Identification

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Name
Spironolactone
Accession Number
DB00421  (APRD01234)
Type
Small Molecule
Groups
Approved
Description

Spironolactone is a potassium sparing diuretic like eplerenone that competitively inhibits mineralocorticoid receptors in the distal convoluted tubule to promote sodium and water excretion and potassium retention.8. Spironolactone was originally developed purely for this ability before other pharmacodynamic properties of the drug were discovered.8,11 It is indicated to treat a number of conditions including heart failure, deem, hyperaldosteronism, adrenal hyperplasia, hypertension, and nephrotic syndrome.Label Off label uses of spironolactone involving its antiandrogenic activity include hirsutism, female pattern hair loss, and adult acne vulgaris.4 Spironolactone is also frequently used in medical gender transition.5

Spironolactone was developed in 1957, marketed in 1959, and approved by the FDA on January 21, 1960.10,12

Structure
Thumb
Synonyms
  • Espironolactona
  • Spironolactone
  • Spironolactonum
  • Spironolattone
External IDs
NSC-150399 / SC-9420
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AldactoneTablet, film coated50 mg/1OralPhysicians Total Care, Inc.1995-04-242011-06-30Us
AldactoneTablet, film coated25 mg/1OralREMEDYREPACK INC.2018-08-31Not applicableUs
AldactoneTablet, film coated100 mg/1OralG.D. Searle LLC Division of Pfizer Inc1960-01-21Not applicableUs
AldactoneTablet, film coated50 mg/1OralG.D. Searle LLC Division of Pfizer Inc1960-01-21Not applicableUs
AldactoneTablet, film coated25 mg/1OralG.D. Searle LLC Division of Pfizer Inc1960-01-21Not applicableUs
Aldactone 100 mgTabletOralPfizer Canada Ulc1975-12-31Not applicableCanada
Aldactone 25 mgTabletOralPfizer Canada Ulc1959-12-31Not applicableCanada
CaroSpirSuspension25 mg/5mLOralAtlantic Biologicals Corp.2018-08-22Not applicableUs
CaroSpirSuspension25 mg/5mLOralCmp Pharma, Inc.2017-08-04Not applicableUs
SpironolactoneTablet, film coated50 mg/1OralVintage Pharmaceuticals, LLC2006-10-312006-10-31Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mint-spironolactoneTabletOralMint Pharmaceuticals IncNot applicableNot applicableCanada
Mint-spironolactoneTabletOralMint Pharmaceuticals IncNot applicableNot applicableCanada
Ntp-spironolactoneTabletOralNt Pharma Canada LtdNot applicableNot applicableCanada
Ntp-spironolactoneTabletOralNt Pharma Canada LtdNot applicableNot applicableCanada
SpironolactoneTablet25 mg/1OralREMEDYREPACK INC.2017-04-24Not applicableUs
SpironolactoneTablet50 mg/1OralAmerican Health Packaging2019-06-01Not applicableUs
SpironolactoneTablet, film coated50 mg/1OralProficient Rx LP2017-06-02Not applicableUs
SpironolactoneTablet, film coated25 mg/1OralSt. Mary's Medical Park Pharmacy2018-09-27Not applicableUs
SpironolactoneTablet, film coated25 mg/1Oralbryant ranch prepack2017-06-02Not applicableUs
SpironolactoneTablet, film coated50 mg/1OralA-S Medication Solutions2013-02-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AldactazideSpironolactone (50 mg/1) + Hydrochlorothiazide (50 mg/1)Tablet, film coatedOralG.D. Searle LLC Division of Pfizer Inc1978-01-01Not applicableUs00025 1021 31 nlmimage10 b146d8b6
AldactazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralG.D. Searle LLC Division of Pfizer Inc1978-01-01Not applicableUs
Aldactazide 25Spironolactone (25 mg) + Hydrochlorothiazide (25 mg)TabletOralPfizer Canada Ulc1960-12-31Not applicableCanada
Aldactazide 50Spironolactone (50 mg) + Hydrochlorothiazide (50 mg)TabletOralPfizer Canada Ulc1983-12-31Not applicableCanada
Apo-spirozide TabSpironolactone (25 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation1991-12-312011-08-05Canada
Spironolactone and HydrochlorothiazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralPhysicians Total Care, Inc.1993-05-26Not applicableUs54868 069920180907 15195 16vhh6y
Spironolactone and HydrochlorothiazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralGreenstone LLC1978-01-01Not applicableUs
Spironolactone and HydrochlorothiazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralAmerincan Health Packaging2015-03-312018-02-28Us53489 0144 01 nlmimage10 4f0ea785
Spironolactone and HydrochlorothiazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralSun Pharmaceutical Industries, Inc.1987-07-02Not applicableUs
Spironolactone and HydrochlorothiazideSpironolactone (25 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMylan Institutional1994-04-112018-11-30Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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)GelTopicalSincerus Florida, LLC2019-05-11Not applicableUs
Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.025%Spironolactone (2 g/100g) + Benzoyl peroxide (5 g/100g) + Clindamycin phosphate (1 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.025 g/100g)GelTopicalSincerus Florida, LLC2019-05-04Not applicableUs
Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.05%Spironolactone (2 g/100g) + Benzoyl peroxide (5 g/100g) + Clindamycin phosphate (1 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.05 g/100g)GelTopicalSincerus Florida LLC2019-05-03Not applicableUs
Clindamycin 1% / Niacinamide 4% / Spironolactone 2% / Tretinoin 0.025%Spironolactone (2 g/100g) + Clindamycin phosphate (1 g/100g) + Nicotinamide (4 g/100g) + Tretinoin (0.025 g/100g)GelTopicalSincerus Florida, LLC2019-05-04Not applicableUs
Dapsone 6% / Niacinamide 2% / Spironolactone 5%Spironolactone (5 g/100g) + Dapsone (6 g/100g) + Nicotinamide (2 g/100g)GelTopicalSincerus Florida, LLC2019-05-11Not applicableUs
Dapsone 8.5% / Niacinamide 2% / Spironolactone 5%Spironolactone (5 g/100g) + Dapsone (8.5 g/100g) + Nicotinamide (2 g/100g)GelTopicalSincerus Florida, LLC2019-05-10Not applicableUs
Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025%Spironolactone (5 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.025 g/100g)GelTopicalSincerus Florida, LLC2019-05-04Not applicableUs
Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05%Spironolactone (5 g/100g) + Nicotinamide (2 g/100g) + Tretinoin (0.05 g/100g)GelTopicalSincerus Florida LLC2019-05-03Not applicableUs
Niacinamide 4% / Spironolactone 5%Spironolactone (5 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2019-05-10Not applicableUs
International/Other Brands
Osyrol / Spiresis / Spiretic / Spiroctan / Uractone / Verospiron / Xenalon
Categories
UNII
27O7W4T232
CAS number
52-01-7
Weight
Average: 416.573
Monoisotopic: 416.202130202
Chemical Formula
C24H32O4S
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
(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
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

