TRANILAST

Possibly Marketed Outside US

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 Search

SMILES

COC1=CC=C(\C=C\C(=O)NC2=CC=CC=C2C(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

Description
Sources: https://www.drugbank.ca/drugs/DB07615
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Vascular endothelial growth factor A 3 Target ID: P15691 Gene ID: 281572.0 Gene Symbol: VEGFA Target Organism: Bos taurus (Bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10385256	Inhibitor 8504	22.0 µM [IC50]
vascular smooth muscle cell proliferation 1 Target ID: GO:1990874 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10082476	Inhibitor 8504	100.0 µM [IC50]
Human dermal microvascular endothelial cells proliferation 1 Target ID: Human dermal microvascular endothelial cells proliferation Sources: https://www.ncbi.nlm.nih.gov/pubmed/9401770	Inhibitor 8504	136.0 µM [IC50]
Prostaglandin Synthesis and Regulation 6 Target ID: WP303 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2475113	Inhibitor 8504	0.1 mM [IC50]
leukotriene biosynthetic process 5 Target ID: GO:0019370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6194082	Inhibitor 8504	110.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bronchial asthma 50 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2185	Primary	Approved 8583	RIZABEN Approved Use RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar. Launch Date 1981
Allergic rhinitis 104 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2185	Primary	Approved 8583	RIZABEN Approved Use RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar. Launch Date 1981
Keloid 2 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2185	Primary	Approved 8583	RIZABEN Approved Use RIZABEN is used to treat bronchial asthma, allergic rhinitis, atopic dermatitis, keloid or hyperplastic scar. Launch Date 1992

C_max

Value	Dose	Analyte	Population
12.6 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_4490002C1123_1_002_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
22.2 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_4490002C1123_1_002_1F.pdf#page=23	2.5 mg/kg 3 times / day steady-state, oral dose: 2.5 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:	TRANILAST serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
17.8 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop single, ocular dose: 4 drop route of administration: Ocular experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
25 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop 4 times / day multiple, ocular dose: 4 drop route of administration: Ocular experiment type: MULTIPLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
10.04 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17044126/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
42.2 μg/mL EXPERIMENT https://www.jfda-online.com/journal/vol10/iss3/6/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
114.4 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_4490002C1123_1_002_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
50.8 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop single, ocular dose: 4 drop route of administration: Ocular experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
75.6 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop 4 times / day multiple, ocular dose: 4 drop route of administration: Ocular experiment type: MULTIPLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
93.02 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17044126/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
422 μg × h/mL EXPERIMENT https://www.jfda-online.com/journal/vol10/iss3/6/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
5.3 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_4490002C1123_1_002_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.6 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop single, ocular dose: 4 drop route of administration: Ocular experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.9 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_1319736Q1076_1_004_1F.pdf#page=17	4 drop 4 times / day multiple, ocular dose: 4 drop route of administration: Ocular experiment type: MULTIPLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17044126/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.58 h EXPERIMENT https://www.jfda-online.com/journal/vol10/iss3/6/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
18.3% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/230034_4490002C1123_1_002_1F.pdf#page=24			TRANILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
Omeprazole Inhibits Pancreatic Cancer Cell Invasion through a Nongenomic Aryl Hydrocarbon Receptor Pathway.	2015-05-18	25826687
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
Effects of the new antiallergic drug 11-oxo-11H-pyrido[2,1-b] quinazoline-2-carboxylic acid on immediate allergic reactions.	1986-11	2434109

Patents

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.

Name

Type

Language

TRANILAST

Official Name

English

RIZABEN

Preferred 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

TRANILAST [USAN]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/10/756