Iguratimod

Product Name: Iguratimod
CAS No.: 123663-49-0
Chemical Name: Iguratimod
Synonyms: N-(7-(MethylsulfonaMido)-4-oxo-6-phenoxy-4H-chroMen-3-yl)forMaMide;T 614;ALM-3;CS-1961;IGURATIMOD;Iguratimod >iguratimod( R&D);IguratiMod (T 614);Iguratimod USP/EP/BP;Iguratimod, 10 mM in DMSO
CBNumber: CB91011295
Molecular Formula: C17H14N2O6S
Formula Weight: 374.37
MOL File: 123663-49-0.mol

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Iguratimod Property

Melting point:: 238.0 to 242.0 °C
Boiling point:: 580.6±60.0 °C(Predicted)
Density: 1.52±0.1 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: DMSO (Slightly)
form: Solid
pka: 5.58±0.20(Predicted)
color: White to Off-White

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Safety

HS Code: 2935.90.9500

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1898
Product name: Iguratimod
Purity: ≥98% (HPLC)
Packaging: 5MG
Price: $105
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML1898
Product name: Iguratimod
Purity: ≥98% (HPLC)
Packaging: 25MG
Price: $338
Updated: 2024/03/01

TCI Chemical

Product number: I0945
Product name: Iguratimod
Purity: >98.0%(HPLC)(T)
Packaging: 25mg
Price: $55
Updated: 2024/03/01

TCI Chemical

Product number: I0945
Product name: Iguratimod
Purity: >98.0%(HPLC)(T)
Packaging: 250mg
Price: $318
Updated: 2024/03/01

TRC

Product number: I265100
Product name: Iguratimod
Packaging: 50mg
Price: $95
Updated: 2021/12/16

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Iguratimod Chemical Properties,Usage,Production

Description

In August 2011, China’s State FDA approved Simcere Pharmaceutical Group’s new drug application for iguratimod (T-614), a disease modifying anti-rheumatic drug (DMARD) for the treatment of rheumatoid arthritis (RA). Preclinical in vivo studies indicated that iguratimod was effective in an established adjuvant-induced arthritis model (ED40=3.6 mg/kg) in rats and also efficacious in a type II collagen-induced arthritis model in DBA/1J mice at 30 mg and 100 mg/kg.

Originator

Toyama (Japan)

Uses

Iguratimod acts as an anti-inflammatory agent, used primarily in the treatment of rheumatoid arthritis.

Definition

ChEBI: Iguratimod is an organic molecular entity.

brand name

Iremod

Clinical Use

Iguratimod, which was discovered by Toyama Pharmaceuticals and jointly co-developed with Eisai in Japan, was approved by the PMDA (Pharmaceuticals and Medical Devices Agency) of Japan on June 29, 2012 for the treatment of rheumatoid arthritis. This drug was also independently developed by Simcere Pharmaceutical Group and is marked as Iremod® in China. The drug exhibited inhibitory effects on granuloma inflammation, and was shown to be efficacious for the prevention of joint destruction in adjuvant arthritis.

Synthesis

Several synthesis of iguratimod have been published, the most likely scale synthesis, which does not require chromatographic purification, is described in the scheme.The synthesis began with commercially available 3-nitro-4-chloro anisole (78) which was reacted with potassium phenoxide (generated from phenol and potassium t-butoxide at 110 oC) to provide the corresponding nitrophenyl ether which was subsequently reduced and sulfonylated to furnish sulfonamide 79. Next, this diphenyl ether was subjected to a Friedel-Crafts reaction with aminoacetonitrile hydrochloride which gave rise to aminomethylacetophenone 80 in 90% yield. This aminoketone was then formylated with formic trimethylacetic anhydride 81 at room temperature to afford formamide 82 in 91% yield, and this material was immediately subjected to O-demethylation conditions with aluminum trichloride and sodium iodide in acetonitrile to give the phenol 83 in 95% yield. Finally, treatment of the aminomethyl acetophenone phenol 83 with N,N-dimethylformamide dimethylacetal in DMF at low temperatures furnished iguratimod (XII) in 87% yield.

in vitro

iguratimod inhibited the release of immunoreactive il-1 beta from human monocytic cell line stimulated with lipopolysaccharides (lps) in a dose-dependent manner (0.3-30 μg/ml). northern blotting analysis using lps-stimulated thp-1 cells indicated that the inhibitory effect of iguratimod on il-1 beta production is caused by the suppression of il-1 beta mrna expression [1].

in vivo

administration of iguratimod did not inhibit the tumor growth, but resulted in attenuation of cachexia symptoms. furthermore, iguratimod decreased the serum levels of il-6, and also reduced its gene expression in the tumor tissues. in addition, exogenously administered il-6 nullified the suppressive effect of iguratimod [2].

target

COX-2

IC 50

2.0 (hepatocyte-stimulating activities) and 6.6 μg/ml (immunoreactivities) for il-6 release.

