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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- 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
Target Actions Organism UGlucocorticoid receptor Not Available Humans UMineralocorticoid receptor agonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Aldosterone can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Aldosterone. Acarbose The risk or severity of hyperglycemia can be increased when Aldosterone is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Aldosterone is combined with Aceclofenac. Acemetacin The 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
- 11-Hydroxycorticosteroids
- Adrenal Cortex Hormones
- Corticosteroids
- Corticosteroids for Systemic Use
- Corticosteroids for Systemic Use, Plain
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hydroxycorticosteroids
- Immunosuppressive Agents
- Mineralocorticoids
- P-glycoprotein inducers
- P-glycoprotein substrates
- Pregnanes
- Pregnenediones
- Pregnenes
- Steroids
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- 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
- Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. [Article]
- External Links
- KEGG Compound
- C01780
- PubChem Compound
- 5839
- PubChem Substance
- 46505770
- ChemSpider
- 5633
- BindingDB
- 19214
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Hypertension / Stroke / Transient Ischemic Attack 1 4 Recruiting Treatment Cardiovascular Disease (CVD) / Diabetes Mellitus 1 4 Recruiting Treatment Glomerular Diseases / Idiopathic Membranous Nephropathy / Renal Dysfunction 1 4 Withdrawn Treatment Chronic Kidney Disease (CKD) / Hypertension 1 4 Withdrawn Treatment Hypertension 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 166.5 °C PhysProp water solubility 51.2 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.08 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.148 mg/mL ALOGPS logP 1.54 ALOGPS logP 1.06 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 13.82 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 91.67 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 96.79 m3·mol-1 Chemaxon Polarizability 38.82 Å3 Chemaxon Number of Rings 4 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 + 0.9943 Blood Brain Barrier + 0.921 Caco-2 permeable + 0.8527 P-glycoprotein substrate Substrate 0.7719 P-glycoprotein inhibitor I Non-inhibitor 0.738 P-glycoprotein inhibitor II Non-inhibitor 0.7441 Renal organic cation transporter Non-inhibitor 0.6832 CYP450 2C9 substrate Non-substrate 0.8059 CYP450 2D6 substrate Non-substrate 0.904 CYP450 3A4 substrate Substrate 0.7278 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9189 CYP450 2D6 inhibitor Non-inhibitor 0.9251 CYP450 2C19 inhibitor Non-inhibitor 0.9434 CYP450 3A4 inhibitor Non-inhibitor 0.8795 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8737 Ames test Non AMES toxic 0.9073 Carcinogenicity Non-carcinogens 0.9543 Biodegradation Not ready biodegradable 0.9279 Rat acute toxicity 1.5456 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9242 hERG inhibition (predictor II) Non-inhibitor 0.5136
Spectra
- Mass Spec (NIST)
- Download (12.2 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.9369006 predictedDarkChem Lite v0.1.0 [M-H]- 198.2971006 predictedDarkChem Lite v0.1.0 [M-H]- 198.5964006 predictedDarkChem Lite v0.1.0 [M-H]- 190.85399 predictedDeepCCS 1.0 (2019) [M+H]+ 198.4339006 predictedDarkChem Lite v0.1.0 [M+H]+ 198.3471006 predictedDarkChem Lite v0.1.0 [M+H]+ 197.7584006 predictedDarkChem Lite v0.1.0 [M+H]+ 192.74937 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.3232006 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.9851006 predictedDarkChem Lite v0.1.0 [M+Na]+ 198.708 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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
- 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
- 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]
- 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
- SubstrateInducer
- 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
- 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]
- 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
- 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
- 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]
- 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