ContaminantDB: Spironolactone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (15)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:55 UTC

Update Date

2026-03-26 18:31:18 UTC

Accession Number

CHEM003710

Identification

Common Name

Spironolactone

Class

Small Molecule

Description

A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827)

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Diuretic
Drug
Ester
Ether
Metabolite
Mineralocorticoid Receptor Antagonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Espironolactona	ChEBI
Spironolactonum	ChEBI
Spironolattone	ChEBI
Aldactone	Kegg
Aldactone a	HMDB
Aquareduct	HMDB
Espironolactona mundogen	HMDB
Frumikal	HMDB
Generosan brand OF spironolactone	HMDB
Merck dura brand OF spironolactone	HMDB
Mundogen brand OF spironolactone	HMDB
Spiro l.u.t.	HMDB
Spirobeta	HMDB
Spironone	HMDB
Wörwag brand OF spironolactone	HMDB
CT-Arzneimittel brand OF spironolactone	HMDB
Duraspiron	HMDB
Ashbourne brand OF spironolactone	HMDB
Azupharma brand OF spironolactone	HMDB
Flumach	HMDB
Pfizer brand OF spironolactone	HMDB
Practon	HMDB
Spirono-isis	HMDB
Betapharm brand OF spironolactone	HMDB
Spiro von CT	HMDB
Alphapharm brand OF spironolactone	HMDB
Alpharma brand OF spironolactone	HMDB
Alter brand OF spironolactone	HMDB
Hormosan brand OF spironolactone	HMDB
Jenaspiron	HMDB
Mayoly-spindler brand OF spironolactone	HMDB
Novo-spiroton	HMDB
Roche brand OF spironolactone	HMDB
Spiractin	HMDB
Spirogamma	HMDB
Spirolactone	HMDB
Spirono isis	HMDB
CT Arzneimittel brand OF spironolactone	HMDB
Cardel brand OF spironolactone	HMDB
Dexo brand OF spironolactone	HMDB
Espironolactona alter	HMDB
Jenapharm brand OF spironolactone	HMDB
Novo spiroton	HMDB
NovoSpiroton	HMDB
Novopharm brand OF spironolactone	HMDB
Pharmafrid brand OF spironolactone	HMDB
Searle brand OF spironolactone	HMDB
Spirolang	HMDB
Spirospare	HMDB
Veroshpiron	HMDB
Verospiron	HMDB
Verospirone	HMDB
Von CT, spiro	HMDB
CT, Spiro von	HMDB

Chemical Formula

C₂₄H₃₂O₄S

Average Molecular Mass

416.573 g/mol

Monoisotopic Mass

416.202 g/mol

CAS Registry Number

52-01-7

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

Traditional Name

spironolactone

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

InChI Identifier

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

InChI Key

LXMSZDCAJNLERA-ZHYRCANASA-N

Chemical Taxonomy

Description

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

Substituents

Spironolactone
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Carbothioic s-ester
Cyclic ketone
Thiocarboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organosulfur compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

thioester (CHEBI:9241 )
3-oxo steroid (CHEBI:9241 )
methyl ketone (CHEBI:9241 )
oxaspiro compound (CHEBI:9241 )
steroid lactone (CHEBI:9241 )
Pregnane and derivatives [Fig] (C07310 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Spironolactone Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	134.5°C
Boiling Point	Not Available
Solubility	22 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.64	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	18.01	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h2u-0109000000-b5dcae38bb499eaabba7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0000900000-5e2e1944e45fcef225d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0000900000-406c100eed5b6cdc3286	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0000900000-406c100eed5b6cdc3286	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0000900000-5e2e1944e45fcef225d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-0009200000-27849e6f24a460d7ac90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mn-0129000000-5819587c9e746750f5c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01tl-0192000000-6a35fab760c0aa732723	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-0009200000-defcf21ed513948675a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1009000000-ebe97ba9dd52376b449f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9004000000-2eccefa334bd23b4cdc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0002900000-f73d8e9df6c71e49d6eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uy1-0569200000-db11732abcc12259a54d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ukc-4593000000-33eba50454259079f605	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0001900000-329d630008c4558a5ec5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-7009500000-69af52e904d20a0c7b9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-8009000000-ba8deb5a673f3bd4868e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9836000000-9f600bd39c3b914c0b17	Spectrum

Toxicity Profile

Route of Exposure

Fairly rapidly absorbed from the gastrointestinal tract. Food increases the bioavailability of unmetabolized spironolactone by almost 100%.

Mechanism of Toxicity

Spironolactone is a specific pharmacologic antagonist of aldosterone, acting primarily through competitive binding of 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 which act more proximally in the renal tubule. Aldosterone interacts with a cytoplasmic mineralocorticoid receptor to enhance the expression of the Na+, K+-ATPase and the Na+ channel involved in a Na+ K+ transport in the distal tubule . Spironolactone bind to this mineralcorticoid receptor, blocking the actions of aldosterone on gene expression. Aldosterone is a hormone; its primary function is to retain sodium and excrete potassium in the kidneys.

Metabolism

Rapidly and extensively metabolized. The metabolic pathway of spironolactone is complex and can be divided into two main routes: those in which the sulfur moiety is retained and those in which the sulfur moiety is removed by dethioacetylation. Spironolactone is transformed to a reactive metabolite that can inactivate adrenal and testicular cytochrome P450 enzymes. It also has anti-androgenic activity. Route of Elimination: The metabolites are excreted primarily in the urine and secondarily in bile. Half Life: 10 minutes

Toxicity Values

The oral LD₅₀ of spironolactone is greater than 1,000 mg/kg in mice, rats, and rabbits.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (4)

Uses/Sources

Used primarily to treat low-renin hypertension, hypokalemia, and Conn's syndrome.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Acute overdosage of spironolactone may be manifested by drowsiness, mental confusion, maculopapular or erythematous rash, nausea, vomiting, dizziness, or diarrhea. Spironolactone has been shown to be a tumorigen in chronic toxicity studies in rats.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00421

HMDB ID

HMDB0014565

FooDB ID

FDB006238

Phenol Explorer ID