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49697-38-3

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49697-38-3 Usage

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.

Originator

Akzo (Netherlands)

Uses

Anti-inflammatory (local).

Brand name

Vexol (Alcon).

General Description

Rimexolone, 11β-hydroxy-16α,17α-dimethyl-17-(1-oxopropyl)androsta-1,4-diene-3-one,like medrysone and fluorometholone, lacks the C21 OHgroup. In addition, rimexolone has an additional methylgroup in the 17 -position, a site where an OH group is typicallyfound. Rimexolone is available as a suspension forophthalmic use.

Check Digit Verification of cas no

The CAS Registry Mumber 49697-38-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,9,6,9 and 7 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 49697-38:
(7*4)+(6*9)+(5*6)+(4*9)+(3*7)+(2*3)+(1*8)=183
183 % 10 = 3
So 49697-38-3 is a valid CAS Registry Number.
InChI:InChI=1/C23H32O4/c1-13-10-17-16-7-6-14-11-15(24)8-9-21(14,2)19(16)18(25)12-22(17,3)23(13,4)20(26)27-5/h8-9,11,13,16-19,25H,6-7,10,12H2,1-5H3/t13-,16+,17+,18+,19-,21+,22+,23-/m1/s1

49697-38-3 Well-known Company Product Price

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  • USP

  • (1604600)  Rimexolone  United States Pharmacopeia (USP) Reference Standard

  • 49697-38-3

  • 1604600-100MG

  • 4,662.45CNY

  • Detail

49697-38-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Rimexolone

1.2 Other means of identification

Product number -
Other names Asoprisnil ecamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:49697-38-3 SDS

49697-38-3Synthetic route

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

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

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
With hydrogenchloride In methanol at 0 - 20℃; for 2.5h; Hydrolysis;97%
prednisolon
50-24-8

prednisolon

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
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
View Scheme
11β,17α-dihydoxy-21-iodopregna-1,4-diene-3,10-dione
49757-06-4

11β,17α-dihydoxy-21-iodopregna-1,4-diene-3,10-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: NaI; HOAc / acetone / Heating
2.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C
3.1: 1.42 g / DMAP; pyridine / 25 h
4.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C
4.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C
5.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
6.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
7.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
11β,17-dihydroxy-21-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione
110558-70-8

11β,17-dihydroxy-21-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: NaI / acetone / 20 °C
2.1: NaI; HOAc / acetone / Heating
3.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C
4.1: 1.42 g / DMAP; pyridine / 25 h
5.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C
5.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C
6.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
7.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
8.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
11β,17α-dihydroxypregna-1,4-diene-3,20-dione
20423-99-8

11β,17α-dihydroxypregna-1,4-diene-3,20-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C
2.1: 1.42 g / DMAP; pyridine / 25 h
3.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C
3.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C
4.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
5.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
6.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
11β-hydroxy-1,4,16-trienepregna-3,20-dione
60124-50-7

11β-hydroxy-1,4,16-trienepregna-3,20-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1.42 g / DMAP; pyridine / 25 h
2.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C
2.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C
3.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
4.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
5.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione
60124-51-8

11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C
1.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C
2.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
3.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
4.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
21-methyl-11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione
207346-24-5

21-methyl-11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C
2: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
3: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme
16α,21-dimethyl-11β,20-bis(trimethylsiloxy)-pregna-1,4,17(20)-trien-3-one
226712-41-0

16α,21-dimethyl-11β,20-bis(trimethylsiloxy)-pregna-1,4,17(20)-trien-3-one

rimexolone
49697-38-3

rimexolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C
2: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C
View Scheme

49697-38-3Downstream Products

49697-38-3Relevant articles and documents

Synthesis of the 16α,17α,21-trimethyl corticosteroid rimexolone from prednisolone

Conrow, Raymond E.

, p. 1042 - 1044 (2007/10/03)

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