Aldosterone

Identification

Generic Name
Aldosterone
DrugBank Accession Number
DB04630
Background

A hormone secreted by the adrenal cortex that regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 360.444
Monoisotopic: 360.193674006
Chemical Formula
C21H28O5
Synonyms
  • (+)-aldosterone
  • (11β)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al
  • 11beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al
  • 11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al
  • Aldosterona
  • Aldosterone
  • Aldosteronum

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

At the late distal tubule and collecting duct, aldosterone has two main actions: 1) aldosterone acts on mineralocorticoid receptors (MR) on principal cells in the distal tubule of the kidney nephron, increasing the permeability of their apical (luminal) membrane to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis leading to phosphorylation of the pump and a conformational change in the pump exposes the Na+ ions to the outside. The phosphorylated form of the pump has a low affinity for Na+ ions, hence reabsorbing sodium (Na+) ions and water into the blood, and secreting potassium (K+) ions into the urine; 2) aldosterone stimulates H+ secretion by intercalated cells in the collecting duct, regulating plasma bicarbonate (HCO3−) levels and its acid/base balance; and 3) aldosterone may act on the central nervous system via the posterior pituitary gland to release vasopressin (ADH) which serves to conserve water by direct actions on renal tubular resorption.

Mechanism of action
TargetActionsOrganism
UGlucocorticoid receptorNot AvailableHumans
UMineralocorticoid receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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
AbametapirThe serum concentration of Aldosterone can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Aldosterone.
AcarboseThe risk or severity of hyperglycemia can be increased when Aldosterone is combined with Acarbose.
AceclofenacThe risk or severity of gastrointestinal irritation can be increased when Aldosterone is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal irritation can be increased when Aldosterone is combined with Acemetacin.
Food Interactions
Not Available

Categories

ATC Codes
H02AA01 — Aldosterone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-4-steroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Alpha-hydroxy ketones / Secondary alcohols / Cyclic alcohols and derivatives / Primary alcohols
show 3 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 18-oxosteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aldehyde / Aliphatic homopolycyclic compound
show 16 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 11beta-hydroxy steroid, 20-oxo steroid, mineralocorticoid, 21-hydroxy steroid, C21-steroid hormone, 18-oxo steroid (CHEBI:27584) / Pregnane and derivatives [Fig], Mineralocorticoids (C01780) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030026)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4964P6T9RB
CAS number
52-39-1
InChI Key
PQSUYGKTWSAVDQ-ZVIOFETBSA-N
InChI
InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1
IUPAC Name
(1S,3aS,3bS,9aR,9bS,10S,11aR)-10-hydroxy-1-(2-hydroxyacetyl)-9a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-11a-carbaldehyde
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C=O)C(=O)CO

References

Synthesis Reference

Jack Fishman, Elliot Hahn, Gregory A. Smith, "Aldosterone biosynthesis inhibitor." U.S. Patent US5120724, issued December, 1969.

