2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

• ChemBase ID: 5256
• Molecular Formular: C18H17NO5
• Molecular Mass: 327.33128
• Monoisotopic Mass: 327.11067265
• SMILES: c1(c(NC(=O)/C=C/c2cc(c(cc2)OC)OC)cccc1)C(=O)O
• Canonical SMILES: COc1cc(/C=C/C(=O)Nc2ccccc2C(=O)O)ccc1OC
• InChI: 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+
• InChIKey: NZHGWWWHIYHZNX-CSKARUKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid; 2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
• IUPAC Traditional name: tranilast
• Synonyms: 2-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid; 2-[3-(3,4-Dimethoxy-phenyl)-acryloylamino]-benzoic acid; 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino] benzoic acid; 3,4-DAA; N-(3,4-Dimethoxycinnamoyl)anthranilic acid; SB-252218; Tranilast; 2-[[(2E)-3-(3,4-Dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid; (E)-2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid; trans-Tranilast; Rizaben; SB 252218; MK 341; Tranpro; Tranilast(SB 252218)

Database IDs

• CAS Number: 53902-12-8; 70806-55-2
• MDL Number: MFCD00864787
• PubChem SID: 24278719; 99444086; 160968685
• PubChem CID: 5282230

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5528402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6218046
• LogD (pH = 7.4): 0.20370603
• Log P: 3.5626285
• Molar Refractivity: 91.5198 cm^3
• Polarizability: 33.853416 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.89
• LOG S: -4.59
• Solubility (Water): 8.40e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white to beige powder
• Melting Point: 166.2-168.2 °C(lit.)

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• RTECS: DG8731000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... VEGFA(7422), VEGFB(7423), VEGFC(7424)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H17NO5

DETAILS

DrugBank - DB07615

Drug information: experimental

Selleck Chemicals - S1439

Research Area: Rheumatoid arthritis, Hyp
Biological Activity:
Tranilast (Rizaben) is an antiallergic drug for bronchial asthma. It has been used for the treatment of allergic disorders such as asthma, allergic rhinitis and atopic dermatitis. It has also been investigated for use as an antiproliferative drug on drug-eluting stents. [1]

Sigma Aldrich - T0318

Biochem/physiol Actions
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.

Toronto Research Chemicals - T714565

Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

REFERENCES

• http://en.wikipedia.org/wiki/Tranilast
• Shiota, N., et al.: Brit. J. Pharmacol., 159, 626 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Kawabata, Y., et al.: Eur. J. Pharm. Sci., 39, 256 (2010)