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N-(3',4'-dimethoxycinnamoyl)anthranilic acid

HCID 5527
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Basic information

CAS
53902-12-8
Standard SMILES
COc1ccc(C=CC(=O)Nc2ccccc2C(=O)O)cc1OC
InChIKey
NZHGWWWHIYHZNX-UHFFFAOYSA-N
Molecular formula
C18H17NO5
Average molar mass
327.3 g/mol
Monoisotopic mass
327.11067264

Names & identifiers

Preferred name
N-(3',4'-dimethoxycinnamoyl)anthranilic acid
IUPAC
2-[3-(3,4-dimethoxyphenyl)prop-2-enoylamino]benzoic acid
English name
Tranilast
Molecular formula
C18H17NO5
Molecular weight
327.33

Names & synonyms

N-(3',4'-dimethoxycinnamoyl)anthranilic acidDTXSID7023693RefChem:1091097DTXCID808101892-[3-(3,4-dimethoxyphenyl)prop-2-enoylamino]benzoic acidTranilast trans-MK 341;SB 252218Tranilast Impurity 30Spectrum2_000042Spectrum3_001961SCHEMBL29876SPBio_000163
Show more names
n-5’MK 341TraniLQunistrizabenTranproranilasQunisterSB-252218TRANILAST
orb1305160orb3025012SCHEMBL30053800KBio3_002905NZHGWWWHIYHZNX-UHFFFAOYSA-NBDBM788864HMS3267I14HMS3372C04

Database identifiers

CAS
53902-12-8
PubChem CID
5527
DTXSID
DTXSID7023693

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
84.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
24
Formal charge
0
Complexity
464

Physicochemical properties

Melting point
166.2 · 166.2-168.2 °C (lit.)
Boiling point
465.23 °C · 465.23°C (rough estimate)
Density
1.3185 · 1.3185 (rough estimate)
refractive index
1.51 · 1.5100 (estimate)
storage temp.
2 · 2-8°C
solubility
18 mg/mL · DMSO: 18 mg/mL
form
powder
pka
3.47 · 3.47±0.36(Predicted)
color
white to beige
Merck
14 · 14,9570
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
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
SMILES
COc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1OC
CAS DataBase Reference

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
DG8731000
hs_code
2924.29.6250
Toxicity
LD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385)
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501

Chemistry & industry

Applications · 4 items

DescriptionTranilast (53902-12-8) is an anti-allergy agent (inhibitor of mast cell degranulation) that has been shown to have potent immunomodulatory effects via inhibition of endotoxin induced: PGE2, IC50 = 1-20 μM; TXB2, IC50 = 10-50 μM; TGFβ1, IC50 = 100-200 μM; IL-8, IC50 = 100 μM .1-3 Tranilast also displays anti-angiogenic properties.4,5

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

Usescoronary vasodilator

UsesTranilast 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), 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. 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. 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.[Cayman Chemical]

Upstream & downstream products

Upstream raw materials

Anthranilic acidSodium hydroxideBenzenesulfonyl chloride4-Dimethoxycinnamic AcidMethyl anthranilate3,4-Dimethoxycinnamic acid

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Related reactions

14 records
New reaction record
HRID 1153881 reaction equation
HRID 1153881As productuspto-grants-1984_12
HRID 1153882 reaction equation
HRID 1153882As productuspto-grants-1984_12
HRID 1579043 reaction equation
HRID 1579043As productuspto-grants-1976_02
HRID 1588957 reaction equation
HRID 1588957As productuspto-grants-1993_06
HRID 1588958 reaction equation
HRID 1588958As productuspto-grants-1993_06
HRID 1588959 reaction equation
HRID 1588959As productuspto-grants-1993_06
HRID 1588960 reaction equation
HRID 1588960As productuspto-grants-1993_06
HRID 1588961 reaction equation
HRID 1588961As productuspto-grants-1993_06
Page 1 of 2

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
53902 · 53902-12-8(CAS DataBase Reference)
FDA UNII
50 SMY6E · HVF50SMY6E
UNSPSC Code
51111800 · 51111800
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
8731000 · DG8731000
HS Code
2924.29 · 2924.29.6250
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Toxicity
50 in · LD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385)

Additional notes

DefinitionChEBI: An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.