Pharmacology

Indication

Spironolactone is indicated for the treatment of New York Heart Association Class III-IV heart failure, management of edema in cirrhotic adults not responsive to fluid and sodium restrictions, primary hyperaldosteronism short-term preoperatively, primary hyperaldosteronism long-term in patients with aldosterone producing adrenal adenomas that are not candidates for surgery or patients with bilarteral micro/macronodular adrenal hyperplasia, as an add-on therapy in hypertension, and in nephrotic syndrome when treatment of the disease as well as fluid and sodium restriction with other diuretics is inadequate.Label

Spironolactone has antiandrogenic activity which leads to many of its off label uses. Spironolactone is used off label in the treatment of hirsutism, female pattern hair loss, and adult acne vulgaris.4

Spironolactone is also frequently used for its antiandrogenic effects in transgender female patients due to its low cost and reducing male-pattern hair growth.5

Associated Conditions
Pharmacodynamics

Originally spironolactone was only studied for its potassium sparing diuretic effect.8 Spironolactone competitively inhibits mineralocorticoid receptors in the distal convoluted tubule to promote sodium and water excretion and potassium retention.8. Inhibition of this receptor leads to increased renin and aldosterone levels.8

Spironolactone is structurally similar to progesterone and as a result is associated with progestogenic and antiandrogenic effects.8

Mechanism of action

Spironolactone competitively inhibits aldosterone dependant sodium potassium exchange channels in the distal convoluted tubule.Label This action leads to increased sodium and water excretion, but more potassium retention.Label The increased excretion of water leads to diuretic and also antihypertensive effects.Label

