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Merck

T0318

Sigma-Aldrich

Tranilast

≥98% (HPLC), powder

Sinónimos:

2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino] benzoic acid, 3,4-DAA, N-(3,4-Dimethoxycinnamoyl)anthranilic acid, Rizaben, SB-252218

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About This Item

Fórmula empírica (notación de Hill):
C18H17NO5
Número de CAS:
Peso molecular:
327.33
MDL number:
UNSPSC Code:
41106500
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

mp

166.2-168.2 °C (lit.)

solubility

DMSO: >10 mg/mL
H2O: insoluble

originator

Kissei

storage temp.

2-8°C

SMILES string

COc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1OC

InChI

1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+

InChI key

NZHGWWWHIYHZNX-CSKARUKUSA-N

Gene Information

Application

The effect of Tranilast on mast cell surface receptors was studied in murine bone marrow-derived mast cells.

Biochem/physiol Actions

Tranilast also inhibits vascular smooth muscle cell proliferation by inhibiting the cyclin-dependent kinase inhibitor-1(p21Waf1/Cip1) and may be useful in treating cardiac allograft vasculopathy. It is used in treating hypertrophic scars and keloids. Tranilast inhibits tumor necrosis factor (TNF-α and TGF-β2), obstructing epithelial-mesenchymal transition in human retinal pigment epithelial cell line (ARPE).
Tranilast is an anti-asthma drug, which inhibits LTC4 and PGE2 formation in stimulated monocytes, but does not inhibit cyclooxygenase or lipoxygenase activity; inhibits mast cell degranulation; inhibits VEGF-induced angiogenesis in vivo and also inhibits proliferation and tube formation of human endothelial cells in vitro. Tranilast may represent a new class of drugs for therapy to treat ongoing TH1-mediated autoimmune diseases.

Features and Benefits

This compound was developed by Kissei. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Philippe Lachapelle et al.
Pharmacology & therapeutics, 187, 98-113 (2018-02-21)
The transforming growth factor (TGF)-β cytokines play a central role in development and progression of chronic respiratory diseases. TGF-β overexpression in chronic inflammation, remodeling, fibrotic process and susceptibility to viral infection is established in the most prevalent chronic respiratory diseases
Tranilast inhibits cardiac allograft vasculopathy in association with p21waf1/cip1 expression on neointimal cells in murine cardiac transplantation model
Izawa A, et al.
Arteriosclerosis, Thrombosis, and Vascular Biology, 21(7), 1172-1178 (2001)
Tranilast inhibits the expression of genes related to epithelial-mesenchymal transition and angiogenesis in neurofibromin-deficient cells
Harigai R, et al.
Scientific reports, 8(1), 6069-6069 (2018)
Noriaki Minami et al.
Cancer medicine, 6(11), 2635-2645 (2017-10-06)
Therapeutic options for malignant brain tumors are limited, with new drugs being continuously evaluated. Organotypic brain slice culture has been adopted for neuroscience studies as a system that preserves brain architecture, cellular function, and the vascular network. However, the suitability
Md Imran Khan et al.
PloS one, 14(5), e0216427-e0216427 (2019-05-10)
In this report, using NMR and molecular modeling, we have studied the structure of lysozyme-S100A6 complex and the influence of tranilast [N-(3, 4-dimethoxycinnamoyl) anthranilic acid], an antiallergic drug which binds to lysozyme, on lysozyme-S100A6 and S100A6-RAGE complex formation and, finally

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