567-02-2

Basic information

• Product Name: 21-HYDROXYALLOPREGNANOLONE
• Synonyms: ALLOPREGNANE-3ALPHA,21-DIOL-20-ONE;ALLOTETRADEOXYCORTICOSTERONE;ALLOTETRAHYDROCORTEXONE;ALLOTETRAHYDRODEOXYCORTICOSTERONE;ALLOTETRAHYDRODESOXYCORTICOSTERONE;ALLOTETRAHYDRO DOC;ALLOTETRAHYDRO SUBSTANCE 'Q';ALLO TH DOC
• CAS NO: 567-02-2
• Molecular Formula: C₂₁H₃₄O₃
• Molecular Weight: 334.49
• EINECS: 209-300-8
• Mol File: 567-02-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 470.3 °C at 760 mmHg
• Flash Point: 252.3 °C
• Appearance: /
• Density: 1.115g/cm³
• Vapor Pressure: 8.07E-11mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 21-HYDROXYALLOPREGNANOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 21-HYDROXYALLOPREGNANOLONE(567-02-2)
• EPA Substance Registry System: 21-HYDROXYALLOPREGNANOLONE(567-02-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 567-02-2(Hazardous Substances Data)

Usage

Uses

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) has been used:as an γ-aminobutyric acid type A receptor (γ-GABAA) agonist in voltage-clamp measurements studies in Xenopus oocytesto test its effect on the spike-wave discharges (SWD) finasteride-treated ratsin electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury

General Description

3α21-Dihydroxy-5α-pregnan-20-one (THDOC) is a neurosteroid. It is synthesized in a two-step process from deoxycorticosterone (DOC) via 5α-dihydrodeoxycorticosterone (DHDOC) intermediate with enzymes 5α-reductase and 3α-hydroxysteroid oxidoreductase catalyzing these steps respectively.

Biochem/physiol Actions

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) is a positive allosteric modulator of the γ-aminobutyric acid A receptor (GABAA). By modulating GABAA receptor, THDOC allows sustained hyperpolarization and an increase in chloride influx and membrane conductance in neurons. THDOC, thus modulates neuronal excitability. It possesses anxiolytic, anticonvulsant and sedative properties. The levels of THDOC show variation in different physiological states. A low THDOC level in the mensural phase is speculated to play a role in the pathogenesis of catamenial epilepsy (CE) in women. However, elevated levels are reported in depression. THDOC may have an indirect role in the hypothalamic-pituitary–adrenal (HPA) axis activation during acute stress.

InChI:InChI=1/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3

Upstream product

• 911451-83-7 21,21-bis-benzyloxy-3β-hydroxy-pregn-5-en-20-one 
• 56-47-3 deoxycorticosterone acetate 
• 64-17-5 ethanol 
• 145-13-1 Pregnenolone 
• 516-55-2 isopregnanolone 
• 51296-50-5 (3β,5α)-21-bromo-3-hydroxypregnan-20-one 
• 298-36-2 5α-pregnan-21-ol-3,20-dione 
• 566-78-9 21-acetoxypregnenolone 
• 2402-24-6 (3β,5α)-21-(acetyloxy)-3-hydroxypregnan-20-one 
• 96611-83-5 3β-hydroxy-20-oxo-5α-pregnan-21-yl acetate 
• 225518-93-4 2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone 
• 516-54-1 tetrahydroprogesterone 
• 566-65-4 dihydroprogesterone 
• 225518-89-8 (3R,5S,8R,9S,10S,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene 

Relevant articles and documents

Suppressing aggressive behavior with analogs of allopregnanolone (epalon)

3α-Hydroxy-20-oxo-5α-pregnan-21-yl hemisuccinate (8) was produced by partial acylation of 3α,21-dihydroxy-5α-pregnan-20-one (14). 3α-Fluoro-5α-pregnan-20-one (9) was prepared by treatment of 3β-hydroxy-5α-pregnan-20-one (11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluoride. A behavioral test on mice was performed using 3α-hydroxy-5α-pregnan-20-one (1) and compounds 8 and 9. Compound 8 was found to be inactive, while the fluoro derivative 9 selectively reduced aggressive behavior in mice more than the corresponding 3α-hydroxy compound 1; locomotion and other behavioral features were not affected. Copyright

INHIBITORS OF GLUCOSE-6-PHOSPHATE DEHYDROGENASE FOR TREATING CARDIOVASCULAR AND PULMONARY CONDITIONS

The present disclosure provides for methods of treating or preventing a cardiovascular disorder and/or a related pulmonary disorder in a subject. In certain embodiments, the method comprises administering a therapeutically effective amount of an inhibitor of Glucose-6-phosphate dehydrogenase (G6PD), or a pharmaceutically acceptable salt, non-salt amorphous form, solvate, poly-morph, tautomer or prodrug thereof.

Novel steroid inhibitors of glucose 6-phosphate dehydrogenase

Novel derivatives of the steroid DHEA 1, a known uncompetitive inhibitor of G6PD, were designed, synthesized, and tested for their ability to inhibit this dehydrogenase enzyme. Several compounds with approximately 10-fold improved potency in an enzyme assay were identified, and this improved activity translated to efficacy in a cellular assay. The SAR for steroid inhibition of G6PD has been substantially developed; the 3β-alcohol can be replaced with 3β-H-bond donors such as sulfamide, sulfonamide, urea, and carbamate. Improved potency was achieved by replacing the androstane nucleus with a pregnane nucleus, provided a ketone at C-20 is present. For pregnan-20-ones incorporation of a 21-hydroxyl group is often beneficial. The novel compounds generally have good physicochemical properties and satisfactory in vitro DMPK parameters. These derivatives may be useful for examining the role of G6PD inhibition in cells and will assist the future design of more potent steroid inhibitors with potential therapeutic utility.