TargetActionsOrganism
AMineralocorticoid receptor
antagonist
Humans
UAndrogen receptor
antagonist
Humans
UProgesterone receptor
agonist
Humans
UGlucocorticoid receptor
antagonist
Humans
UCytochrome P450 11B2, mitochondrial
antagonist
Humans
USteroid 17-alpha-hydroxylase/17,20 lyase
antagonist
Humans
U3-oxo-5-alpha-steroid 4-dehydrogenase
antagonist
Humans
USex hormone-binding globulin
binder
Humans
UVoltage-dependent calcium channel
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
Additional Data Available
Adverse Effects

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Contraindications

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Absorption

Spironolactone reaches a maximum concentration in 2.6 hours and an active metabolite (canrenone) reaches a maximum concentration in 4.3 hours.Label When taken with food, the bioavailability of spironolactone increases to 95.4%.Label

Giving spironolactone with food increases the maximum concentration from 209ng/mL to 301ng/mL.6 The time to maximum concentration also increases from 2.28 hours to 3.05 hours.6 The area under the curve varies from 2103ng/mL*hr to 4544ng/mL*hr.6

Volume of distribution

Volume of distribution data is not readily available.Label,7

Protein binding

>90%.Label Canrenone is as much as 98% protein bound.6

Metabolism

Spironolactone is deacetylated to 7α-thiospironolactone.2,3 7α-thiospironolactone is S-methylated to 7α-thiomethylspironolactone or undergoes an elimination reaction to canrenone.2,3 7α-thiomethylspironolactone is reduced to 3α-hydroxythiomethylspironolactone or 3β-hydroxythiomethylspironolactone.2,3

Canrenone was originally thought to be the primary circulating metabolite, however more recent studies have demonstrated that the primary metabolite is actually 7α-thiomethylspironolactone.8,9

Route of elimination

Metabolites of spironolactone are excreted 42-56% in urine, and 14.2-14.6% in the feces.6 No unmetabolized spironolactone is present in the urine.6

Half life

1.4 hours.Label,7

Canrenone has a half life of 16.5 hours, 7-α-thiomethylspirolactone has a half life of 13.8 hours, and 6-ß-hydroxy-7-α-thiomethylspirolactone has a half life of 15 hours.Label,7

Clearance

Clearance data is not readily available.Label,7

Toxicity

Patients experiencing an overdose may present with drowsiness, mental confusion, maculopapular or erythematous rash, nausea, vomiting, dizziness, or diarrhea. Vomiting is generally induced or a gastric lavage is performed.Label Supportive treatment involves maintining hydration, electrolyte balance, and vital functionsLabel.

The oral LD50 in mice, rats, and rabbits is >1g/kg.Label

Spironolactone should be avoided in pregnancy due to reports of feminization of male fetuses in animal studies.Label Active metabolites of spironolactone are present in breast milk and levels that are likely inconsequential, though the long term effects have not been studied.Label

In animal studies, spironolactone slowed follicle development, ovulation, and implantation.Label Spironolactone increased the incidence of benign adenomas in the testes of male rats, benign uterine endometrial stromal polyps in female rats, and thyroid follicular cell adenomas in both sexes of rats.Label Spironolactone and canrenone are generally not considered to be mutagenic in tests but canrenone occasionally tests positive for mutagenicity with metabolic activation and spironolactone has occasionally tested inconclusive though slightly positive for mutagenicity.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Spironolactone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Spironolactone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Spironolactone.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Spironolactone.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Spironolactone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Spironolactone.
AbacavirSpironolactone may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AbediterolThe therapeutic efficacy of Abediterol can be decreased when used in combination with Spironolactone.
AbirateroneThe therapeutic efficacy of Abiraterone can be decreased when used in combination with Spironolactone.
AcarboseSpironolactone may increase the excretion rate of Acarbose which could result in a lower serum level and potentially a reduction in efficacy.
AcebutololThe risk or severity of hyperkalemia can be increased when Spironolactone is combined with Acebutolol.
Additional Data Available
  • Extended Description
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  • Severity
    Severity

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Food Interactions
  • Avoid alcohol.
  • Food increases the bioavailability of spironolactone by almost 100%.
  • Spironolactone may decrease the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.

