Rimexolona

Base Information

• Chemical Name: Rimexolona
• CAS No.: 49697-38-3
• Molecular Formula: C24H34O3
• Molecular Weight: 370.532
• Hs Code.: 2937290000
• ChEMBL ID: CHEMBL111461
• Mol file: 49697-38-3.mol

Synonyms:Rimexolone [USAN:BAN:INN];Rimexolonum [INN-Latin];Rimexolona [INN-Spanish];C24H34O3;AL 02178;Rimexolone [USAN:INN:BAN];11beta-Hydroxy-16alpha,17,21-trimethyl-1,4-pregnadien-3,20-dion;CHEMBL111461;SCHEMBL1651214;11-beta-hydroxy-16-alpha,17-alpha-dimethyl-17-propionylandrosta-1,4-dien-3-one;(11-beta,16-alpha,17-beta)-11-Hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one;(11beta,16alpha,17beta)-11-Hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one;Androsta-1,4-dien-3-one, 11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)-, (11beta,16alpha,17beta)-;LS-19341;11 beta-hydroxy-16 alpha,17 alpha,21-trimethylpregna-1,4-diene-3,20-dione;(11 beta,16 alpha,17 beta)-11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one;(2R,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-14-propanoyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

Chemical Property of Rimexolona

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 258-268oC
• Boiling Point: 507°Cat760mmHg
• PKA: 14.42±0.70(Predicted)
• Flash Point: 274.5°C
• PSA: 54.37000
• Density: 1.12
• LogP: 4.49650
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 370.25079494
• Heavy Atom Count: 27
• Complexity: 749

Purity/Quality:

Rimexolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C1(C(CC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)C)C
• Isomeric SMILES: CCC(=O)[C@]1([C@@H](CC2[C@@]1(C[C@@H](C3C2CCC4=CC(=O)C=C[C@]34C)O)C)C)C
• Description: Rimexolone, an ophthalmic corticosteroid, was launched in 1995 in the U.S.A. for the treatment of postoperative inflammation following ocular surgery and anterior uveitis. Rimexolone has high corticoid receptor affinity and is a potent local antiinflammatory agent with minimal systemic effects and virtually no atrophogenic action in many animal models studied, unique among a wide range of topical steroids. Rapid onset, long duration of action plus a superior safety profile are characteristics of rimexolone. It was also approved in Europe for the treatment of rheumatoid arthritis and is currently in clinical trials for tendinitis and osteoarthritis.
• Uses: Anti-inflammatory (local).

Technology Process of Rimexolona

There total 13 articles about Rimexolona 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: 97.0%

11β-(trimethylsiloxy)-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione (220983-31-3) → rimexolone (49697-38-3)

Guidance literature:

With hydrogenchloride; In methanol; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/jo981848x

Reference yield: 1.5%

11β-acetoxy-16α,17α-dimethyl-5β-pregnane-3,20-dione 3,3-dimethyl acetal (49848-61-5) + methyl iodide (74-88-4) → (8S,10R,13S,14S,16R,17S)-17-(2-Bromo-propionyl)-11-hydroxy-10,13,16,17-tetramethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (79409-33-9) + (8S,10R,13S,14S,16R,17S)-11-Hydroxy-17-(2-methoxy-propionyl)-10,13,16,17-tetramethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (79400-17-2) + (8S,10R,13S,14S,16R,17S)-4-Bromo-11-hydroxy-10,13,16,17-tetramethyl-17-propionyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (79400-15-0) + 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-diene-3,20-dione (49697-38-3,49698-25-1)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1039/P19810002306

Reference yield:

prednisolon (50-24-8,8056-11-9) → rimexolone (49697-38-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine / 5 °C

2.1: NaI / acetone / 20 °C

3.1: NaI; HOAc / acetone / Heating

4.1: 1.40 g / semicarbazide*HCl / H₂O; acetic acid / 9.7 h / 80 - 85 °C

5.1: 1.42 g / DMAP; pyridine / 25 h

6.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C

6.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C

7.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C

8.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

9.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C

With pyridine; hydrogenchloride; dmap; 4 A molecular sieve; semicarbazide hydrochloride; trimethyl(benzyl)ammonium fluoride; acetic acid; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetic acid; acetone; 1.1: Tosylation / 2.1: Substitution / 3.1: Dehalogenation / 4.1: Dehydration / 5.1: silylation / 6.1: Metallation / 6.2: Methylation / 7.1: Addition / 8.1: Methylation / 9.1: Hydrolysis;

DOI:10.1021/jo981848x

upstream raw materials:

11β-propionyloxy-16α,17α,21-trimethylpregna-1,4-diene-3,20-dione

11β-acetoxy-16α,17α-dimethyl-5β-pregnane-3,20-dione 3,3-dimethyl acetal

methyl iodide

11β-(trimethylsiloxy)-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione

Refernces

• 1、 Cairns, James,Logan, Robert T.,McGarry, George,Roy, Robert G.,Stevenson, Donald F. M.,Woods, Gilbert F.. "Alkylated Steroids. Part 3. The 21-Alkylation of 20-Oxopregnanes and Synthesis of a Novel Anti-inflammatory 16α,17α,21-Trimethyl Steroid (Org 6216)". . p. 2306 - 2316. Retrieved 2007/10/02.