US5120724
General References
  1. Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. [Article]
KEGG Compound
C01780
PubChem Compound
5839
PubChem Substance
46505770
ChemSpider
5633
BindingDB
19214
RxNav
1312358
ChEBI
27584
ChEMBL
CHEMBL273453
ZINC
ZINC000003833824
Therapeutic Targets Database
DAP001344
PharmGKB
PA164924487
PDBe Ligand
AS4
Wikipedia
Aldosterone
PDB Entries
2aa2 / 2q1h / 6hgj
MSDS
Download (68.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionHypertension / Stroke / Transient Ischemic Attack1
4RecruitingTreatmentCardiovascular Disease (CVD) / Diabetes Mellitus1
4RecruitingTreatmentGlomerular Diseases / Glomerulonephritis / Idiopathic Membranous Nephropathy1
4WithdrawnTreatmentChronic Kidney Disease (CKD) / Hypertension1
4WithdrawnTreatmentHypertension1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)166.5 °CPhysProp
water solubility51.2 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.08HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.148 mg/mLALOGPS
logP1.54ALOGPS
logP1.06Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.82Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area91.67 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity96.79 m3·mol-1Chemaxon
Polarizability38.82 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier+0.921
Caco-2 permeable+0.8527
P-glycoprotein substrateSubstrate0.7719
P-glycoprotein inhibitor INon-inhibitor0.738
P-glycoprotein inhibitor IINon-inhibitor0.7441
Renal organic cation transporterNon-inhibitor0.6832
CYP450 2C9 substrateNon-substrate0.8059
CYP450 2D6 substrateNon-substrate0.904
CYP450 3A4 substrateSubstrate0.7278
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9189
CYP450 2D6 inhibitorNon-inhibitor0.9251
CYP450 2C19 inhibitorNon-inhibitor0.9434
CYP450 3A4 inhibitorNon-inhibitor0.8795
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8737
Ames testNon AMES toxic0.9073
CarcinogenicityNon-carcinogens0.9543
BiodegradationNot ready biodegradable0.9279
Rat acute toxicity1.5456 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9242
hERG inhibition (predictor II)Non-inhibitor0.5136
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (12.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-06si-0694000000-60e1d35ad11d153b5152
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0596-2961000000-38453356e63a34116d1e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0596-2961000000-38453356e63a34116d1e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0009000000-107b6017ccfe71c7654f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-0009000000-1bac18c7fe8bbdc87eda
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02bf-0119000000-155b41e9cb849e7889e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-6059000000-985f2907adbf77c586c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2094000000-f3e3d12b7bd28ce3958f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0900-0941000000-44f73a57b91be126383b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-196.9369006
predicted
DarkChem Lite v0.1.0
[M-H]-198.2971006
predicted
DarkChem Lite v0.1.0
[M-H]-198.5964006
predicted
DarkChem Lite v0.1.0
[M-H]-190.85399
predicted
DeepCCS 1.0 (2019)
[M+H]+198.4339006
predicted
DarkChem Lite v0.1.0
[M+H]+198.3471006
predicted
DarkChem Lite v0.1.0
[M+H]+197.7584006
predicted
DarkChem Lite v0.1.0
[M+H]+192.74937
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.3232006
predicted
DarkChem Lite v0.1.0
[M+Na]+197.9851006
predicted
DarkChem Lite v0.1.0
[M+Na]+198.708
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Wilson VS, Bobseine K, Lambright CR, Gray LE Jr: A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists. Toxicol Sci. 2002 Mar;66(1):69-81. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
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. Bruner KL, Derfoul A, Robertson NM, Guerriero G, Fernandes-Alnemri T, Alnemri ES, Litwack G: The unliganded mineralocorticoid receptor is associated with heat shock proteins 70 and 90 and the immunophilin FKBP-52. Recept Signal Transduct. 1997;7(2):85-98. [Article]
  2. Bunda S, Liu P, Wang Y, Liu K, Hinek A: Aldosterone induces elastin production in cardiac fibroblasts through activation of insulin-like growth factor-I receptors in a mineralocorticoid receptor-independent manner. Am J Pathol. 2007 Sep;171(3):809-19. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  4. Bergann T, Ploger S, Fromm A, Zeissig S, Borden SA, Fromm M, Schulzke JD: A colonic mineralocorticoid receptor cell model expressing epithelial Na+ channels. Biochem Biophys Res Commun. 2009 May 1;382(2):280-5. doi: 10.1016/j.bbrc.2009.03.006. Epub 2009 Mar 9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Fallo F, Pezzi V, Barzon L, Mulatero P, Veglio F, Sonino N, Mathis JM: Quantitative assessment of CYP11B1 and CYP11B2 expression in aldosterone-producing adenomas. Eur J Endocrinol. 2002 Dec;147(6):795-802. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Fallo F, Pezzi V, Barzon L, Mulatero P, Veglio F, Sonino N, Mathis JM: Quantitative assessment of CYP11B1 and CYP11B2 expression in aldosterone-producing adenomas. Eur J Endocrinol. 2002 Dec;147(6):795-802. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
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. Takeda Y, Yoneda T, Demura M, Furukawa K, Koshida H, Miyamori I, Mabuchi H: Genetic analysis of the cytochrome P-450c17alpha (CYP17) and aldosterone synthase (CYP11B2) in Japanese patients with 17alpha-hydroxylase deficiency. Clin Endocrinol (Oxf). 2001 Jun;54(6):751-8. doi: 10.1046/j.1365-2265.2001.01272.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Torimoto N, Ishii I, Hata M, Nakamura H, Imada H, Ariyoshi N, Ohmori S, Igarashi T, Kitada M: Direct interaction between substrates and endogenous steroids in the active site may change the activity of cytochrome P450 3A4. Biochemistry. 2003 Dec 30;42(51):15068-77. doi: 10.1021/bi034409n. [Article]
  2. Maron BA, Leopold JA: Aldosterone receptor antagonists: effective but often forgotten. Circulation. 2010 Feb 23;121(7):934-9. doi: 10.1161/CIRCULATIONAHA.109.895235. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [Article]
  2. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
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. [Article]
  2. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [Article]

Drug created at September 11, 2007 17:49 / Updated at May 03, 2022 17:57