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MedKoo Cat#: 540225 | Name: Irsogladine maleate
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Description:

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

Irsogladine maleate is an inhibitor of COX-1/2 and PDE. It decreases NSAID-induced mucosal injury, prevents fibrosis, and facilitates gap junction communication.

Chemical Structure

Irsogladine maleate
Irsogladine maleate
CAS#84504-69-8 (maleate)

Theoretical Analysis

MedKoo Cat#: 540225

Name: Irsogladine maleate

CAS#: 84504-69-8 (maleate)

Chemical Formula: C13H11Cl2N5O4

Exact Mass:

Molecular Weight: 372.16

Elemental Analysis: C, 41.96; H, 2.98; Cl, 19.05; N, 18.82; O, 17.20

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00
500mg USD 700.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
57381-26-7 (free base) 84504-69-8 (maleate)
Synonym
Gaslon; Irsogladine maleate; MN-1695; MN1695; MN 1695.
IUPAC/Chemical Name
6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine maleate
InChi Key
PJLVTVAIERNDEQ-BTJKTKAUSA-N
InChi Code
InChI=1S/C9H7Cl2N5.C4H4O4/c10-4-1-2-6(11)5(3-4)7-14-8(12)16-9(13)15-7;5-3(6)1-2-4(7)8/h1-3H,(H4,12,13,14,15,16);1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code
ClC1=CC=C(Cl)C(C2=NC(N)=NC(N)=N2)=C1.O=C(O)/C=C\C(O)=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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Irsogladine is a PDE4 inhibitor and muscarinic acetylcholine receptor binder.
In vitro activity:
Irsogladine maleate (IM) counters Aggregatibacter actinomycetemcomitans-induced reduction of the gap junction intercellular communication and the expression of zonula occludens-1, which is a major tight junction structured protein, in cultured human gingival epithelial cells (HGEC). In addition, IM obviates the A. actinomycetemcomitans-induced increase in interleukin (IL)-8 levels in HGEC. Reference: Biochem Pharmacol. 2010 May 15;79(10):1496-505. https://pubmed.ncbi.nlm.nih.gov/20096665/
In vivo activity:
Mice were pretreated with IM for 1 hours before ulcer induction. IM (irsogladine maleate) significantly reduced the extent of ethanol/HCl mixture-induced gastric ulceration. Reference: Korean J Intern Med. 2021 Jan;36(1):67-75. https://pubmed.ncbi.nlm.nih.gov/31852177/
Solvent mg/mL mM
Solubility
DMF 30.0 80.61
DMSO 30.0 80.61
DMSO:PBS (pH 7.2) (1:3) 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 372.16 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. Fujita T, Kishimoto A, Shiba H, Hayashida K, Kajiya M, Uchida Y, Matsuda S, Takeda K, Ouhara K, Kawaguchi H, Abiko Y, Kurihara H. Irsogladine maleate regulates neutrophil migration and E-cadherin expression in gingival epithelium stimulated by Aggregatibacter actinomycetemcomitans. Biochem Pharmacol. 2010 May 15;79(10):1496-505. doi: 10.1016/j.bcp.2010.01.017. Epub 2010 Jan 22. PMID: 20096665. 2. Yao J, Zhu Y, Sun W, Sawada N, Hiramatsu N, Takeda M, Kitamura M. Irsogladine maleate potentiates the effects of nitric oxide on activation of cAMP signalling pathways and suppression of mesangial cell mitogenesis. Br J Pharmacol. 2007 Jun;151(4):457-66. doi: 10.1038/sj.bjp.0707255. Epub 2007 Apr 16. PMID: 17435794; PMCID: PMC2013962. 