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Merck

T0318

Tranilast

≥98% (HPLC), LTC4 inhibitor, powder

Synonym(s):

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

Empirical Formula (Hill Notation):
C18H17NO5
CAS Number:
53902-12-8
Molecular Weight:
327.33
UNSPSC Code:
41106500
PubChem Substance ID:
24278719
NACRES:
NA.77
MDL number:
MFCD00864787

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Product Name

Tranilast, ≥98% (HPLC), powder

SMILES string

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

InChI key

NZHGWWWHIYHZNX-CSKARUKUSA-N

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+

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

Quality Level

100

Gene Information

human ... VEGFA(7422), VEGFB(7423), VEGFC(7424)

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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.
Tranilast is an anti-asthma drug, which inhibits LTC4 and PGE2 formation in stimulated monocytes, inhibits mast cell degranulation, and inhibits VEGF-induced angiogenesis in vivo and also inhibits proliferation and tube formation of human endothelial cells in vitro.

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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000506444
0000506444
0000477147
0000417342
0000417343

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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)
Md Soriful Islam et al.
The Journal of clinical endocrinology and metabolism, 99(5), E775-E785 (2014-03-13)
Uterine leiomyomas are highly prevalent benign tumors of premenopausal women and the most common indication for hysterectomy. However, the exact etiology of this tumor is not fully understood. The objective of the study was to evaluate the role of activin-A
Venkateswaran Subramaniam et al.
Experimental and molecular pathology, 90(1), 116-122 (2010-11-03)
In the treatment of breast cancer, although a wide of choice of drugs and treatment modalities are available, drug resistance or drug toxicity poses a considerable challenge. Tranilast is a well tolerated drug used in the treatment of allergic disorders.
Gabrielle Zuniga et al.
Alzheimer's & dementia : the journal of the Alzheimer's Association, 19(2), 405-420 (2022-04-14)
While brains of patients with Alzheimer's disease and related tauopathies have evidence of altered RNA processing, we lack a mechanistic understanding of how altered RNA processing arises in these disorders and if such changes are causally linked to neurodegeneration. Using
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