11beta-Hydroxyprogesterone
Catalog Number: BT-255730
CAS Number: 600-57-7
Molecular Formula: C₂₁H₃₀O₃
Molecular Weight: 330.5 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
11beta-Hydroxyprogesterone is a steroid hormone that is produced naturally in the adrenal gland and placenta. It is a precursor to cortisol and has been found to have potential therapeutic effects in various medical conditions. This paper aims to provide an overview of the synthesis, chemical structure, biological activity, and potential applications of 11beta-Hydroxyprogesterone.
Properties
CAS Number
600-57-7
Product Name
11beta-Hydroxyprogesterone
IUPAC Name
(8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Molecular Formula
C₂₁H₃₀O₃
Molecular Weight
330.5 g/mol
InChI
InChI=1S/C21H30O3/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/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1
InChI Key
BFZHCUBIASXHPK-ATWVFEABSA-N
SMILES
CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
Synonyms
11 alpha-hydroxyprogesterone
11 beta-hydroxy-4-pregnen-3,20-dione
11-hydroxyprogesterone
11-hydroxyprogesterone, (11alpha)-(+-)-isomer
11-hydroxyprogesterone, (11alpha)-isomer
11-hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomer
11-hydroxyprogesterone, (11beta)-isomer
11-hydroxyprogesterone, (9beta,10alpha,11alpha)-isomer
11beta-hydroxyprogesterone
11OHP compound
Duralutin
Gesterol
Hy-Gestrone
Hylutin
Hyprogest
Pergestron
pregn-4-ene-11 beta-ol-3,20-dione
Pro-Depo
Prodrox
11 beta-hydroxy-4-pregnen-3,20-dione
11-hydroxyprogesterone
11-hydroxyprogesterone, (11alpha)-(+-)-isomer
11-hydroxyprogesterone, (11alpha)-isomer
11-hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomer
11-hydroxyprogesterone, (11beta)-isomer
11-hydroxyprogesterone, (9beta,10alpha,11alpha)-isomer
11beta-hydroxyprogesterone
11OHP compound
Duralutin
Gesterol
Hy-Gestrone
Hylutin
Hyprogest
Pergestron
pregn-4-ene-11 beta-ol-3,20-dione
Pro-Depo
Prodrox
Canonical SMILES
CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
Isomeric SMILES
CC(=O)[C@H]1CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C
Method of Synthesis or Extraction
11beta-Hydroxyprogesterone can be synthesized from progesterone through a series of chemical reactions. The most commonly used method involves the oxidation of progesterone using Jones reagent, followed by reduction with sodium borohydride. The yield of this method is around 50%, and it requires the use of toxic and hazardous chemicals, making it environmentally unfriendly. Another method involves the use of enzymes to convert progesterone to 11beta-Hydroxyprogesterone, which is a more sustainable and environmentally friendly approach. However, this method is less efficient and has a lower yield.
Chemical Structure and Biological Activity
11beta-Hydroxyprogesterone has a chemical structure similar to that of cortisol, with a hydroxyl group at the 11th position. It acts as a glucocorticoid receptor agonist and has been found to have anti-inflammatory and immunosuppressive effects. It also has mineralocorticoid receptor agonist activity, which can lead to sodium and water retention. The potency of 11beta-Hydroxyprogesterone is lower than that of cortisol, but it has a longer half-life, making it a potential therapeutic agent.
Biological Effects
11beta-Hydroxyprogesterone has been found to have various biological effects on cell function and signal transduction. It can inhibit the production of pro-inflammatory cytokines and chemokines, reduce the activation of immune cells, and modulate the expression of genes involved in inflammation and immune response. It has also been shown to have potential therapeutic effects in conditions such as rheumatoid arthritis, asthma, and inflammatory bowel disease. However, it can also have potential toxic effects, such as increasing the risk of infections and impairing wound healing.
Applications
In medical research, 11beta-Hydroxyprogesterone has been studied for its potential role in drug development. It has been used in clinical trials for the treatment of various conditions, such as multiple sclerosis, systemic lupus erythematosus, and psoriasis. The benefits of 11beta-Hydroxyprogesterone include its anti-inflammatory and immunosuppressive effects, as well as its longer half-life compared to cortisol. However, potential side effects include sodium and water retention, increased risk of infections, and impaired wound healing.
In environmental research, 11beta-Hydroxyprogesterone has been studied for its effects on ecosystems and its potential role in pollution management. It has been found to have endocrine-disrupting effects on aquatic organisms, such as fish and amphibians. It can also affect the growth and development of plants. However, further research is needed to fully understand the environmental impact of 11beta-Hydroxyprogesterone.
In industrial research, 11beta-Hydroxyprogesterone has been used in manufacturing processes to improve product quality and efficiency. It has also been studied for its potential health and safety considerations in the workplace. However, further research is needed to fully understand the potential risks and benefits of using 11beta-Hydroxyprogesterone in industrial settings.
In environmental research, 11beta-Hydroxyprogesterone has been studied for its effects on ecosystems and its potential role in pollution management. It has been found to have endocrine-disrupting effects on aquatic organisms, such as fish and amphibians. It can also affect the growth and development of plants. However, further research is needed to fully understand the environmental impact of 11beta-Hydroxyprogesterone.
In industrial research, 11beta-Hydroxyprogesterone has been used in manufacturing processes to improve product quality and efficiency. It has also been studied for its potential health and safety considerations in the workplace. However, further research is needed to fully understand the potential risks and benefits of using 11beta-Hydroxyprogesterone in industrial settings.
Future Perspectives and Challenges
Current limitations in the use and study of 11beta-Hydroxyprogesterone include its low potency compared to cortisol and its potential toxic effects. Possible solutions and improvements include the development of more potent analogs and the use of targeted delivery systems to reduce potential side effects. Future trends and prospects in the application of 11beta-Hydroxyprogesterone in scientific research include its potential use in personalized medicine and its role in the development of new therapies for inflammatory and autoimmune diseases. However, further research is needed to fully understand the potential benefits and risks of using 11beta-Hydroxyprogesterone in various applications.
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