References

Synthesis Reference

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

US4332721
General References
  1. 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. [PubMed:9144743]
  2. 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. [PubMed:3675606]
  3. 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. [PubMed:7895608]
  4. 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. [PubMed:22468178]
  5. Millington K, Liu E, Chan YM: The Utility of Potassium Monitoring in Gender-Diverse Adolescents Taking Spironolactone. J Endocr Soc. 2019 Apr 4;3(5):1031-1038. doi: 10.1210/js.2019-00030. eCollection 2019 May 1. [PubMed:31065620]
  6. Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. [PubMed:363379]
  7. 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. [PubMed:28024992]
  8. 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. [PubMed:15947888]
  9. 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. [PubMed:2723123]
  10. 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. [PubMed:15134800]
  11. 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. [PubMed:13608362]
  12. FDA Approved Drug Products: Spironolactone [Link]
  13. Aldactone® (spironolactone) FDA Label [Link]
External Links
Human Metabolome Database
HMDB0014565
KEGG Drug
D00443
KEGG Compound
C07310
PubChem Compound
5833
PubChem Substance
46508525
ChemSpider
5628
BindingDB
50228080
ChEBI
9241
ChEMBL
CHEMBL1393
Therapeutic Targets Database
DAP000297
PharmGKB
PA451483
Guide to Pharmacology
GtP Drug Page
HET
SNL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Spironolactone
ATC Codes
C03DA01 — Spironolactone
AHFS Codes
  • 24:32.20 — Mineralocorticoid (Aldosterone) Receptor Antagonists
PDB Entries
2ab2 / 2oax / 3vhu
FDA label
Download (204 KB)
MSDS
Download (72.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentPolycystic Ovaries Syndrome1
0Not Yet RecruitingTreatmentOvulatory Dysfunction / Polycystic Ovaries Syndrome / Puberty Disorders1
0RecruitingBasic ScienceHyperandrogenism / Polycystic Ovaries Syndrome / Puberty1
0RecruitingTreatmentAtrial Fibrillation (AF)1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHeart Failure1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentPulmonary Hypertension (PH)1
1Not Yet RecruitingDiagnosticCardiomyopathy With Unknown Etiology1
1Not Yet RecruitingTreatmentMelasma1
1RecruitingTreatmentHeart Failure1
1RecruitingTreatmentMuscular Dystrophy, Duchenne1
1TerminatedBasic ScienceType 2 Diabetic Nephropathy1
1, 2Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1, 2CompletedTreatmentCentral Serous Chorioretinitis1
1, 2Not Yet RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Relapsed Adult AML1
1, 2RecruitingOtherNASH - Nonalcoholic Steatohepatitis1
2Active Not RecruitingPreventionCardiovascular Disease (CVD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
2CompletedPreventionAcute Kidney Injury (AKI) / IHD / Prophylaxis of Contrast-induced nephropathy1
2CompletedPreventionCutaneous Atrophy Due to Corticosteroids1
2CompletedPreventionHeart Failure1
2CompletedSupportive CareAdvanced Malignant Neoplasm / Dermatologic Complication / Dermatologic Complications / Neoplasms, Malignant1
2CompletedTreatmentACTH / Cortisol Resistance / Glucocorticoid therapy / Mineralcorticoid / Negative Feedback1
2CompletedTreatmentAcanthosis Nigricans / Polycystic Ovaries Syndrome1
2CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD)1
2CompletedTreatmentChronic Kidney Disease (CKD) / High Blood Pressure (Hypertension) / Hyperkalemia1
2CompletedTreatmentCongenital Heart Disease (CHD) / Endomyocardial Fibrosis / Heart Failure1
2CompletedTreatmentDiabetes Mellitus (DM) / High Blood Pressure (Hypertension) / Kidney Diseases1
2CompletedTreatmentEnd Stage Renal Disease / Hemodialysis1
2CompletedTreatmentEnd-Stage Renal Disease (ESRD)1
2CompletedTreatmentFatty Liver / Steatohepatitis1
2CompletedTreatmentFemale Pattern Hair Loss1
2CompletedTreatmentHeart Failure2
2CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedTreatmentHyperkalemia / Resistant Hypertension1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentNeovascular Age-Related Macular Degeneration1
