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SML1898

Sigma-Aldrich

Iguratimod

≥98% (HPLC)

Synonym(s):

3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one, IGU, N-(7-(Methylsulfonamido)-4-oxo-6-phenoxy-4H-chromen-3-yl)formamide, N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide, T-614

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About This Item

Empirical Formula (Hill Notation):
C17H14N2O6S
CAS Number:
123663-49-0
Molecular Weight:
374.37
MDL number:
MFCD00882374
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=S(NC1=CC(OC=C(NC([H])=O)C2=O)=C2C=C1OC3=CC=CC=C3)(C)=O

InChI

1S/C17H14N2O6S/c1-26(22,23)19-13-8-15-12(17(21)14(9-24-15)18-10-20)7-16(13)25-11-5-3-2-4-6-11/h2-10,19H,1H3,(H,18,20)

InChI key

ANMATWQYLIFGOK-UHFFFAOYSA-N

Biochem/physiol Actions

Iguratimod (T-614) is an orally active anti-inflammatory compound that inhibits NF-kappaB (NF-KB) p65 subunit (RelA) phosphorylation and nuclear translocation (30 μg/mL against 10 ng/mL TNF-α; human synovial cells) without affecting IKBα degradation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Joshua Bloom et al.
The Journal of biological chemistry, 291(51), 26502-26514 (2016-10-30)
Macrophage migration inhibitory factor (MIF) is a pleiotropic cytokine that has been implicated in a broad range of inflammatory and oncologic diseases. MIF is unique among cytokines in terms of its release profile and inflammatory role, notably as an endogenous
Taro Sakamoto et al.
Anticancer research, 36(7), 3301-3306 (2016-06-30)
Angiogenesis is a known factor for the development of hepatocellular carcinoma (HCC). The aim of this study was to assess the property of iguratimod, that is an anti-inflammatory drug for rheumatoid arthritis, on anti-angiogenesis and anti-carcinogensis for HCC. In vitro
Keiichi Tanaka et al.
Expert review of clinical immunology, 11(5), 565-573 (2015-03-24)
Iguratimod (IGU), a small-molecule compound, was developed as a disease-modifying antirheumatic drug in Japan. The pharmacological studies showed that inhibition of the production of cytokines and immunoglobulins mainly contributes to its improvement effect on animal arthritis models. The first clinical

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