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53902-12-8 molecular structure
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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 and InChIs

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

Cite this record

CBID:5256 http://www.chembase.cn/molecule-5256.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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)
CAS Number
53902-12-8
70806-55-2
MDL Number
MFCD00864787
PubChem SID
24278719
160968685
99444086
PubChem CID
5282230

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.5528402  H Acceptors
H Donor LogD (pH = 5.5) 1.6218046 
LogD (pH = 7.4) 0.20370603  Log P 3.5626285 
Molar Refractivity 91.5198 cm3 Polarizability 33.853416 Å3
Polar Surface Area 84.86 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.89  LOG S -4.59 
Solubility (Water) 8.40e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: >10 mg/mL expand Show data source
H2O: insoluble expand Show data source
Apperance
white to beige powder expand Show data source
Melting Point
166.2-168.2 °C(lit.) expand Show data source
Storage Condition
-20°C expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
DG8731000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
Safety Statements
26-36 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... VEGFA(7422), VEGFB(7423), VEGFC(7424) expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C18H17NO5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB07615 external link
Drug information: experimental
Selleck Chemicals - S1439 external link
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 external link
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 external link
Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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