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Identification
NameAldosterone
Accession NumberDB04630
Typesmall molecule
Groupsexperimental
Description

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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-aldosteroneNot AvailableNot Available
11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-alNot AvailableNot Available
11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-alNot AvailableNot Available
11beta,21-dihydroxy-3,20-dioxo-4-pregnen-18-alNot AvailableNot Available
11beta,21-dihydroxy-3,20-dioxo-pregn-4-ene-18-alNot AvailableNot Available
11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-alNot AvailableNot Available
11beta,21-Dihydroxypregn-4-ene-3,18,20-trioneNot AvailableNot Available
18-AldocorticosteroneNot AvailableNot Available
18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dioneNot AvailableNot Available
18-OxocorticosteroneNot AvailableNot Available
AldocortenNot AvailableNot Available
AldocorteneNot AvailableNot Available
AldocortinNot AvailableNot Available
AldosteronaSpanishNot Available
AldosteronumLatinNot Available
D-aldosteroneNot AvailableNot Available
ElectrocortinNot AvailableNot Available
ElektrocortinNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number52-39-1
WeightAverage: 360.444
Monoisotopic: 360.193674006
Chemical FormulaC21H28O5
InChI KeyInChIKey=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,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-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
Mass Specshow(12.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Cyclohexanols; Ketones; Cyclic Alcohols and Derivatives; Primary Alcohols; Enolates; Polyamines; Aldehydes
Substituents3-keto-steroid; 11-hydroxy-steroid; 20-keto-steroid; cyclohexanol; cyclic alcohol; ketone; secondary alcohol; primary alcohol; enolate; polyamine; alcohol; carbonyl group; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsAt 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 actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Aldosterone
    Aldosterone 18-glucuronideDetails
    Aldosterone
      Tetrahydroaldosterone-3-glucuronideDetails
      Route of eliminationNot Available
      Half lifeNot Available
      ClearanceNot Available
      ToxicityNot Available
      Affected organisms
      • Humans and other mammals
      PathwaysNot Available
      SNP Mediated EffectsNot Available
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      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 substrate Non-inhibitor 0.9189
      CYP450 2D6 substrate Non-inhibitor 0.9251
      CYP450 2C19 substrate Non-inhibitor 0.9434
      CYP450 3A4 substrate 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
      Pharmacoeconomics
      ManufacturersNot Available
      PackagersNot Available
      Dosage formsNot Available
      PricesNot Available
      PatentsNot Available
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point166.5 °CPhysProp
      water solubility51.2 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
      logP1.08HANSCH,C ET AL. (1995)
      Predicted Properties
      PropertyValueSource
      water solubility1.48e-01 g/lALOGPS
      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 area91.67ChemAxon
      rotatable bond count3ChemAxon
      refractivity96.79ChemAxon
      polarizability38.87ChemAxon
      number of rings4ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterYesChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      SpectraNot Available
      References
      Synthesis Reference

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

      US5120724
      General Reference
      1. Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. Pubmed
      External Links
      ResourceLink
      KEGG CompoundC01780
      PubChem Compound5839
      PubChem Substance46505770
      ChemSpider5633
      ChEBI27584
      ChEMBL
      Therapeutic Targets DatabaseDAP001344
      PharmGKBPA164924487
      HETAS4
      WikipediaAldosterone
      ATC CodesH02AA01
      AHFS CodesNot Available
      PDB EntriesNot Available
      FDA labelNot Available
      MSDSshow(68.4 KB)
      Interactions
      Drug InteractionsNot Available
      Food InteractionsNot Available

      1. Mineralocorticoid receptor

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Components

      Name UniProt ID Details
      Mineralocorticoid receptor P08235 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed

      1. Cytochrome P450 11B1, mitochondrial

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 11B1, mitochondrial P15538 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      2. Cytochrome P450 11B2, mitochondrial

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 11B2, mitochondrial P19099 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      3. Steroid 17-alpha-hydroxylase/17,20 lyase

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inducer

      Components

      Name UniProt ID Details
      Steroid 17-alpha-hydroxylase/17,20 lyase P05093 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      1. Multidrug resistance protein 1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate inducer

      Components

      Name UniProt ID Details
      Multidrug resistance protein 1 P08183 Details

      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. Pubmed
      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. Pubmed

      2. Solute carrier family 22 member 5

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Solute carrier family 22 member 5 O76082 Details

      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. Pubmed

      3. Solute carrier organic anion transporter family member 1A2

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Solute carrier organic anion transporter family member 1A2 P46721 Details

      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
      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. Pubmed

      Comments
      Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25