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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30O6
Molecular Weight 402.4807
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALDOSTERONE ACETATE

SMILES

[H][C@@]12CC[C@H](C(=O)COC(C)=O)[C@]1(C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C)C=O

InChI

InChIKey=HCJKXXMOOMBBPY-IEJDVFFQSA-N
InChI=1S/C23H30O6/c1-13(25)29-11-20(28)18-6-5-17-16-4-3-14-9-15(26)7-8-22(14,2)21(16)19(27)10-23(17,18)12-24/h9,12,16-19,21,27H,3-8,10-11H2,1-2H3/t16-,17-,18+,19-,21+,22-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H30O6
Molecular Weight 402.4807
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Aldosterone is 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. Recent findings have shown that the physiological functions of the hormone aldosterone go far beyond its well-known role in blood-pressure regulation and salt/water homeostasis. Aldosterone is for example involved in the regulation of inflammation, and also binds directly to mineralocorticoid receptors in specific brain regions. 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.

CNS Activity

Curator's Comment: Subchronic treatment with aldosterone induces depression-like behaviours and gene expression changes relevant to major depressive disorder in rodent models.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.8 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Metabolic alkalosis.
2001 Apr
Intrarenal angiotensin and bradykinin peptide levels in the remnant kidney model of renal insufficiency.
2001 Apr
Prolonged orexin administration stimulates steroid-hormone secretion, acting directly on the rat adrenal gland.
2001 Apr
Mineralocorticoid and glucocorticoid receptors inhibit UCP expression and function in brown adipocytes.
2001 Apr
Local inhibition of nitric oxide temporarily stimulates aldosterone secretion in conscious sheep in vivo.
2001 Apr
The serum- and glucocorticoid-induced kinase is a physiological mediator of aldosterone action.
2001 Apr
Regulation of calcitonin receptor by glucocorticoid in human osteoclast-like cells prepared in vitro using receptor activator of nuclear factor-kappaB ligand and macrophage colony-stimulating factor.
2001 Apr
Minireview: 11beta-hydroxysteroid dehydrogenase type 1- a tissue-specific amplifier of glucocorticoid action.
2001 Apr
Aldosterone induces rapid apical translocation of ENaC in early portion of renal collecting system: possible role of SGK.
2001 Apr
Additional beneficial effects of canrenoate in patients with anterior myocardial infarction on ACE-inhibitor treatment. A pilot study.
2001 Feb
Volume-induced natriuresis in healthy women: renal metabolism of prostacyclin and thromboxane, and physiological role of prostanoids.
2001 Feb
K(+) depletion and the progression of hypertensive disease or heart failure. The pathogenic role of diuretic-induced aldosterone secretion.
2001 Feb
Aldosterone receptor antagonism normalizes vascular function in liquorice-induced hypertension.
2001 Feb
Antifibrotic effects of N-acetyl-seryl-aspartyl-Lysyl-proline on the heart and kidney in aldosterone-salt hypertensive rats.
2001 Feb
Mineralocorticoid receptor affects AP-1 and nuclear factor-kappab activation in angiotensin II-induced cardiac injury.
2001 Feb
C825T polymorphism of the G protein beta(3)-subunit and antihypertensive response to a thiazide diuretic.
2001 Feb
Workshop: mechanisms and cardiovascular damage in hypertension.
2001 Feb
Effect of furosemide on renal excretion of oxypurinol and purine bases.
2001 Feb
Prevention of aortic and cardiac fibrosis by spironolactone in old normotensive rats.
2001 Feb
Multiple aspects of mineralocorticoid selectivity.
2001 Feb
alpha1H T-type Ca2+ channel is the predominant subtype expressed in bovine and rat zona glomerulosa.
2001 Feb
Steroids differentially inhibit the nicotinic acetylcholine receptor.
2001 Feb 12
Lack of toxic effects of F 12511, a novel potent inhibitor of acyl-coenzyme A: cholesterol O-acyltransferase, on human adrenocortical cells in culture.
2001 Feb 15
Molecular mechanisms of human hypertension.
2001 Feb 23
Differential effects of agonists of aldosterone secretion on steroidogenic acute regulatory phosphorylation.
2001 Feb 28
[Effect of aldosterone antagonism in heart failure: pharmacotherapeutic options].
2001 Feb 3
Renal function, sodium and water homeostasis in patients with idiopathic extrahepatic portal vein thrombosis compared with normal healthy controls.
2001 Jan
Tackling polycystic ovary syndrome.
2001 Jan
Preformulation experiences and in vitro model studies with spironolactone-containing suppositories.
2001 Jan
Diagnosis and management of congenital adrenal hyperplasia: clinical, molecular and prenatal aspects.
2001 Jan-Feb
Slowing the progression of CHF. Drug therapy to correct neurohormonal abnormalities.
2001 Mar
Nesiritide for the treatment of decompensated heart failure.
2001 Mar
Effect of chronic oral administration of a low dose of captopril on sodium appetite of hypothyroid rats. Influence of aldosterone treatment.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Modulation of transalveolar fluid absorption by endogenous aldosterone in adult rats.
2001 Mar
Pathogenesis and management of sodium and water retention in cardiac failure and cirrhosis.
2001 Mar
Adverse cardiac effects of salt with fludrocortisone in hypertension.
2001 Mar
Arterial pressure, left ventricular mass, and aldosterone in essential hypertension.
2001 Mar
Water metabolism disturbances at different stages of primary thyroid failure.
2001 Mar
Comparison of sympathetic modulation induced by single oral doses of mibefradil, amlodipine, and nifedipine in healthy volunteers.
2001 Mar
A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension.
2001 Mar
Endocrine activities of ghrelin, a natural growth hormone secretagogue (GHS), in humans: comparison and interactions with hexarelin, a nonnatural peptidyl GHS, and GH-releasing hormone.
2001 Mar
Comparison of adrenal vein sampling and computed tomography in the differentiation of primary aldosteronism.
2001 Mar
Approach to the patient with hypertension, unexplained hypokalemia, and metabolic alkalosis.
2001 Mar
Salt intake and body fluid volumes: have we learned all there is to know?
2001 Mar
Two sporadic cases of Liddle's syndrome caused by De novo ENaC mutations.
2001 Mar
Inhibition of aldosterone production in rat adrenal mitochondria by 18-ethynyl-11-deoxycorticosterone: a simple model for kinetic interpretation of mechanism-based inhibitors.
2001 Mar
The release of antidiuretic hormone is appropriate in response to hypovolemia and/or sodium administration in children with severe head injury: a trial of lactated Ringer's solution versus hypertonic saline.
2001 Mar
Non-genomic actions of aldosterone: role in hypertension.
2001 Mar
Effect of therapeutic ultrasound on partition and diffusion coefficients in human stratum corneum.
2001 Mar 12
Patents