2CompletedTreatmentPuberty, Precocious1
2RecruitingTreatmentAlbuminuria / Chronic Kidney Disease (CKD)1
2RecruitingTreatmentEndothelial Dysfunction / Pulmonary Arterial Hypertension (PAH)1
2SuspendedTreatmentTransplant, Kidney1
2TerminatedTreatmentHigh Blood Pressure (Hypertension)1
2TerminatedTreatmentMalignancies1
2WithdrawnTreatmentAcute Heart Failure (AHF)1
2, 3Active Not RecruitingTreatmentLiver Cirrhosis / Refractory/Recurrent Ascites1
2, 3CompletedDiagnosticDiabetic Nephropathies / Retinopathy, Diabetic1
2, 3CompletedPreventionAtrial Fibrillation (AF)1
2, 3CompletedPreventionDiabetic Nephropathies / Glomerulonephritis / Kidney Diseases / Proteinuria1
2, 3CompletedTreatmentHeart Failure1
2, 3CompletedTreatmentPolycystic Ovarian Syndrome1
2, 3RecruitingPreventionCritically-ill Patients / Malignancies1
2, 3RecruitingTreatmentChronic Lung Disease of Prematurity / Chronic Lung Diseases1
3Active Not RecruitingTreatmentAtrial Fibrillation (AF)1
3Active Not RecruitingTreatmentHeart Failure / Impaired Glucose Tolerance / Type 2 Diabetes Mellitus1
3CompletedPreventionCalcifications, Vascular / Coronary Artery Calcifications1
3CompletedPreventionEnd Stage Renal Disease (ESRD)1
3CompletedPreventionHeart Failure1
3CompletedTreatmentArterial Hypertension / Diabetes Mellitus (DM) / Hypertension, Resistant to Conventional Therapy1
3CompletedTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD)1
3CompletedTreatmentCardiovascular Disease (CVD) / Congestive Heart Failure / Heart Diseases1
3CompletedTreatmentCongestive Heart Failure / Diastolic Heart Failure1
3CompletedTreatmentDuchenne's Muscular Dystrophy (DMD)1
3CompletedTreatmentHeart Failure1
3CompletedTreatmentHypertension,Essential1
3CompletedTreatmentMyocardial Infarction1
3Not Yet RecruitingPreventionAcute Kidney Injury (AKI)1
3RecruitingPreventionEndstage Renal Disease1
3RecruitingTreatmentAcne Vulgaris1
3RecruitingTreatmentAldosterone Blockade / Atrial Fibrillation (AF) / Surgery, Cardiac1
3RecruitingTreatmentEnd Stage Renal Failure on Dialysis1
3RecruitingTreatmentHeart Failure With Preserved Ejection Fraction (HFpEF)1
3RecruitingTreatmentST Elevation Myocardial Infarction1
4Active Not RecruitingBasic ScienceHealthy Volunteers / Hypoglycemia1
4Active Not RecruitingTreatmentAtrial Fibrillation (AF)1
4Active Not RecruitingTreatmentCardio-Renal Syndrome / Renal Insufficiency,Chronic1
4Active Not RecruitingTreatmentHypertension, Resistant to Conventional Therapy1
4CompletedDiagnosticHeart Failure1
4CompletedDiagnosticHeart Failure / Nonischemic Dilated Cardiomyopathy1
4CompletedPreventionAnthracycline Induced Cardiotoxicity1
4CompletedPreventionEnd-stage Renal Failure (ESRF)1
4CompletedTreatmentArterial Elasticity / Arterial Stiffness1
4CompletedTreatmentAscites / Liver Cirrhosis1
4CompletedTreatmentChronic Renal Failure (CRF)1
4CompletedTreatmentDiabetes Mellitus (DM) / Hypertension, Resistant to Conventional Therapy1
4CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetic Nephropathies1
4CompletedTreatmentDiastolic Heart Failure1
4CompletedTreatmentHeart Failure1
4CompletedTreatmentHeart Failure / Ventricular Dysfunction, Left1
4CompletedTreatmentHigh Blood Pressure (Hypertension)3
4CompletedTreatmentHypertension Resistant To Conventional Therapy1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)1
4CompletedTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
4CompletedTreatmentStable Chronic Heart Failure2
4Enrolling by InvitationPreventionDisorder Related to Renal Transplantation1
4Not Yet RecruitingPreventionEnd Stage Renal Disease (ESRD) / Peritoneal dialysis therapy1
4Not Yet RecruitingTreatmentFibrosis / Hypertrophic Cardiomyopathy1
4Not Yet RecruitingTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
4Not Yet RecruitingTreatmentHidradenitis Suppurativa (HS)1
4RecruitingPreventionBlood Pressures / High Blood Pressure (Hypertension) / Stroke1
4RecruitingTreatmentAtherosclerosis1
4RecruitingTreatmentCardiomyopathy Right Ventricular / Chronic Right-Sided Heart Failure / Pulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension, Primary, 2 / Pulmonary Hypertension, Primary, 3 / Pulmonary Hypertension, Primary, 41
4RecruitingTreatmentHyperkalemia / Type2 Diabetes1
