Iguratimod: Difference between revisions

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{{Short description|Overview of the drug Iguratimod}}
{{Drugbox
{{Drugbox
| drug_name =
| image = Iguratimod.svg
| IUPAC_name        = ''N''-(3-Formamido-4-oxo-6-phenoxy-4''H''-chromen-7-yl)methanesulfonamide
| image_size = 250px
| image             = Iguratimod.svg
| image_alt = Chemical structure of Iguratimod
| alt              =
| caption          =
 
<!-- Clinical data -->
| tradename        = Careram; Kolbet
| Drugs.com        =
| MedlinePlus      =
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      = <!-- A / B            / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status      =  
| routes_of_administration =
 
<!-- Pharmacokinetic data -->
| bioavailability  =
| protein_bound    =
| metabolism        =
| elimination_half-life =
| excretion        =
 
<!-- Identifiers -->
| CAS_number        = 123663-49-0
| ATCvet            =
| ATC_prefix        = None
| ATC_suffix        =
| DrugBank          =
| PubChem          = 124246
| ChemSpiderID      = 110694
| ChEMBL = 2107455
| synonyms          = T-614
 
<!-- Chemical data -->
| C=17 | H=14 | N=2 | O=6 | S=1
| molecular_weight  = 374.368 g/mol
| smiles            = O=S(=O)(Nc3c(Oc1ccccc1)cc2c(O/C=C(\C2=O)NC=O)c3)C
| StdInChI          = 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)
| StdInChIKey      = ANMATWQYLIFGOK-UHFFFAOYSA-N
}}
}}


'''Iguratimod''' is an [[anti-inflammatory]] small molecule drug used for the treatment of [[rheumatoid arthritis]], together with [[methotrexate]] in Japan and China.<ref name=Tanaka2015>{{cite journal|last1=Tanaka|first1=K|last2=Yamaguchi|first2=T|last3=Hara|first3=M|title=Iguratimod for the treatment of rheumatoid arthritis in Japan.|journal=Expert review of clinical immunology|date=May 2015|volume=11|issue=5|pages=565–73|doi=10.1586/1744666X.2015.1027151|pmid=25797025}}</ref>  As of 2015 the [[biological target]] was not known, but it prevents [[NF-κB]] activation and subsequently selectively inhibits [[COX-2]] and several inflammatory [[cytokine]]s.<ref name=Tanaka2015/>
'''Iguratimod''' is a [[disease-modifying antirheumatic drug]] (DMARD) used primarily in the treatment of [[rheumatoid arthritis]]. It is known for its anti-inflammatory and immunomodulatory effects. Iguratimod is particularly noted for its ability to inhibit the production of inflammatory cytokines and the activation of [[nuclear factor kappa-light-chain-enhancer of activated B cells|NF-_B]].


Adverse effects include [[Elevated transaminases]], nausea, vomiting, stomach pain; rashes, and itchiness.<ref name=Tanaka2015/>
==Mechanism of Action==
Iguratimod works by modulating the immune response. It inhibits the production of pro-inflammatory cytokines such as [[tumor necrosis factor alpha|TNF-_]], [[interleukin-1|IL-1]], and [[interleukin-6|IL-6]]. Additionally, it suppresses the activation of NF-_B, a transcription factor that plays a key role in the inflammatory response. This dual action helps reduce inflammation and slow the progression of joint damage in rheumatoid arthritis.