Sample Use Guides

Horses: Aldosterone was injected intravenously for 6 h at 20-min intervals (total 5.4 ug/kg body wt).
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: Cultured neonatal rat ventricular cardiomyocytes were stimulated in vitro with 1 umol/L aldosterone for 24 h. Aldosterone modulates the expression of cardiac voltage-operated Ca2+ channels and accelerates beating in cultured neonatal rat ventricular myocytes. v
Aldosterone within the concentration range of 0.01-1.0 umol/L stimulates the proliferation and osteogenic gene expressions and enhances α-ENaC gene expression in rat osteoblasts in vitro, suggesting the possibility that ENaC participates in aldosterone-mediated regulation of osteoblast functions.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:05 GMT 2023
Record UNII
RH7JOB7P70
Record Status Validated (UNII)
Record Version
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Name Type Language
ALDOSTERONE ACETATE
Common Name English
ALDO A
Common Name English
NSC-73857
Code English
D-ALDOSTERONE 21-ACETATE
Common Name English
ALDOSTERONE ACETATE, D-
Common Name English
ALDOSTERONE, 21-ACETATE
Systematic Name English
PREGN-4-EN-18-AL, 21-(ACETYLOXY)-11-HYDROXY-3,20-DIOXO-, (11.BETA.)-
Systematic Name English
ALDOSTERONE MONOACETATE
Common Name English
Code System Code Type Description
NSC
73857
Created by admin on Fri Dec 15 15:20:06 GMT 2023 , Edited by admin on Fri Dec 15 15:20:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID701043375
Created by admin on Fri Dec 15 15:20:06 GMT 2023 , Edited by admin on Fri Dec 15 15:20:06 GMT 2023
PRIMARY
CAS
297-91-6
Created by admin on Fri Dec 15 15:20:06 GMT 2023 , Edited by admin on Fri Dec 15 15:20:06 GMT 2023
PRIMARY
FDA UNII
RH7JOB7P70
Created by admin on Fri Dec 15 15:20:06 GMT 2023 , Edited by admin on Fri Dec 15 15:20:06 GMT 2023
PRIMARY
PUBCHEM
101637
Created by admin on Fri Dec 15 15:20:06 GMT 2023 , Edited by admin on Fri Dec 15 15:20:06 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY