Aldosterone

Title: Aldosterone
CAS Registry Number: 52-39-1
CAS Name: (11b)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al
Additional Names: 3,20-diketo-11b,18-oxido-4-pregnene-18,21-diol
Trademarks: Aldocorten (Novartis)
Molecular Formula: C21H28O5
Molecular Weight: 360.44
Percent Composition: C 69.98%, H 7.83%, O 22.19%
Literature References: Adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Isoln: Simpson et al., Experientia 9, 333 (1953); Helv. Chim. Acta 37, 1163 (1954); Mattox et al., J. Am. Chem. Soc. 75, 4869 (1953); Harman et al., ibid. 76, 5035 (1954). Solutions contain an equilibrium mixture of the aldehyde and the hemiacetal, the equilibrium favoring the latter. Structure: Tait et al., Experientia 10, 132 (1954); Helv. Chim. Acta 37, 1200 (1954). Crystal structure and molecular conformation: Duax, Hauptmann, J. Am. Chem. Soc. 94, 5467 (1972). 13C-NMR spectrum: P. Gerard, Org. Magn. Reson. 11, 478 (1978). Total synthesis: Schmidlin et al., Helv. Chim. Acta 40, 1438 (1957); Johnson et al., J. Am. Chem. Soc. 80, 2585 (1958); 85, 1409 (1963). Three-step synthesis from corticosterone: Barton, Beaton, ibid. 82, 2640 (1960); 83, 4083 (1961). Alternate synthesis: D. H. R. Barton et al., J. Chem. Soc. Perkin Trans. 1 1975, 2243; M. Miyano, J. Org. Chem. 46, 1846 (1981). Biosynthesized in the zona glomerulosa and transported chiefly by albumin. In man, 400 mg secreted normally in one day. Secretion influenced by ACTH, growth hormone, plasma sodium and potassium, and the renin-angiotensin system. Causes reabsorption of Na+, Cl-, and HCO3- and diuresis of K+. Review: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 701-720.
Properties: Hydrated crystals from dilute acetone, mp 108-112° (when anhydr mp 164°). [a]D23 +152.2° (anhydr; c = 2 in acetone). [a]D25 +161° (c = 0.1 in chloroform). uv max: 240 nm (log e 4.20 for the monohydrate; emol 15,000 for the anhydr).
Melting point: mp 108-112° (when anhydr mp 164°)
Optical Rotation: [a]D23 +152.2° (anhydr; c = 2 in acetone); [a]D25 +161° (c = 0.1 in chloroform)
Absorption maximum: uv max: 240 nm (log e 4.20 for the monohydrate; emol 15,000 for the anhydr)
Derivative Type: 21-Acetate
Molecular Formula: C23H30O6
Molecular Weight: 402.48
Percent Composition: C 68.64%, H 7.51%, O 23.85%
Literature References: Synthesis: Wettstein et al.; Jeger, US 3002972 and US 3014029 (both 1958 to Ciba).
Properties: Flat needles from acetone + ether, mp 198-199°. [a]D24 +121.7° (c = 0.71 in chloroform).
Melting point: mp 198-199°
Optical Rotation: [a]D24 +121.7° (c = 0.71 in chloroform)
Therap-Cat: Mineralocorticoid.
Therap-Cat-Vet: Mineralocorticoid.
Keywords: Mineralocorticoid.
Aldrin Alefacept Alemtuzumab Alendronic Acid Aleuritic Acid

Aldosterone
Aldosterone-2D-skeletal.svg
Identifiers
CAS number 52-39-1 YesY
PubChem 5839
ChemSpider 5633 YesY
UNII 4964P6T9RB YesY
DrugBank DB04630
KEGG C01780 YesY
MeSH Aldosterone
ChEBI CHEBI:27584 YesY
ChEMBL CHEMBL273453 YesY
ATC code H02AA01
Jmol-3D images Image 1
Properties
Molecular formula C21H28O5
Molar mass 360.44 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Aldosterone is a steroid hormone (mineralocorticoid family) produced by the outer section (zona glomerulosa) of the adrenal cortex in the adrenal gland.[1][2] It plays a central role in the regulation of blood pressure mainly by acting on the distal tubules and collecting ducts of the nephron, increasing reabsorption of ions and water in the kidney, to cause the conservation of sodium, secretion of potassium, increased water retention, and increased blood pressure.[1] When dysregulated, aldosterone is pathogenic and contributes to the development and progression of cardiovascular and renal disease.[2] Aldosterone has exactly the opposite function of the atrial natriuretic hormone secreted by the heart.[1]

Drugs that interfere with the secretion or action of aldosterone are in use as antihypertensives, like lisinopril, which lowers blood pressure by blocking the angiotensin-converting enzyme (ACE), leading to lower aldosterone secretion; its net effect is to reduce sodium and water retention but increase retention of potassium. Aldosterone is part of the renin-angiotensin system. Another example is spironolactone, a potassium-sparing diuretic, which decreases blood pressure by releasing fluid from the body while retaining potassium.

It was first isolated by Simpson and Tait in 1953.[3]