnson DR, Klaassen CD: Regulation of rat multidrug resistance protein 2 by classes of prototypical microsomal enzyme inducers that activate distinct transcription pathways. Toxicol Sci. 2002 Jun;67(2):182-9. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	23600	N/A	N/A	A15871

Details2. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Rigalli JP, Ruiz ML, Perdomo VG, Villanueva SS, Mottino AD, Catania VA: Pregnane X receptor mediates the induction of P-glycoprotein by spironolactone in HepG2 cells. Toxicology. 2011 Jul 11;285(1-2):18-24. doi: 10.1016/j.tox.2011.03.015. Epub 2011 Apr 1. [Article]

Details3. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name: SLCO1A2
Uniprot ID: P46721
Uniprot Name: Solute carrier organic anion transporter family member 1A2
Molecular Weight: 74144.105 Da

References

Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. [Article]

Details4. Bile salt export pump

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Transporter activity
Specific Function: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name: ABCB11
Uniprot ID: O95342
Uniprot Name: Bile salt export pump
Molecular Weight: 146405.83 Da

References

Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Spironolactone

Identification

Structure for Spironolactone (DB00421)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

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Components:

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Components:

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Enzymes

References

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Carriers

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Components:

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Transporters

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