Tranilast

Cayman Chemical Item Number 13044

N-(3',4'-Dimethyoxycinnamoyl) Anthranilic Acid; Tranpro; MK 341; Rizaben; SB 252218 (CAS 53902-12-8)

Tranilast (CAS 53902-12-8)

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Description

Tranilast is a compound that exhibits anti-inflammatory and immunomodulatory effects by inhibiting lipid mediator and cytokine release from inflammatory cells and interfering with PDGF- and TGF-β1-induced proliferation and migration of vascular medial smooth muscle cells. Tranilast suppresses production of prostaglandin D2 (IC50 = 0.1 mM)1, prostaglandin E2 (IC50 = ~1-20 µM), thromboxane B2 (IC50 = ~10-50 µM), TGF-β1 (IC50 = ~100-200 µM), and interleukin-8 (IC50 = ~100 µM) in in vitro models as well as attenuates of the proinflammatory activity of human monocytes.2 While originally marketed as an antiallergenic drug, the efficacy of tranilast in preventing restenosis after percutaneous coronary intervention has been tested in a large-scale clinical trial.3 Additionally, tranilast inhibits VEGF-induced angiogenetic activities (i.e., proliferation, migration and tube formation of vascular endothelial cells) with IC50 values of 22, 18 and 193 µM, which may prove therapeutic for various retinal diseases.4

1 Ikai, K., Ujihara, M., Fujii, K., et al. Inhibitory effect of tranilast on prostaglandin D synthetase. Biochem Pharmacol 38(16) 2673-2676 (1989).

2 Capper, E.A., Roshak, A.K., Bolognese, B.J., et al. Modulation of human monocyte activities by tranilast, SB 252218, a compund demonstrating efficacy in restenosis. J Pharmacol Exp Ther 295(3) 1061-1069 (2000).

3 Holmes, D.R., Savage, M., LaBlanche, J., et al. Results of prevention of restenosis with tranilast and its outcomes (PRESTO) trial. Circulation 106 1243-1250 (2002).

4 Koyama, S., Takagi, H., Otani, A., et al. Tranilast inhibits protein kinase C-dependent signalling pathway linked to angiogenic activities and gene expression of retinal microcapillary endothelial cells. Br J Pharmacol 127 537-545 (1999).

Synonyms
  • N-(3',4'-Dimethyoxycinnamoyl) Anthranilic Acid
  • Tranpro
  • MK 341
  • Rizaben
  • SB 252218
Formal Name 2-​[[3-​(3,​4-​dimethoxyphenyl)-​1-​oxo-​2-​propen-​1-​yl]amino]-​benzoic acid
CAS Number 53902-12-8
Molecular Formula C18H17NO5
Formula Weight 327.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(/C=C/C1=CC=C(OC)​C(OC)​=C1)​NC2=C(C(O)​=O)​C=CC=C2
InCHI Code
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​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
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NZHGWWWHIYHZNX-CSKARUKUSA-N

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Tranilast is available in the following screening library:

Size Price Quantity Subtotal
5 mg $15.00 $0.00
10 mg $29.00 $0.00
50 mg $120.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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