565-99-1

Basic information

• Product Name: Renanolone
• Synonyms: Renanolone;3B-Hydroxy-5B-pregnane-11,20-dione;11-Oxopregnanolone;5β-Alphaxalone;(3R,5R,8S,9S,10S,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one;(3R,5R,8S,9S,10S,13S,14S,17S)-17-ethanoyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one
• CAS NO: 565-99-1
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.481
• Mol File: 565-99-1.mol

Chemical Properties

• Boiling Point: 504 °C at 760 mmHg
• Flash Point: 272.7 °C
• Appearance: /
• Density: 1.212 g/cm³
• Refractive Index: 1.562
• CAS DataBase Reference: Renanolone(CAS DataBase Reference)
• NIST Chemistry Reference: Renanolone(565-99-1)
• EPA Substance Registry System: Renanolone(565-99-1)

Safety Data

• Hazardous Substances Data: 565-99-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Renanolone is used as a sedative, anesthetic, and anticonvulsant agent for its strong sedative, anesthetic, and anticonvulsant properties.
Renanolone is used as a positive allosteric modulator of GABAA receptors for enhancing the inhibitory effects of the neurotransmitter GABA in the central nervous system.
Renanolone is used as an anti-inflammatory and analgesic agent for its potent anti-inflammatory and analgesic effects.
Used in Neurological and Psychiatric Conditions Treatment:
Renanolone is used as a potential candidate for the treatment of various neurological and psychiatric conditions due to its sedative, anesthetic, anticonvulsant, anti-inflammatory, and analgesic properties.
However, its use is limited due to its adverse effects on respiratory and cardiovascular function, as well as its potential for abuse and dependence. Further research is needed to fully understand the therapeutic potential and safety profile of Renanolone.

InChI:InChI=1/C20H30O4/c1-11(21)15-5-6-16-14-4-3-12-9-13(22)7-8-20(12,24)18(14)17(23)10-19(15,16)2/h12-16,18,22,24H,3-10H2,1-2H3/t12-,13-,14+,15-,16+,18-,19-,20-/m1/s1

Upstream product

• 2089-06-7 5α-pregnane-3,11,20-trione 
• 5009-82-5 3β-acetoxy-5α,9β-pregnane-11,20-dione 
• 2265-09-0 3β-acetoxy-17-bromo-16β-fluoro-5α-pregnane-11,20-dione 
• 911653-74-2 3β-acetoxy-5α,9β-pregn-7-ene-11,20-dione 
• 115484-60-1 (20Ξ)-3β,21-diacetoxy-23,24-dinor-5α-chola-7,20-diene 
• 115485-77-3 3β,20β_F-diacetoxy-9,11α-epoxy-5α-pregnan-7-one 
• 38368-22-8 (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-11-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 1169-20-6 3β-acetoxy-5α-pregn-16-en-20-one 
• 120576-48-9 (25R)-3β,26-diacetoxy-5α-furost-20(22)-en-11-one 
• 55647-25-1 5α-pregnane-3β,11α,20β_F-triol 
• 2724-68-7 3β-acetoxy-5α-pregn-16-ene-11,20-dione 
• 113926-54-8 3β-acetoxy-9,11α-epoxy-5α-pregn-7-en-20-one 
• 1449-60-1 5-dihydroergosteryl acetate 
• 1053-19-6 3β-acetoxy-20β_F-hydroxy-5α,9β-pregnan-11-one 

Downstream Products

• 2089-06-7 5α-pregnane-3,11,20-trione 
• 570-39-8 (3β,5α)-3,17-dihydroxypregnane-11,20-dione 
• 20703-79-1 21-bromo-3β,17-dihydroxy-5α-pregnane-11,20-dione 
• 23930-29-2 5α-pregnan-3α,11β-diol-20-one 
• 10417-85-3 5β-pregnane-3α,11β,20β_F-triol 
• 565-92-4 5β-pregnan-3α,11β-diol-20-one 
• 565-98-0 3α,20β-dihydroxy-5β-pregnan-11-one 
• 739-27-5 3α-hydroxy-5β-androstane-11,17-dione 
• 1610-52-2 3α-acetoxy-5β-pregnane-11,20-dione 
• 23930-19-0 Alphaxalone 
• 989-80-0 3β-(toluene-4-sulfonyloxy)-5α-pregnane-11,20-dione 
• 167947-08-2 (3β,5α)-21-(acetyloxy)-3-{[(4-methylphenyl)sulfonyl]oxy}pregnane-11,20-dione 

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.