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49697-38-3

Rimexolone (100 MG), also known as 11β-hydroxy-16α,17α-dimethyl-17-(1-oxopropyl)androsta-1,4-diene-3-one, is an ophthalmic corticosteroid that was launched in 1995 in the U.S.A. It is similar to medrysone and fluorometholone, but lacks the C21 OH group and has an additional methyl group in the 17-position. Rimexolone is available as a suspension for ophthalmic use and is known for its high corticoid receptor affinity, potent local anti-inflammatory action, minimal systemic effects, and virtually no atrophogenic action in many animal models studied. It is unique among a wide range of topical steroids and is characterized by rapid onset, long duration of action, and a superior safety profile.

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  • 49697-38-3 Structure

  • Basic information

    1. Product Name: RIMEXOLONE (100 MG)
    2. Synonyms: RIMEXOLONE (100 MG);Rimexolone;(17S)-11β-Hydroxy-16α,17α-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one;11β-Hydroxy-16α,17α-dimethyl-17β-propionylandrosta-1,4-dien-3-one;Org-6216;(11b,16a,17b)-11-Hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one;(11β,16α,17β)-;(11β, 16α, 17β)-11-Hydroxy-16,17-dimethyl-17-(1-oxopropyl)androstra-1,4-dien-3-one
    3. CAS NO:49697-38-3
    4. Molecular Formula: C24H34O3
    5. Molecular Weight: 370.53
    6. EINECS: N/A
    7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
    8. Mol File: 49697-38-3.mol
    9. Article Data: 2

  • Chemical Properties

    1. Melting Point: 258-268 ºC
    2. Boiling Point: 507°Cat760mmHg
    3. Flash Point: 274.5°C
    4. Appearance: /
    5. Density: 1.12
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.561
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.42±0.70(Predicted)
    11. CAS DataBase Reference: RIMEXOLONE (100 MG)(CAS DataBase Reference)
    12. NIST Chemistry Reference: RIMEXOLONE (100 MG)(49697-38-3)
    13. EPA Substance Registry System: RIMEXOLONE (100 MG)(49697-38-3)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 49697-38-3(Hazardous Substances Data)

49697-38-3 Usage

Uses

Used in Ophthalmology:
Rimexolone (100 MG) is used as an anti-inflammatory agent for the treatment of postoperative inflammation following ocular surgery and anterior uveitis. It modulates the immune response and reduces inflammation in the eye, providing relief from symptoms and promoting healing.
Used in Rheumatology:
Rimexolone (100 MG) is used as an anti-inflammatory agent for the treatment of rheumatoid arthritis. It was approved in Europe for this application and helps to reduce inflammation and alleviate pain associated with the condition.
Used in Clinical Trials:
Rimexolone (100 MG) is currently being investigated in clinical trials for its potential use in treating tendinitis and osteoarthritis. Its anti-inflammatory properties make it a promising candidate for these applications.
Brand Name:
Rimexolone (100 MG) is marketed under the brand name Vexol (Alcon).

Originator

Akzo (Netherlands)

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

Alkylated Steroids. Part 3. The 21-Alkylation of 20-Oxopregnanes and Synthesis of a Novel Anti-inflammatory 16α,17α,21-Trimethyl Steroid (Org 6216)

Cairns, James,Logan, Robert T.,McGarry, George,Roy, Robert G.,Stevenson, Donald F. M.,Woods, Gilbert F.

, p. 2306 - 2316 (2007/10/02)

The development of a 21-alkylation reaction which proceeds via the lithium 20(21)-enolate is described and ats scope demonstrated by the preparation of a variety of 21-alkylpregnane derivatives.Application of this process to 11β-acetoxy-16α,17α-dimethyl-5α-pregnane-3,20-dione (28a) and its 5β-analogue (28b) led to the corresponding 16α,17α,21-trimethyl derivatives.Several routes from these saturated trimethylpregnane-3,20-diones to 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-diene-3,20-dione (Org 6216) were explored.The best method gave Org 6216 in 75percent yield.

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