References

[1] tanaka k, aikawa y, kawasaki h, asaoka k, inaba t, yoshida c. pharmacological studies on 3-formylamino-7-methylsulfonylamino-6-phenoxy-4h-1-benzopyran-4-one (t-614), a novel antiinflammatory agent. 4th communication: inhibitory effect on the production of interleukin-1 and interleukin-6. j pharmacobiodyn. 1992;15(11):649-55.
[2] tanaka k, urata n, mikami m, ogasawara m, matsunaga t, terashima n, suzuki h. effect of iguratimod and other anti-rheumatic drugs on adenocarcinoma colon 26-induced cachexia in mice. inflamm res. 2007;56(1):17-23.
[3] hara m, abe t, sugawara s, mizushima y, hoshi k, irimajiri s, hashimoto h, yoshino s, matsui n, nobunaga m. long-term safety study of iguratimod in patients with rheumatoid arthritis. mod rheumatol. 2007;17(1):10-6.

Iguratimod Preparation Products And Raw materials

Raw materials

Preparation Products

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Iguratimod Suppliers

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View Lastest Price from Iguratimod manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Iguratimod 123663-49-0
Price: US $0.00/KG
Min. Order: 10g
Purity: 99%min
Supply Ability: 10kg
Release date: 2021-11-18

Hebei Junhua Import and Export Co., LTD

Product: Iguratimod 123663-49-0
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000
Release date: 2025-03-06

Hebei Chuanghai Biotechnology Co., Ltd

Product: Iguratimod 123663-49-0
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-20

123663-49-0, IguratimodRelated Search:

Dimethoxymethane 4-Chloro-3-nitroanisole Tapinarof Ambroxol Leflunomide Tacrolimus Methotrexate N,N-Dimethylformamide DIETHOXYMETHANE Chlorantraniliprole Formamide phenoxybenzamine 1-(3-phenoxyphenyl)ethanone Ethanone, 1-(4-amino-3-hydroxyphenyl)- (9CI) N-(4-ACETYL-PHENYL)-METHANESULFON-AMIDE 1-(4-AMINO-3-METHOXYPHENYL)-1-ETHANONE (2-PHENOXY)METHYLSULFONYLANILINE Iguratimod

IGURATIMOD

iguratimod( R&D)

T 614

N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide

3-(Formylamino)-7-(methylsulfonylamino)-6-phenoxy-4H-1-benzopyran-4-one

N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide

IguratiMod (T 614)

N-(7-(MethylsulfonaMido)-4-oxo-6-phenoxy-4H-chroMen-3-yl)forMaMide

CS-1961

N-[7-(methanesulfonamido)-4-oxo-6-phenoxy-1-benzopyran-3-yl]formamide

Iguratimod &gt

Methanesulfonamide, N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-

N-(3-Formamido-4-oxo-6-phenoxy-4H-chromen-7-yl)methanesulfonamide

N-[7-(Methanesulfonamido)-4-oxo-6-phenoxy-4H-chromen-3-yl]formamide

Iguratimod USP/EP/BP

IguratimodQ: What is Iguratimod Q: What is the CAS Number of Iguratimod Q: What is the storage condition of Iguratimod Q: What are the applications of Iguratimod

Iguratimod (intermediates I4,I6)

N-(7-(Methylsulfonamido)-4-oxo-6-phenoxy-4H-chromen-3-yl)formamide (Iguratimod Impurity)

3-Formylamino-7-methylsulfonamido-6-phenoxy-4h-1-benzopyran-4-one

ALM-3

Iguratimod, 10 mM in DMSO

123663-49-0

Pharmaceutical intermediate

Pharmaceuticals

API

123663-49-0

1