IGURATIMOD

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14N2O6S
Molecular Weight	374.368
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)NC1=CC2=C(C=C1OC3=CC=CC=C3)C(=O)C(NC=O)=CO2

InChI

InChIKey=ANMATWQYLIFGOK-UHFFFAOYSA-N

InChI=1S/C17H14N2O6S/c1-26(22,23)19-13-8-15-12(17(21)14(9-24-15)18-10-20)7-16(13)25-11-5-3-2-4-6-11/h2-10,19H,1H3,(H,18,20)

HIDE SMILES / InChI

Molecular Formula	C17H14N2O6S
Molecular Weight	374.368
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/23032798
Curator's Comment: Description was created based on several sources, including http://www.eisai.jp/medical/products/di/EPI/CRM_T_EPI.pdf

Iguratimod, a methanesulfonanilide, is an anti-inflammatory drug for the treatment of rheumatoid arthritis that has been developed exclusively in Japan and China. It inhibits the production of immunoglobulins and various inflammatory cytokines (interleukin-1, -6 and -8 and TNF), and exerts anabolic effects on bone metabolism by stimulating osteoblastic differentiation and inhibiting osteoclastogenesis. On the molecular level, it inhibits the nuclear transcription factor NF-κB but not its inhibitor, IκBα. In addition to these immunomodulatory and other long-lasting effects, iguratimod inhibits cyclooxygenase-2, which provides a synergistic short-term action against pain and inflammation. Efficacy and tolerability are comparable to salazosulfapyridine, and probably also to methotrexate. Combination with methotrexate is synergistic in patients with insufficient response to methotrexate and does not significantly increase adverse events.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25757926	Inhibitor 8504	10.8 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7650864	Inhibitor 8504	0.02 µM [IC50]
Tumor necrosis factor 6 Target ID: P16599 Gene ID: 103694380\|\|\|24835 Gene Symbol: Tnf Target Organism: Rattus norvegicus (Rat) Sources: http://www.ncbi.nlm.nih.gov/pubmed/16848314	Inhibitor 8504	26.2 µM [IC50]
Interleukin-6 4 Target ID: CHEMBL1795129 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1289500	Inhibitor 8504	0.018 µM [IC50]
Interleukin-1 beta 22 Target ID: CHEMBL1909490 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1289500	Inhibitor 8504
Tumor necrosis factor ligand superfamily member 11 1 Target ID: CHEMBL2364162 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26273599	Inhibitor 8504
Interleukin 17A 8 Target ID: CHEMBL3390822 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26273599	Inhibitor 8504
Matrix metalloproteinase 3 13 Target ID: CHEMBL283 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26273599	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 320 Sources: http://www.eisai.jp/medical/products/di/EPI/CRM_T_EPI.pdf	Primary		Approved 8583	Careram Approved Use Rheumatoid arthritis Launch Date 2012

C_max

Value	Dose	Analyte	Population
1.24 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.13 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.59 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.88 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
20.93 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
34.89 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
56.81 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
31.88 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
8.55 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.31 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.3 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10.25 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29051989/	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	IGURATIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/	Other AEs: Nausea, Abdominal distention... Other AEs: Nausea (grade 1, 16.7%) Abdominal distention (grade 1, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/
25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30143001/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30143001/	Disc. AE: Drug-induced hepatitis... AEs leading to discontinuation/dose reduction: Drug-induced hepatitis (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/30143001/
25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34150809/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34150809/	Disc. AE: Gastrointestinal disorder... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (grade 1, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/34150809/

AEs

AE	Significance	Dose	Population
Nausea	grade 1, 16.7%	75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/
Abdominal distention	grade 1, 33.3%	75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29051989/
Drug-induced hepatitis	grade 3 Disc. AE	25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30143001/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30143001/
Gastrointestinal disorder	grade 1, 16.7% Disc. AE	25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34150809/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34150809/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 CYP2C91 1 CYP2C93 1 CYP2B6 926 CYP2E1 1060 CYP19A1 429	CYP2E1 729 CYP1A2 1197 CYP2B6 776 N-acetyltransferase 1 CYP2C19 1119 P-gp 2052	rCYP2E1 2 CYP2C6 2

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206972	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	no
CYP2C9*1 1	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes [IC50 10.8 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes [IC50 14.1 uM]
CYP2C9*3 1	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes [IC50 20.1 uM]
CYP2C6 2	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=25 Page: 25.0	yes
rCYP2E1 6	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=25 Page: 25.0	yes

Drug as victim

Target	Modality	Activity	Metabolite
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144206972	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes
CYP2B6 776	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	yes
CYP2C19 1119	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes
CYP2D6 1388	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	yes
CYP2E1 729	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2012/P201200067/480297000_22400AMX00731000_A100_1.pdf#page=41 Page: 41.0	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes
N-acetyltransferase 1	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25757926/	yes	M1 18

PubMed

Title	Date	PubMed
A novel anti-rheumatic drug, T-614, stimulates osteoblastic differentiation in vitro and bone morphogenetic protein-2-induced bone formation in vivo.	2002 Dec 20	12470665
T-614, a novel immunomodulator, attenuates joint inflammation and articular damage in collagen-induced arthritis.	2008	19019215

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage for oral use is 25 mg of iguratimod once daily after breakfast for 4 weeks or more, after which the dosage should be increased to one 25 mg tablet taken twice daily (after breakfast and after supper).

Route of Administration: Oral

In Vitro Use Guide

20 ug/mL of Iguratimod decreased RANKL expression and RANKL/OPG ratio in IL-6-induced synovial fibroblasts from rheumatoid arthritis.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:39 GMT 2025`
Record UNII	4IHY34Y2NV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IGURATIMOD [JAN]

Preferred Name

English

IGURATIMOD

Official Name

English

Iguratimod [WHO-DD]

Common Name

English

T-614

Code

English

iguratimod [INN]

Common Name

English

N-(7-((METHYLSULFONYL)AMINO)-4-OXO-6-PHENOXY-4H-1-BENZOPYRAN-3-YL)FORMAMIDE

Systematic Name

English

IGURATIMOD [MI]

Common Name

English

CARERAM

Brand Name

English

KOLBET

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308