3. Kwon SC, Kim JH. Gastroprotective effects of irsogladine maleate on ethanol/hydrochloric acid induced gastric ulcers in mice. Korean J Intern Med. 2021 Jan;36(1):67-75. doi: 10.3904/kjim.2018.290. Epub 2019 Dec 20. PMID: 31852177; PMCID: PMC7820653. 4. Onuma W, Tomono S, Miyamoto S, Fujii G, Hamoya T, Fujimoto K, Miyoshi N, Fukai F, Wakabayashi K, Mutoh M. Irsogladine maleate, a gastric mucosal protectant, suppresses intestinal polyp development in Apc-mutant mice. Oncotarget. 2016 Feb 23;7(8):8640-52. doi: 10.18632/oncotarget.7082. PMID: 26840084; PMCID: PMC4890993.
In vitro protocol:
1. Fujita T, Kishimoto A, Shiba H, Hayashida K, Kajiya M, Uchida Y, Matsuda S, Takeda K, Ouhara K, Kawaguchi H, Abiko Y, Kurihara H. Irsogladine maleate regulates neutrophil migration and E-cadherin expression in gingival epithelium stimulated by Aggregatibacter actinomycetemcomitans. Biochem Pharmacol. 2010 May 15;79(10):1496-505. doi: 10.1016/j.bcp.2010.01.017. Epub 2010 Jan 22. PMID: 20096665. 2. Yao J, Zhu Y, Sun W, Sawada N, Hiramatsu N, Takeda M, Kitamura M. Irsogladine maleate potentiates the effects of nitric oxide on activation of cAMP signalling pathways and suppression of mesangial cell mitogenesis. Br J Pharmacol. 2007 Jun;151(4):457-66. doi: 10.1038/sj.bjp.0707255. Epub 2007 Apr 16. PMID: 17435794; PMCID: PMC2013962.
In vivo protocol:
1. Kwon SC, Kim JH. Gastroprotective effects of irsogladine maleate on ethanol/hydrochloric acid induced gastric ulcers in mice. Korean J Intern Med. 2021 Jan;36(1):67-75. doi: 10.3904/kjim.2018.290. Epub 2019 Dec 20. PMID: 31852177; PMCID: PMC7820653. 2. Onuma W, Tomono S, Miyamoto S, Fujii G, Hamoya T, Fujimoto K, Miyoshi N, Fukai F, Wakabayashi K, Mutoh M. Irsogladine maleate, a gastric mucosal protectant, suppresses intestinal polyp development in Apc-mutant mice. Oncotarget. 2016 Feb 23;7(8):8640-52. doi: 10.18632/oncotarget.7082. PMID: 26840084; PMCID: PMC4890993.
1: Onuma W, Tomono S, Miyamoto S, Fujii G, Hamoya T, Fujimoto K, Miyoshi N, Fukai F, Wakabayashi K, Mutoh M. Irsogladine maleate, a gastric mucosal protectant, suppresses intestinal polyp development in Apc-mutant mice. Oncotarget. 2016 Feb 23;7(8):8640-52. doi: 10.18632/oncotarget.7082. PubMed PMID: 26840084; PubMed Central PMCID: PMC4890993. 2: Hayashi N, George J, Shiroeda H, Saito T, Toshikuni N, Tsuchishima M, Arisawa T, Tsutsumi M. Irsogladine maleate for the treatment of recurrent aphthous stomatitis in hepatitis C virus patients on pegylated-interferon and ribavirin: a pilot study. J Gastroenterol Hepatol. 2013 Jun;28(6):1015-8. doi: 10.1111/jgh.12137. PubMed PMID: 23425065. 3: Nakagawa T, Katsuno T, Noguchi Y, Mandai Y, Yoshihama S, Saito K, Maruoka D, Matsumura T, Arai M, Yokosuka O. Irsogladine Maleate Prevents Colitis in Interleukin-10 Gene-Deficient Mice by Reducing Interleukin-12 and -23 Production. Biol Pharm Bull. 2015;38(11):1681-8. doi: 10.1248/bpb.b15-00189. PubMed PMID: 26521820. 4: Nomura M, Kamata M, Kojima H, Hayashi K, Sawada S. Irsogladine maleate reduces the incidence of fluorouracil-based chemotherapy-induced oral mucositis. Ann Oncol. 2013 Apr;24(4):1062-6. doi: 10.1093/annonc/mds584. Epub 2012 Nov 14. PubMed PMID: 23152361. 5: Suzuki T, Matsushima M, Masui A, Tsuda S, