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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;CS-1961;IGURATIMOD;Iguratimod >iguratimod( R&D);IguratiMod (T 614);Iguratimod USP/EP/BP;Iguratimod (intermediates I4,I6);N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide
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.

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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

Jiangsu Simcere Pharmaceutical CO.,Ltd
Tel
025-85566666-7321 15195996671
Email
API@simcere.com
Country
China
ProdList
19
Advantage
58
Jiangxi ravel Biotechnology Co.,Ltd
Tel
13184580281
Fax
400-880-2824
Email
hj@ruiweier.cn
Country
China
ProdList
2107
Advantage
58
NanJing Vtrying Pharmatech Co.,Ltd
Tel
17314186806
Email
Vtrying_sale@163.com
Country
China
ProdList
77
Advantage
58
Hubei jian chu biological technology co., LTD
Tel
027-027-65528353 13554206703
Email
3279834739@qq.com
Country
China
ProdList
1055
Advantage
58
Beijing Jingzi Pharmaceutical Technology Co., Ltd.
Tel
15011485209
Email
17241816@qq.com
Country
China
ProdList
81
Advantage
58
Hubei Hongxin Ruiyu Fine Chemical Co., Ltd.
Tel
027-65526929 15102793023
Fax
027-65526669
Email
hbhxry@163.com
Country
China
ProdList
1356
Advantage
55
Allikang Pharmaceutical Co., LTD
Tel
0573-87390950 13806705416
Email
wzj@alicornpharma.com
Country
China
ProdList
73
Advantage
58
Bayee Biotech (Anqing) Co., Ltd.
Tel
0556-5032306 18917961636
Fax
+86-556-5032307
Email
wtx@bayeebio.com
Country
China
ProdList
253
Advantage
61
NANJING TOMMLAB PHARMATECH Co.,LTD
Tel
--
Fax
--
Email
litianang@caremo.com.cn
Country
China
ProdList
228
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2923
Advantage
55
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View Lastest Price from Iguratimod manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Iguratimod 123663-49-0
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-04-29
Shaanxi Dideu Medichem Co. Ltd
Product
Iguratimod 123663-49-0
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
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

123663-49-0, IguratimodRelated Search:


  • 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)
  • 123663-49-0
  • Pharmaceutical intermediate
  • Pharmaceuticals
  • API
  • 123663-49-0