4RecruitingTreatmentLiver Cirrhosis / Portal Hypertension1
4RecruitingTreatmentPulmonary Hypertension (PH)1
4RecruitingTreatmentTransplantation, Liver1
4SuspendedTreatmentAlcohol Dependence / Cardiomyopathy, Alcoholic1
4TerminatedOtherPulmonary Arterial Hypertension (PAH)1
4TerminatedPreventionAlcoholic Cirrhosis1
4TerminatedPreventionPatients With Fungic Infections1
4Unknown StatusTreatmentChronic Renal Failure (CRF)1
4Unknown StatusTreatmentDiabetic Nephropathies1
4Unknown StatusTreatmentHeart Failure / Impaired Renal Function1
4Unknown StatusTreatmentHemodialysis Treatment1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)3
4Unknown StatusTreatmentHypertrophic Cardiomyopathy / Myocardial Fibrosis1
4Unknown StatusTreatmentLiver Cirrhosis / Portal Hypertension1
4Unknown StatusTreatmentRenal Failure1
4WithdrawnTreatmentCongestive Heart Failure / End Stage Renal Disease (ESRD)1
4WithdrawnTreatmentEnd Stage Renal Disease (ESRD) / Hemodialysis Treatment1
4WithdrawnTreatmentFemale Androgenetic Alopecia1
4WithdrawnTreatmentHeart Failure1
Not AvailableCompletedNot AvailableAcute Decompensated Heart Failure (ADHF)1
Not AvailableCompletedNot AvailableFractures, Bone / Type 2 Diabetes Mellitus1
Not AvailableCompletedDiagnosticCardiovascular Disease (CVD)1
Not AvailableCompletedPreventionBMI >30 kg/m2 / Insulin Resistance1
Not AvailableCompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases1
Not AvailableCompletedPreventionLong Qt Syndrome 1-2 / Sudden Cardiac Death1
Not AvailableCompletedTreatmentAtrial Fibrillation (AF) / Chronic Heart Failure (CHF)1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Proteinuria1
Not AvailableCompletedTreatmentCirrhosis, Decompensated1
Not AvailableCompletedTreatmentCongenital Disorders1
Not AvailableCompletedTreatmentCongestive Heart Failure1
Not AvailableCompletedTreatmentDiabetic Nephropathies1
Not AvailableCompletedTreatmentHyperaldosteronism / OSAS (Obstructive Sleep Apneas Syndrome) / Resistant Hypertension1
Not AvailableCompletedTreatmentHypertension,Essential1
Not AvailableCompletedTreatmentHypokalemia Caused by Thiazide Diuretics / Idiopathic Hypercalciuria1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentPolycystic Ovaries Syndrome2
Not AvailableCompletedTreatmentResistant Arterial Hypertension1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus / Vascular Diseases1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Cardiac Dysrhythmia / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infection / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headache / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperaldosteronism / Hyperlipidemias / Hypokalaemia / Hypotension / Infantile Hemangiomas / Infection caused by staphylococci / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Insomnia / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenia / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infection / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableAlport Syndrome / Familial Benign Hematuria / Hereditary Kidney Disease / Pediatric Kidney Disease / Thin Basement Membrane Disease1
Not AvailableRecruitingNot AvailablePrimary Aldosteronism / Primary Aldosteronism Due to Adrenal Hyperplasia (Bilateral) / Primary Aldosteronism Due to Aldosterone Producing Adenoma1
Not AvailableRecruitingBasic ScienceBMI >30 kg/m2 / Hyperandrogenemia / Polycystic Ovaries Syndrome1
Not AvailableRecruitingBasic SciencePrimary Aldosteronism1
Not AvailableRecruitingTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableTerminatedTreatmentCongestive Heart Failure1
Not AvailableUnknown StatusPreventionAcute Kidney Injury (AKI) / Acute Renal Injury1
Not AvailableUnknown StatusPreventionDiabetes Mellitus (DM) / Endocrine System Diseases / Glucose Metabolism Disorders / Metabolic Diseases1
Not AvailableUnknown StatusTreatmentAtrial Fibrillation (AF)1
Not AvailableUnknown StatusTreatmentLow-Renin Hypertension1
Not AvailableWithdrawnTreatmentCongestive Heart Failure2
Not AvailableWithdrawnTreatmentDiastolic Heart Failure1
Not AvailableWithdrawnTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableWithdrawnTreatmentPulmonary Hypertension (PH) / Right Heart Failure1