It is a derivative of 7-methanesulfonylamino-6-phenoxychromones and is a [[chromone]] with two amide groups; it was first published in 2000.<ref name=Tanaka2015/><ref>{{cite journal|last1=Inaba|first1=T|last2=Tanaka|first2=K|last3=Takeno|first3=R|last4=Nagaki|first4=H|last5=Yoshida|first5=C|last6=Takano|first6=S|title=Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6-phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models.|journal=Chemical & Pharmaceutical Bulletin|date=January 2000|volume=48|issue=1|pages=131–9|pmid=10705489|url=https://www.jstage.jst.go.jp/article/cpb1958/48/1/48_1_131/_pdf/-char/en}}</ref>  It was submitted for regulatory approval in Japan in 2003; the application was withdrawn in 2009, and it was resubmitted with additional data in 2011 and approved for marketing in Japan in 2012.<ref name=Tanaka2015/> [[Eisai (company)|Eisai]] and [[Toyama Chemical]] market it in Japan.<ref>{{cite journal|last1=Bronson|first1=J|last2=Dhar|first2=M|last3=Ewing|first3=W|last4=Lonberg|first4=N|title=Chapter Thirty-One – To Market, To Market—2011|journal=Annual Reports in Medicinal Chemistry|date=2012|volume=47|pages=499–569|doi=10.1016/B978-0-12-396492-2.00031-X}}</ref> Approval was obtained in China in 2011 by Simcere, independently of the Japanese originators.<ref name=Tanaka2015/><ref>{{cite web|title=Iguratimod - Simcere|url=https://adisinsight.springer.com/drugs/800032226|publisher=AdisInsight|accessdate=27 May 2018|language=en}}</ref>
==Pharmacokinetics==
Iguratimod is administered orally and is absorbed through the gastrointestinal tract. It undergoes hepatic metabolism and is excreted primarily in the urine. The drug has a half-life that allows for once-daily dosing, which can improve patient compliance.


During discovery and development it was called T-614 and it is marketed under the names Careram and Kolbet.<ref>{{cite web|title=Iguratimod - Toyama Chemical|url=https://adisinsight.springer.com/drugs/800001541|publisher=AdisInsight|accessdate=27 May 2018|language=en}}</ref>
==Clinical Use==
Iguratimod is used in the management of rheumatoid arthritis, particularly in patients who have not responded adequately to other DMARDs. It can be used as monotherapy or in combination with other antirheumatic drugs such as [[methotrexate]].


==References==
==Side Effects==
{{reflist}}
Common side effects of iguratimod include gastrointestinal disturbances, such as nausea and diarrhea, as well as liver enzyme elevations. Patients on iguratimod require regular monitoring of liver function tests. Less commonly, it may cause [[leukopenia]] or [[thrombocytopenia]].


[[Category:Sulfonamides]]
==Contraindications==
[[Category:Anti-inflammatory and antirheumatic products]]
Iguratimod is contraindicated in patients with known hypersensitivity to the drug. It should be used with caution in patients with liver impairment or a history of liver disease.
[[Category:Chromones]]
[[Category:Formamides]]


==Related Pages==
* [[Rheumatoid arthritis]]
* [[Disease-modifying antirheumatic drug]]
* [[Cytokine]]
* [[Nuclear factor kappa-light-chain-enhancer of activated B cells]]


{{antineoplastic-drug-stub}}
[[Category:Antirheumatic agents]]
{{dictionary-stub1}}
[[Category:Immunosuppressants]]

Revision as of 03:29, 13 February 2025

Overview of the drug Iguratimod


Iguratimod
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number
PubChem
DrugBank
ChemSpider
KEGG


Iguratimod is a disease-modifying antirheumatic drug (DMARD) used primarily in the treatment of rheumatoid arthritis. It is known for its anti-inflammatory and immunomodulatory effects. Iguratimod is particularly noted for its ability to inhibit the production of inflammatory cytokines and the activation of NF-_B.

Mechanism of Action

Iguratimod works by modulating the immune response. It inhibits the production of pro-inflammatory cytokines such as TNF-_, IL-1, and IL-6. Additionally, it suppresses the activation of NF-_B, a transcription factor that plays a key role in the inflammatory response. This dual action helps reduce inflammation and slow the progression of joint damage in rheumatoid arthritis.

Pharmacokinetics

Iguratimod is administered orally and is absorbed through the gastrointestinal tract. It undergoes hepatic metabolism and is excreted primarily in the urine. The drug has a half-life that allows for once-daily dosing, which can improve patient compliance.

Clinical Use

Iguratimod is used in the management of rheumatoid arthritis, particularly in patients who have not responded adequately to other DMARDs. It can be used as monotherapy or in combination with other antirheumatic drugs such as methotrexate.

Side Effects

Common side effects of iguratimod include gastrointestinal disturbances, such as nausea and diarrhea, as well as liver enzyme elevations. Patients on iguratimod require regular monitoring of liver function tests. Less commonly, it may cause leukopenia or thrombocytopenia.

Contraindications

Iguratimod is contraindicated in patients with known hypersensitivity to the drug. It should be used with caution in patients with liver impairment or a history of liver disease.

Related Pages

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