Iguratimod
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 315227

CAS#: 123663-49-0

Description: Iguratimod is one of a series of 4H-1-benzopyran-4-ones which has potent anti-inflammatory, analgesic and antipyretic activity. The drug is a selective inhibitor of cyclo-oxygenase-2 (COX-2), and inhibits the production of interleukin-1 (IL-1), IL-6, IL-8 and tumour necrosis factor. Iguratimod is currently under clinical trials ( http://www.simcere.com/english/r&d/Pipeline.asp).


Chemical Structure

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Iguratimod
CAS# 123663-49-0

Theoretical Analysis

MedKoo Cat#: 315227
Name: Iguratimod
CAS#: 123663-49-0
Chemical Formula: C17H14N2O6S
Exact Mass: 374.06
Molecular Weight: 374.367
Elemental Analysis: C, 54.54; H, 3.77; N, 7.48; O, 25.64; S, 8.57

Price and Availability

Size Price Availability Quantity
50mg USD 350 2 Weeks
100mg USD 550 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1850 2 Weeks
1g USD 3250 2 Weeks
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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

Appearance: Solid powder

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

Product Data:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 14.0 37.40
DMSO 33.1 88.44
PBS (pH 7.2) 0.3 0.67

Preparing Stock Solutions

The following data is based on the product molecular weight 374.367000000000000000000000000000 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.

Recalculate based on batch purity %
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.

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 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.