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
FormRouteStrength
TabletOral
SuspensionOral25 mg/5mL
GelTopical
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
TabletOral
Tablet, film coatedOral
Prices
Unit descriptionCostUnit
Spironolactone powder12.56USD g
Aldactone 100 mg tablet2.14USD tablet
Aldactazide 50-50 mg tablet2.02USD tablet
Aldactazide 50-50 tablet1.92USD tablet
Aldactone 50 mg tablet1.84USD tablet
Spironolactone 100 mg tablet1.45USD tablet
Aldactazide 25-25 mg tablet1.26USD tablet
Aldactazide 25-25 tablet1.04USD tablet
Spironolactone 50 mg tablet0.83USD tablet
Aldactone 25 mg tablet0.8USD tablet
Spironolactone-HCTZ 25-25 mg tablet0.57USD tablet
Spironolactone 25 mg tablet0.5USD tablet
Novo-Spiroton 100 mg Tablet0.25USD tablet
Novo-Spiroton 25 mg Tablet0.11USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9757394No2017-09-122036-10-28Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134.5 °C[MSDS]
boiling point (°C)201[MSDS]
logP2.78https://www.ncbi.nlm.nih.gov/pubmed/26642673
Predicted Properties
PropertyValueSource
Water Solubility0.00198 mg/mLALOGPS
logP3.1ALOGPS
logP3.64ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity113.5 m3·mol-1ChemAxon
Polarizability46.03 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9912
Blood Brain Barrier+0.932
Caco-2 permeable+0.5432
P-glycoprotein substrateSubstrate0.5691
P-glycoprotein inhibitor IInhibitor0.6807
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterNon-inhibitor0.727
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6638
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9276
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.9158
CarcinogenicityNon-carcinogens0.9288
BiodegradationNot ready biodegradable0.9696
Rat acute toxicity2.0150 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9427
hERG inhibition (predictor II)Non-inhibitor0.7002
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-9836000000-9f600bd39c3b914c0b17
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000900000-5e2e1944e45fcef225d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000900000-406c100eed5b6cdc3286

