(10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

Base Information

• Chemical Name: (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
• CAS No.: 53-03-2
• Molecular Formula: C21H26O5
• Molecular Weight: 358.434
• Hs Code.: 2937210000
• NSC Number: 757289
• Mol file: 53-03-2.mol

Synonyms:(10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;Spectrum_000828;Spectrum2_001292;Spectrum3_000756;Spectrum4_000971;Spectrum5_000988;BSPBio_002372;KBioGR_001341;KBioSS_001308;DivK1c_000666;SPECTRUM1500499;SPBio_001323;SCHEMBL13043964;HMS502B08;KBio1_000666;KBio2_001308;KBio2_003876;KBio2_006444;KBio3_001592;NINDS_000666;HMS1920J16;HMS2092A17;HMS3373K22;Pharmakon1600-01500499;CCG-39230;NSC757289;NSC-757289;IDI1_000666;SMP2_000307;NCGC00178682-01;SBI-0051490.P003;AB00052078_02;A829356;AA-504/07226001;SR-05000002076;SR-05000002076-1;BRD-A62525898-001-02-9;BRD-A62525898-001-04-5;(10R,13S,17R)-10,13-dimethyl-17-oxidanyl-17-(2-oxidanylethanoyl)-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;(10R,13S,17R)-17-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;17-glycoloyl-17-hydroxy-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione

Chemical Property of (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.51E-15mmHg at 25°C
• Melting Point: 236-238 °C(lit.)
• Refractive Index: 170 ° (C=0.5, Dioxane)
• Boiling Point: 573.7 °C at 760 mmHg
• PKA: 12.36±0.60(Predicted)
• Flash Point: 314.8 °C
• PSA: 91.67000
• Density: 1.3 g/cm³
• LogP: 1.76580
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride. It shows polymorphism (5.9).
• Water Solubility.: 115mg/L(25 oC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 358.17802393
• Heavy Atom Count: 26
• Complexity: 764

Purity/Quality:

99% ^*data from raw suppliers

Prednisone-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,F
• Hazard Codes: Xn,C,F
• Statements: 63-34-11
• Safety Statements: 36/37/39-45-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CC(=O)C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C
• Isomeric SMILES: C[C@]12CC(=O)C3C(C1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@]34C
• Uses: Adrenocortical steroid. Glucocorticoid, antiinflammatory. Downregulates TNF-α production and NF-κB expression Prednisone is used for the same indications as cortisone for inflammatory processes, allergies, and adrenal gland insufficiency; however, it is somewhat more active than cortisone and has less of an effect on mineral volume.
• Indications: Prednisone 2.5 to 7.5 mg, administered at night or dexamethasone 0.25 to 0.75 mg are useful in female patients, with severe acne unresponsive to conventional therapy, who suffer from adrenal gland overproduction of androgens such as congenital adrenal hyperplasia.

Technology Process of (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

There total 15 articles about (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Cortisone (53-06-5) → Prednison (53-03-2)

Guidance literature:

With Rhodococcus coprophilus DSM 43347; In dimethyl sulfoxide; at 30 ℃; for 24h; Reagent/catalyst; regiospecific reaction; Green chemistry;

DOI:10.3390/molecules25092192

Reference yield: 89.0%

prednisone acetate (125-10-0) → Prednison (53-03-2)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; for 4h; Heating;

DOI:10.1016/j.steroids.2006.10.004

Reference yield: 30.0%

Cortisone (53-06-5) → Prednison (53-03-2) + 17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione (600-92-0)

Guidance literature:

With Rhodococcus rhodnii DSM 43960; In dimethyl sulfoxide; for 24h; Green chemistry; Enzymatic reaction;

DOI:10.3390/molecules26051352

upstream raw materials:

Cortisone

prednisone acetate

prednisolon

Prednisone pivalate

Downstream raw materials:

17α,20α,21-Trihydroxy-pregna-1,4-dien-3,11-dion

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione

Prednisone pivalate

17-hydroxy-21-phenoxyacetoxy-pregna-1,4-diene-3,11,20-trione

Refernces

Switch off/switch on regulation of drug cytotoxicity by conjugation to a cell targeting peptide

10.1016/j.ejmech.2014.07.073

This research aimed to develop a "switch off/switch on" regulation of drug cytotoxicity for targeted cancer therapy by conjugating anticancer drugs to bi-nuclear amino acid platforms (MAAPs) through solid-phase organic synthesis (SPOS). The purpose was to enhance the therapeutic efficacy of multiple drugs linked to a single carrier molecule, potentially improving target cell specificity and reducing side effects. The researchers synthesized MAAPs loaded with various anticancer agents, including Azatoxin (AZA), Camptothecin (CAMP), Prednisone (PRED), Chlorambucil (CLB), and the 9-aminoacridine anticancer compound YG-42. They demonstrated that the cytotoxic activity of these drugs could be controlled by chemical modification and delivery, effectively "switching off" the activity when conjugated to the MAAP and "switching on" when delivered to target cancer cells via a cell-targeting peptide. The conclusions supported the versatility of this approach for constructing MAAPs with various drugs and linkages, showing high variability in bio-stability and drug release kinetics. This research paves the way for more sophisticated MAAPs bearing diverse chemotherapeutic "cocktails" for preclinical cancer therapy assessment.