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(+)-Aldosterone

(+)-Aldosterone structure

CAS No:
52-39-1
Formula:
C21H28O5
Chemical Name:
(+)-Aldosterone
Synonyms:
Pregn-4-en-18-al,11,21-dihydroxy-3,20-dioxo-,(11β)-;Aldosterone;(11β)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al;Aldocorten;Aldocortene;(+)-Aldosterone;d-Aldosterone;11β,21-Dihydroxy-3,20-diketo-4-pregnen-18-al;11β,21-Dihydroxy-3,20-diketopregn-4-ene-18-al;11β,21-Dihydroxypregn-4-ene-3,18,20-trione;Electrocortin;Elektrocortin;18-Formyl-11β,21-dihydroxy-4-pregnene-3,20-dione;18-Oxocorticosterone;Aldocortin;Reichstein X;NSC 73856;152-04-5;10328-70-8;47468-70-2
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Aldosterone is the primary mineralocorticoid. Aldosterone is a steroid hormone, and it is synthesized and secreted in response to renin-angiotensin system activation (RAS) or high dietary potassium by the zona glomerulosa (ZG) of the adrenal cortex. Aldosterone activity is dependent by the binding and activation of the cytoplasmic/nuclear mineralocorticoid receptor (MR) at cellular level[1][2].

Solid

Aldosterone is a pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, increased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney. It has a role as a human metabolite and a mouse metabolite. It is an 11beta-hydroxy steroid, a 21-hydroxy steroid, a 18-oxo steroid, a 20-oxo steroid, a C21-steroid hormone, a steroid aldehyde, a 3-oxo-Delta(4) steroid, a primary alpha-hydroxy ketone and a mineralocorticoid. It derives from a hydride of a pregnane.|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.|Aldosterone is a mineralocorticoid hormone produced by aldosterone synthase (CYP11B2) in the zona glomerulosa of the adrenal cortex. Aldosterone binds to mineralocorticoid receptors (MR; NR3C2) and MR-aldosterone complexes regulate the expression of genes involved in the retention of sodium, the secretion of potassium, and water reabsorption, all of which may result increased blood pressure.|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.

(+)-Aldosterone Basic Attributes

Molecular Weight：

360.44

Exact Mass：

360.44

EC Number：

200-139-9

UNII：

4964P6T9RB

NSC Number：

73856

DSSTox ID：

DTXSID7022419

NCI Thesaurus Code：

C219

ATC Code：

H - Systemic hormonal preparations, excl. sex hormones and insulins

HScode：

29372900

Characteristics

PSA：

91.7

XLogP3：

1.08

Appearance：

White Crystalline Powder

Density：

1.3±0.1 g/cm3

Melting Point：

166.5 °C

Boiling Point：

568.1±50.0 °C at 760 mmHg

Flash Point：

2℃

Refractive Index：

1.586

Water Solubility：

51.18mg/L(37 ºC)

Storage Conditions：

2-8°C

Flammability characteristics：

Flammable; burning emissions stimulate smoke

Specific rotation：

D23 +152.2° (anhydr; c = 2 in acetone); D25 +161° (c = 0.1 in chloroform)

Collision Cross Section：

187.7 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|181.09 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|196.05 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|204.09 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]|188.31 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|187.7 Å² [M-H]-

Safety Information

Transport codes：

UN 1648 3 / PGII

wgk germany：

hazard class code：

36/37/38-36-20/21/22-11

safety instructions：

22-24/25-36-26-36/37-16

RTECS Number：

TU4523000

Marks：

Xi,Xn,F

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from food additives

Precautionary statement(s)：

P210-P280-P305 + P351 + P338

Hazard Statements：

H225-H302 + H312 + H332-H319

Drug Information

Pharmacology：

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.

MeSH Entry Terms：

Aldosterone

(+)-Aldosterone Use and Manufacturing

Uses

Imatinib intermediate

Manufacturing Info：

Pregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11.beta.)-: ACTIVE

Use Classification：

Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Computed Properties

Molecular Weight:360.4
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:360.19367399
Monoisotopic Mass:360.19367399
Topological Polar Surface Area:91.7
Heavy Atom Count:26
Complexity:682
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes