Synonym
N7methanesulfonamido4oxo6(phenoxy)chromen3ylformamide
IUPAC/Chemical Name
N-(7-(methylsulfonamido)-4-oxo-6-phenoxy-4H-chromen-3-yl)formamide
InChi Key
ANMATWQYLIFGOK-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=CNC1=COC2=C(C=C(OC3=CC=CC=C3)C(NS(=O)(C)=O)=C2)C1=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Iguratimod is an antirheumatic agent, acts as an inhibitor of COX-2, with an IC50 of 20 μM (7.7 μg/mL), but shows no effect on COX-1. Iguratimod also inhibits macrophage migration inhibitory factor (MIF) with an IC50 of 6.81 μM.
In vitro activity:
This study found that activation markers, including CD25 and CD69, decreased significantly on day 3 in the presence of IGU (iguratimod) (Figures 2C , D). Collectively, these results indicate that IGU inhibits RA-CD4+ T cells proliferation and activation.
Reference: Front Immunol. 2022 Jun 1;13:757616. https://pubmed.ncbi.nlm.nih.gov/35720293/
In vivo activity:
The results showed that the hydroxyproline content (Fig. 2K) and fibrosis score (Fig. 2L) were decreased after IGU (iguratimod) administration. In short, the above results demonstrate that IGU can alleviate BLM (bleomycin)-induced pulmonary inflammation and fibrosis in mice.
Reference: Biomed Pharmacother. 2022 Sep;153:113460. https://pubmed.ncbi.nlm.nih.gov/36076570/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
14.0 |
37.40 |
| DMSO |
33.1 |
88.44 |
| PBS (pH 7.2) |
0.3 |
0.67 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
374.37
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Bai Z, Lu Z, Liu R, Tang Y, Ye X, Jin M, Wang G, Li X. Iguratimod Restrains Circulating Follicular Helper T Cell Function by Inhibiting Glucose Metabolism via Hif1α-HK2 Axis in Rheumatoid Arthritis. Front Immunol. 2022 Jun 1;13:757616. doi: 10.3389/fimmu.2022.757616. PMID: 35720293; PMCID: PMC9199372.
2. Zhang M, Lei YS, Meng XW, Liu HY, Li LG, Zhang J, Zhang JX, Tao WH, Peng K, Lin J, Ji FH. Iguratimod Alleviates Myocardial Ischemia/Reperfusion Injury Through Inhibiting Inflammatory Response Induced by Cardiac Fibroblast Pyroptosis via COX2/NLRP3 Signaling Pathway. Front Cell Dev Biol. 2021 Oct 25;9:746317. doi: 10.3389/fcell.2021.746317. PMID: 34760889; PMCID: PMC8573346.
3. Liu W, Han X, Li Q, Sun L, Wang J. Iguratimod ameliorates bleomycin-induced pulmonary fibrosis by inhibiting the EMT process and NLRP3 inflammasome activation. Biomed Pharmacother. 2022 Sep;153:113460. doi: 10.1016/j.biopha.2022.113460. Epub 2022 Jul 25. PMID: 36076570.
4. Hang Z, Wei J, Zheng M, Gui Z, Chen H, Sun L, Fei S, Han Z, Tao J, Wang Z, Tan R, Gu M. Iguratimod Attenuates Macrophage Polarization and Antibody-Mediated Rejection After Renal Transplant by Regulating KLF4. Front Pharmacol. 2022 May 9;13:865363. doi: 10.3389/fphar.2022.865363. PMID: 35614941; PMCID: PMC9125033.
In vitro protocol:
1. Bai Z, Lu Z, Liu R, Tang Y, Ye X, Jin M, Wang G, Li X. Iguratimod Restrains Circulating Follicular Helper T Cell Function by Inhibiting Glucose Metabolism via Hif1α-HK2 Axis in Rheumatoid Arthritis. Front Immunol. 2022 Jun 1;13:757616. doi: 10.3389/fimmu.2022.757616. PMID: 35720293; PMCID: PMC9199372.
2. Zhang M, Lei YS, Meng XW, Liu HY, Li LG, Zhang J, Zhang JX, Tao WH, Peng K, Lin J, Ji FH. Iguratimod Alleviates Myocardial Ischemia/Reperfusion Injury Through Inhibiting Inflammatory Response Induced by Cardiac Fibroblast Pyroptosis via COX2/NLRP3 Signaling Pathway. Front Cell Dev Biol. 2021 Oct 25;9:746317. doi: 10.3389/fcell.2021.746317. PMID: 34760889; PMCID: PMC8573346.
In vivo protocol:
1. Liu W, Han X, Li Q, Sun L, Wang J. Iguratimod ameliorates bleomycin-induced pulmonary fibrosis by inhibiting the EMT process and NLRP3 inflammasome activation. Biomed Pharmacother. 2022 Sep;153:113460. doi: 10.1016/j.biopha.2022.113460. Epub 2022 Jul 25. PMID: 36076570.
2. Hang Z, Wei J, Zheng M, Gui Z, Chen H, Sun L, Fei S, Han Z, Tao J, Wang Z, Tan R, Gu M. Iguratimod Attenuates Macrophage Polarization and Antibody-Mediated Rejection After Renal Transplant by Regulating KLF4. Front Pharmacol. 2022 May 9;13:865363. doi: 10.3389/fphar.2022.865363. PMID: 35614941; PMCID: PMC9125033.
1: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Oct;30(8):643-72. PubMed PMID: 19088949.
2: Zhou T, Ding L, Li X, Zhang F, Zhang Q, Gong B, Guo X. Determination of iguratimod in rat plasma by high performance liquid chromatography: method and application. Biomed Chromatogr. 2008 Mar;22(3):260-4. PubMed PMID: 17939167.
3: Tanaka K, Urata N, Mikami M, Ogasawara M, Matsunaga T, Terashima N, Suzuki H. Effect of iguratimod and other anti-rheumatic drugs on adenocarcinoma colon 26-induced cachexia in mice. Inflamm Res. 2007 Jan;56(1):17-23. PubMed PMID: 17334666.
4: Hara M, Abe T, Sugawara S, Mizushima Y, Hoshi K, Irimajiri S, Hashimoto H, Yoshino S, Matsui N, Nobunaga M. Long-term safety study of iguratimod in patients with rheumatoid arthritis. Mod Rheumatol. 2007;17(1):10-6. Epub 2007 Feb 20. PubMed PMID: 17278016.
5: Hara M, Abe T, Sugawara S, Mizushima Y, Hoshi K, Irimajiri S, Hashimoto H, Yoshino S, Matsui N, Nobunaga M, Nakano S. Efficacy and safety of iguratimod compared with placebo and salazosulfapyridine in active rheumatoid arthritis: a controlled, multicenter, double-blind, parallel-group study. Mod Rheumatol. 2007;17(1):1-9. Epub 2007 Feb 20. PubMed PMID: 17278015.
6: Jiang Y, Lü W, Yu SQ, Yao L, Xu GL, Zhang XR. [Inhibitory effect of iguratimod on TNFalpha production and NF-kappaB activity in LPS-stimulated rat alveolar macrophage cell line]. Yao Xue Xue Bao. 2006 May;41(5):401-5. Chinese. PubMed PMID: 16848314.
7: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jul-Aug;26(6):473-503. PubMed PMID: 15349141.
8: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 May;26(4):295-318. PubMed PMID: 15319808.
