565-96-8

Basic information

• Product Name: 11α-Hydroxy-5α-pregnane-3,20-dione
• Synonyms: 11α-Hydroxyallopregnane-3,20-dione
• CAS NO: 565-96-8
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.47698
• Mol File: 565-96-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 193-195 °C
• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 251°C
• Appearance: /
• Density: 1.112g/cm³
• Vapor Pressure: 9.95E-11mmHg at 25°C
• Refractive Index: 1.532
• PKA: 14.66±0.70(Predicted)
• CAS DataBase Reference: 11α-Hydroxy-5α-pregnane-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 11α-Hydroxy-5α-pregnane-3,20-dione(565-96-8)
• EPA Substance Registry System: 11α-Hydroxy-5α-pregnane-3,20-dione(565-96-8)

Safety Data

• Hazardous Substances Data: 565-96-8(Hazardous Substances Data)

Usage

Description

11α-Hydroxy-5α-pregnane-3,20-dione is a steroidal compound derived from the transformation pathway of progesterone by the fungus Rhizopus nigricans. It is characterized by its unique molecular structure, featuring a hydroxyl group at the 11α position and a ketone group at both the 3 and 20 positions. 11α-Hydroxy-5α-pregnane-3,20-dione serves as a monoform intermediate and byproduct in the biosynthetic process, indicating its potential significance in the field of pharmaceuticals and biochemistry.

Uses

Used in Pharmaceutical Industry:
11α-Hydroxy-5α-pregnane-3,20-dione is used as an intermediate compound for the synthesis of various steroidal drugs. Its unique structure allows for further chemical modifications, making it a valuable building block in the development of new medications with potential applications in treating hormonal disorders, inflammation, and other conditions related to steroid hormone imbalances.
Used in Research and Development:
In the field of biochemistry and molecular biology, 11α-Hydroxy-5α-pregnane-3,20-dione serves as an important research tool. It can be utilized to study the metabolic pathways of progesterone and other steroid hormones, as well as to investigate the enzymatic activities of Rhizopus nigricans and related fungi. This knowledge can contribute to the understanding of steroid biosynthesis and may lead to the discovery of novel bioactive compounds with therapeutic potential.
Used in Drug Delivery Systems:
Similar to gallotannin, 11α-Hydroxy-5α-pregnane-3,20-dione can also be explored for its potential applications in drug delivery systems. Its steroidal nature may allow for the development of targeted drug delivery platforms, particularly for steroidal drugs, enhancing their bioavailability and therapeutic efficacy.

InChI:InChI=1/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13,15-19,24H,4-11H2,1-3H3/t13-,15-,16+,17-,18+,19+,20-,21+/m0/s1

Upstream product

• 80-75-1 11-alpha-hydroxyprogesterone 
• 102291-06-5 3,3,20,20-Bis--5α-pregn-9(11)-en 
• 15807-38-2 20,20-ethanediyldioxy-3α-hydroxy-5β-pregnan-11-one 
• 115267-39-5 20,20-ethanediyldioxy-5β-pregnane-3α,11α-diol 
• 1162-56-7 6-dehydroprogesterone 
• 600-52-2 3α,11α-dihydroxy-5β-pregnan-20-one 
• 128-23-4 pregnanedione 
• 21063-87-6 11α-hydroxypregna-4,6-diene-3,20-dione 
• 884878-03-9 11α-acetoxy-3β-hydroxy-5α-pregnan-20-one 
• 565-91-3 3β,11α-dihydroxy-5α-pregnan-20-one 
• 566-65-4 dihydroprogesterone 

Downstream Products

• 565-91-3 3β,11α-dihydroxy-5α-pregnan-20-one 
• 516-15-4 11-Ketoprogesterone 
• 600-52-2 3α,11α-dihydroxy-5β-pregnan-20-one 
• 2089-06-7 5α-pregnane-3,11,20-trione 
• 565-98-0 3α,20β-dihydroxy-5β-pregnan-11-one 
• 565-99-1 UC₁₀₁₇ 
• 23930-19-0 Alphaxalone 
• 38398-44-6 3α,11α-dihydroxy-5α-pregnan-20-one 
• 565-92-4 5β-pregnan-3α,11β-diol-20-one 
• 1408057-11-3 3,20-dioxo-5β-pregnan-11α-yl pentafluorobenzoate 
• 1408057-14-6 20-oxo-11α-(pentafluorobenzoyl)oxy-5β-pregnan-3α-yl sulfate pyridinium salt 
• 1408057-12-4 3α-hydroxy-20-oxo-5β-pregnan-11α-yl pentafluorobenzoate 
• 1256911-22-4 20-oxo-5β-pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate 
• 1357077-97-4 20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate 

Relevant articles and documents

NEUROACTIVE STEROIDS AND METHODS OF PREPARATION

Disclosed are neuroactive steroid anaesthetic agents, methods for their preparation and compositions comprising the same. The invention provides scaled up and/or GMP methods for preparing neuroactive steroids, such as alfaxalone, alfadolone and alfadolone acetate.

Allopregnanolone and pregnanolone analogues modified in the C ring: Synthesis and activity

(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α- pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA A receptor. Their biological activity was measured by in vitro test with [3H]flunitrazepam as radioligand in which allopregnanolone and its active analogues stimulated the binding to the GABAA receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor.

NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE

The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.