IGURATIMOD
Iguratimod
CAS: 123663-49-0
Molecular Formula: C17H14N2O6S
IGURATIMOD - Names and Identifiers
| Name | Iguratimod |
| Synonyms | T 614 Ailamode Iguratimod IGURATIMOD IguratiMod (T 614) N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide N-(7-(MethylsulfonaMido)-4-oxo-6-phenoxy-4H-chroMen-3-yl)forMaMide N-[3-(formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide 3-(Formylamino)-7-(methylsulfonylamino)-6-phenoxy-4H-1-benzopyran-4-one N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide |
| CAS | 123663-49-0 |
| EINECS | 808-127-0 |
| InChI | InChI=1/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) |
IGURATIMOD - Physico-chemical Properties
| Molecular Formula | C17H14N2O6S |
| Molar Mass | 374.37 |
| Density | 1.52±0.1 g/cm3(Predicted) |
| Melting Point | 238.0 to 242.0 °C |
| Boling Point | 580.6±60.0 °C(Predicted) |
| Flash Point | 304.9°C |
| Solubility | DMSO (Slightly) |
| Vapor Presure | 1.8E-13mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 5.58±0.20(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 1.673 |
| In vitro study | Iguratimod (T-614) is an antirheumatic agent, acts as an inhibitor of COX-2, with an IC 50 of 20 μM (7.7 μg/mL), but shows no effect on COX-1. Iguratimod (0.1, 1, 10 μg/mL) inhibits bradykinin-stimulated PGE2 release from fibroblasts. Iguratimod suppresses the COX activity from bradykinin stimulated fibroblasts in a concentration-dependent manner, with an IC 50 of 48 μg/mL. Iguratimod (10 and 30 μg/mL) also dose-dependently inhibits COX-2 mRNA levels. In addition, Iguratimod potently inhibits macrophage migration inhibitory factor (MIF) with an IC 50 of 6.81 μM. Iguratimod is synergetic with glucocorticoids in vitro. |
| In vivo study | Iguratimod (5 or 20 mg/kg) shows analgesic effect, significantly improves the pain withdrawal threshold of the left hind paw in dose-dependent manner in rats. Iguratimod (5 or 20 mg/kg) reduces the elevation of pERK1/2 and c-Fos in the spinal cord induced by cancer cell inoculation. Iguratimod also dose-dependently decreases the IL-6 levels in rats. In Iguratimod-treated rats, the activity of osteoclasts is weaker than the control group. Iguratimod (20 mg/kg i.p.) shows significantly increased survival in BALB/c mice that are vulnerable to endotoxemia, and attenuates TNFα release measured in serum isolated 90 min post-LPS administration in wild-type C57BL/6 mice. |
IGURATIMOD - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.671 ml | 13.356 ml | 26.712 ml |
| 5 mM | 0.534 ml | 2.671 ml | 5.342 ml |
| 10 mM | 0.267 ml | 1.336 ml | 2.671 ml |
| 5 mM | 0.053 ml | 0.267 ml | 0.534 ml |
Last Update：2024-01-02 23:10:35
IGURATIMOD - Reference Information
| Antirheumatic drug | Ilamod, the chemical name is N-[3-(formamido)-4-oxo-6-phenoxy -4H-1-benzopyran-7-yl] methanesulfonamide, the appearance is white or white-like crystalline powder, odorless, odorless, insoluble in water, slightly soluble in acetonitrile, soluble in methylene chloride, tetrahydrobaran, chloroform and ethanol, etc. It is a new type of anti-rheumatic drug for disease relief, which can relieve joint damage and immune abnormalities in chronic arthritis and autoimmune diseases, and inhibit the production of inflammatory cytokines and immunoglobulins. It has significant effect and safety in the treatment of rheumatoid arthritis. It shows anti-inflammatory and analgesic effects on acute and chronic inflammation. Different from traditional non-steroidal anti-inflammatory drugs, Iramod basically does not show ulcers in the digestive tract. Adverse reactions, this product can activate osteoclasts, promote bone resorption, and lead to bone loss. Inhibiting these proinflammatory factors can play a dual effect of controlling rheumatoid arthritis and causing bone loss. In August 2011, Jiangsu xiansheng pharmaceutical co., ltd was approved by the state food and drug administration (SFDA) to develop and produce elamod (iguratimod). |
| Mechanism of action | The main mechanism of action of Ilamod is: selectively inhibiting cyclooxygenase-2 to reduce the production of prostaglandins in inflammatory tissues; Inhibit the release of bradykinin from inflammatory tissues; Inhibit antigen-specific T cell proliferation; Reduce the level of proinflammatory factors produced by B cells in patients with rheumatoid arthritis; Stimulate osteoblast differentiation and bone construction; inhibition of synovial cell co-stimulatory factor expression and cytokine production. It can inhibit immunoglobulin production, inhibit cytokine production, inhibit bone resorption and promote bone formation. It can inhibit the increase of bradykinin in the inflammatory reaction induced by kaolin, and its analgesic effect may be related to the inhibition of bradykinin. |
| Synthetic route | The nucleophilic substitution reaction between 4-chloro-3-nitroanisole (2) and phenoxy anion is followed by iron powder reduction, methanesulfonylation, acylation, Geitmann-Koch reaction, methoxy hydrolysis, and cyclization. Figure 1 shows the synthetic route of Ilamod, which: 3) 4-phenoxy -3-nitroanisole; 4) 4-phenoxy -3-aminobanisole; 5) 4-phenoxy-3-methylsulfonylaminobanisole; 6)N-[4 -(2-aminoacetyl)-5-methoxy-2-phenoxylphenyl] methanesulfonamide hydrochloride; 7)N-[4 -(2-formylaminoacetyl)-5-methoxy-2-phenoxyphenyl] methanesulfonamide; 8)N-[4 -(2-formylaminoacetyl)-5-phenolhydroxy-2-phenoxyphenyl] methanesulfonamide. |
| Pharmacokinetics | Studies have shown that Ilamod conforms to the primary pharmacokinetic characteristics of a one-compartment model in the body, and its content in the liver, kidney and uterus is the highest, and the brain content is the lowest. (2016-01-22) |
| adverse reactions | this product has high safety and no serious adverse reactions. the discomfort symptoms are mainly mild gastrointestinal discomfort, and the symptoms are not serious. after appropriate treatment, it will not affect the patients to continue treatment. |
| biological activity | Iguratimod is an anti-rheumatic agent that can effectively inhibit the activity of COX-2 with an IC50 value of 20 μM (7.7 μg/mL), but has no effect on COX-1. Iguratimod is also an inhibitor of macrophage migration inhibitory factor (MIF) with an IC50 value of 6.81 μM. |
Last Update：2024-04-10 22:29:15
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CAS: 123663-49-0
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