Taxonomy

Description
This compound belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Spironolactones and derivatives
Alternative Parents
3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Gamma butyrolactones / Tetrahydrofurans / Thioesters / Carboxylic acid esters / Carbothioic S-esters / Sulfenyl compounds / Oxacyclic compounds
show 3 more
Substituents
Spironolactone / 3-oxo-delta-4-steroid / 3-oxosteroid / Oxosteroid / Delta-4-steroid / Cyclohexenone / Gamma butyrolactone / Tetrahydrofuran / Carboxylic acid ester / Carbothioic s-ester
show 17 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
thioester, 3-oxo steroid, methyl ketone, oxaspiro compound, steroid lactone (CHEBI:9241) / Pregnane and derivatives [Fig] (C07310)

Targets

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
  1. Sitruk-Ware R: Progestogens in hormonal replacement therapy: new molecules, risks, and benefits. Menopause. 2002 Jan-Feb;9(1):6-15. [PubMed:11791081]
  2. 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. [PubMed:14664717]
  3. 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. [PubMed:14978157]
  4. Frishman WH, Stier CT Jr: Aldosterone and aldosterone antagonism in systemic hypertension. Curr Hypertens Rep. 2004 Jun;6(3):195-200. [PubMed:15128471]
  5. 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. [PubMed:15554912]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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. [PubMed:15947888]
  8. Rossi G, Boscaro M, Ronconi V, Funder JW: Aldosterone as a cardiovascular risk factor. Trends Endocrinol Metab. 2005 Apr;16(3):104-7. [PubMed:15808807]
Details
2. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
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
  1. 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. [PubMed:18819053]
Details
3. 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
  1. 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. [PubMed:20650892]
Details
4. 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
  1. 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. [PubMed:20650892]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
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
  1. 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. [PubMed:976190]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Steroid 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name
CYP17A1
Uniprot ID
P05093
Uniprot Name
Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight
57369.995 Da
References
  1. Authors unspecified: Spironolactone and endocrine dysfunction. Ann Intern Med. 1976 Nov;85(5):630-6. [PubMed:984618]
  2. Millington K, Liu E, Chan YM: The Utility of Potassium Monitoring in Gender-Diverse Adolescents Taking Spironolactone. J Endocr Soc. 2019 Apr 4;3(5):1031-1038. doi: 10.1210/js.2019-00030. eCollection 2019 May 1. [PubMed:31065620]
  3. Desai; Meena P.; Vijayalakshmi Bhatia & P.S.N. Menon (2001). Pediatric Endocrine Disorders. Orient Blackswan. [ISBN:978-81-250-2025-7]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...

Components:
References
  1. Corvol P, Michaud A, Menard J, Freifeld M, Mahoudeau J: Antiandrogenic effect of spirolactones: mechanism of action. Endocrinology. 1975 Jul;97(1):52-8. [PubMed:166833]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Braunstein GD: Clinical practice. Gynecomastia. N Engl J Med. 2007 Sep 20;357(12):1229-37. [PubMed:17881754]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only...

Components:
NameUniProt ID
Voltage-dependent calcium channel gamma-1 subunitQ06432
Voltage-dependent calcium channel gamma-2 subunitQ9Y698
Voltage-dependent calcium channel gamma-3 subunitO60359
Voltage-dependent calcium channel gamma-4 subunitQ9UBN1
Voltage-dependent calcium channel gamma-5 subunitQ9UF02
Voltage-dependent calcium channel gamma-6 subunitQ9BXT2
Voltage-dependent calcium channel gamma-7 subunitP62955
Voltage-dependent calcium channel gamma-8 subunitQ8WXS5
Voltage-dependent calcium channel subunit alpha-2/delta-1P54289
Voltage-dependent calcium channel subunit alpha-2/delta-2Q9NY47
Voltage-dependent calcium channel subunit alpha-2/delta-3Q8IZS8
Voltage-dependent calcium channel subunit alpha-2/delta-4Q7Z3S7
Voltage-dependent L-type calcium channel subunit alpha-1CQ13936
Voltage-dependent L-type calcium channel subunit alpha-1DQ01668
Voltage-dependent L-type calcium channel subunit alpha-1FO60840
Voltage-dependent L-type calcium channel subunit alpha-1SQ13698
Voltage-dependent L-type calcium channel subunit beta-1Q02641
Voltage-dependent L-type calcium channel subunit beta-2Q08289
Voltage-dependent L-type calcium channel subunit beta-3P54284
Voltage-dependent L-type calcium channel subunit beta-4O00305
Voltage-dependent N-type calcium channel subunit alpha-1BQ00975
Voltage-dependent P/Q-type calcium channel subunit alpha-1AO00555
Voltage-dependent R-type calcium channel subunit alpha-1EQ15878
Voltage-dependent T-type calcium channel subunit alpha-1GO43497
Voltage-dependent T-type calcium channel subunit alpha-1HO95180
Voltage-dependent T-type calcium channel subunit alpha-1IQ9P0X4
References
  1. 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. [PubMed:10942165]
  2. Melander A, Danielson K, Schersten B, Thulin T, Wahlin E: Enhancement by food of canrenone bioavailability from spironolactone. Clin Pharmacol Ther. 1977 Jul;22(1):100-3. [PubMed:872489]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [PubMed:16054614]

Enzymes

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
  1. 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. [PubMed:15601807]
  2. 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. [PubMed:26721703]
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
  1. 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. [PubMed:976190]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. 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. [PubMed:9144743]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
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:
References
  1. 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. [PubMed:9144743]

Transporters

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
  1. 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. [PubMed:12011477]
Details
2. 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
  1. 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. [PubMed:21459122]
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
  1. 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. [PubMed:8779893]
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
  1. 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. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2019 16:22