MedKoo Biosciences

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

Iguratimod

CAS# 123663-49-0

Product data Instruction

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
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
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Product Data

Instruction:

View handling instruction

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.

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, LÃ¼ 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.

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