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Details

Stereochemistry ACHIRAL
Molecular Formula C18H17NO5
Molecular Weight 327.3313
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRANILAST

SMILES

COC1=CC=C(\C=C\C(=O)NC2=C(C=CC=C2)C(O)=O)C=C1OC

InChI

InChIKey=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+

HIDE SMILES / InChI
Molecular Formula C18H17NO5
Molecular Weight 327.3313
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22753703 http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2185

Tranilast is an antiallergic drug developed by Kissei Pharmaceuticals. It was approved in 1982 for use in Japan and South Korea for bronchial asthma. Indications for keloid and hypertrophic scar were added in 1993. It has been used for the treatment of allergic disorders such as asthma, allergic rhinitis and atopic dermatitis. Tranilast is used for the treatment of bronchial asthma, keloid and hypertrophic scar, and allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.

CNS Activity

CNS Active
3913
Curator's Comment: Oral administration of tranilast inhibited the growth of rat gliomas in vivo, suggesting tranilast can cross the blood–brain barrier, tranilast has been patented for treating Alzheimer's disease

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Vascular endothelial growth factor A
2
Target ID: P15691
Gene ID: 281572.0
Gene Symbol: VEGFA
Target Organism: Bos taurus (Bovine)
Inhibitor
8297
 22.0 µM [IC50]
Inhibitor
8297
 100.0 µM [IC50]
Human dermal microvascular endothelial cells proliferation
1
Target ID: Human dermal microvascular endothelial cells proliferation
Inhibitor
8297
 136.0 µM [IC50]
Inhibitor
8297
 0.1 mM [IC50]
Inhibitor
8297
 110.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
RIZABEN

Approved Use

RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar.

Launch Date

1981
Primary
Approved
8429
RIZABEN

Approved Use

RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar.

Launch Date

1981
Primary
Approved
8429
RIZABEN

Approved Use

RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar.

Launch Date

1992
PubMed

PubMed

TitleDatePubMed
Effects of the new antiallergic drug 11-oxo-11H-pyrido[2,1-b] quinazoline-2-carboxylic acid on immediate allergic reactions.
1986 Nov
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Omeprazole Inhibits Pancreatic Cancer Cell Invasion through a Nongenomic Aryl Hydrocarbon Receptor Pathway.
2015 May 18
Patents

Patents

JP2007526793A
16
JP2008019221A
3
JP2008247789A
1
JP2008526322A
35
JP2008526371A
35
JP2009525790A
101
JP2010265326A
1
JP5337693B2
1
JPH0217115A
2
JPH09278653A
1
JPS6191168A
1

Sample Use Guides

In Vivo Use Guide
In general, for dosage regimen: For adults, take 1 capsule (100 mg of the active ingredient) at a time, 3 times a day. The dosage should be adjusted according to the disease, age or symptoms.
Route of Administration: Oral
In Vitro Use Guide
Tranilast suppressed the production of PGD2 in a dose-dependent manner with an IC50 of 0.1 mM in rat peritoneal mast cells. The glutathione-dependent conversion of [14C]PGH2 to PGD2 by PGD synthetase (PGH-D isomerase, EC 5.3.99.2) was inhibited by Tranilast, with 50% inhibition achieved at 0.08 mM in broken cell preparations of rat peritoneal mast cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:58 GMT 2023
Record UNII
HVF50SMY6E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRANILAST
INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BENZOIC ACID, 2-((3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)AMINO)-
Common Name English
N-(3',4'-DIMETHOXYCINNAMOYL)ANTHRANILIC ACID
Common Name English
2-((3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)AMINO)BENZOIC ACID
Systematic Name English
MK-341
Code English
TRANILAST [JAN]
Common Name English
N-5'
Common Name English
N-(3,4-Dimethoxycinnamoyl)anthranilic acid
Systematic Name English
NSC-758970
Code English
TRANILAST [MI]
Common Name English
Tranilast [WHO-DD]
Common Name English
TRANILAST [MART.]
Common Name English
tranilast [INN]
Common Name English
RIZABEN
Brand Name English
TRANILAST [USAN]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/10/756
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
FDA ORPHAN DRUG 176803
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
NCI_THESAURUS C574
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
FDA ORPHAN DRUG 311810
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
Code System Code Type Description
RXCUI
57330
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY RxNorm
MESH
C012293
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
DRUG BANK
DB07615
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL415324
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
INN
5070
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
WIKIPEDIA
Tranilast
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
PUBCHEM
5282230
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID7023693
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
CHEBI
77572
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
NCI_THESAURUS
C152712
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
NSC
758970
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
IUPHAR
6326
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
CAS
53902-12-8
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
SMS_ID
100000077473
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
MERCK INDEX
m11001
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2714
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
USAN
W-116
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
EVMPD
SUB11215MIG
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
FDA UNII
HVF50SMY6E
Created by admin on Fri Dec 15 15:24:58 GMT 2023 , Edited by admin on Fri Dec 15 15:24:58 GMT 2023
PRIMARY
Related Record Type Details
Structure of TRANILAST
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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