Grundinformationen
- CAS
52-39-1- Standard-SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C=O)[C@@H](C(=O)CO)CC[C@@H]12- InChIKey
PQSUYGKTWSAVDQ-ZVIOFETBSA-N- Summenformel
- C21H28O5
- Durchschnittliche Molmasse
- 360,4 g/mol
- Monoisotopische Masse
- 360,193674
Überblick
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 mouse metabolite and a human metabolite. It is a steroid aldehyde, a primary alpha-hydroxy ketone, a mineralocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 18-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.
Namen und Bezeichner
- Bevorzugter Name
- Aldosterone
- IUPAC
- (8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehyde
- Lokaler Name
- Aldosteron
- Englischer Name
- ALDOSTERONE
- Summenformel
- C21H28O5
- Molmasse
- 360.44
Namen und Synonyme
ALDOSTERONE52-39-1(+)-AldosteroneAldosteronaAldosteronum11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al11beta,21-Dihydroxypregn-4-ene-3,18,20-trione(11BETA)-11,21-DIHYDROXY-3,20-DIOXOPREGN-4-EN-18-AL11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehydeNSC-7385611beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al
Weitere Namen anzeigen
ReichsteinREICHSTEIN XLECTROCORTINALDOSTERONE(RG)Aldosterone-[2,2,4,6,6,17,21,21-2H7]4-PREGNEN-11-BETA, 21-DIOL-3,18,20-TRIONEμ100 97% (CP)ALD ELISA
11beta,21-dihydroxy-3,20-dioxo-pregn-4-ene-18-al4964P6T9RBDTXSID7022419CHEBI:27584NSC73856(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthrene-13-carbaldehydeRefChem:553942DTXCID902419
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,1
- Polarare Oberfläche (TPSA)
- 91,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 682
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Steroids
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
LogP
1.08
1.08
Solubility0.0512 mg/mL at 37 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point166.5 °C
Physical DescriptionSolid
Collision Cross Section
188.31 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
181.09 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
202.8 Ų [M+Na]+
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 22-24-25
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29372900
- RTECS-Nr.
- TU4523000
- risk_code
- 36/37/38-36-20/21/22-11
- hazard_code
- Xi,Xn,F
- safety_code
- 22-24/25-36-26-36/37-16
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Chemie und Industrie
Pharmakologische Informationen
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
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.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Verwendung und Herstellung
General Manufacturing InformationPregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11.beta.)-: ACTIVE
Anwendungen
BeschreibungAldosterone is a mineralocorticosteroid that takes part in the regulation of electrolytic balance in the organism. Aldosterone lowers excretion of sodium ions from the body, thus increasing their reabsorption and increasing secretion of potassium ions in renal tubules. Being a competitive antagonist of aldosterone, spironlactone blocks aldosterone receptors, thus increasing excretion of sodium, chloride, and corresponding equivalents of water with urine, thus retaining the amount of potassium ions in the organism. Spironolactone is used both individually as well as in combination with thiazides, since it lowers kaliuresis caused by thiazide diuretics.
Zugehörige Reaktionen
3
Notizen zur Verbindung
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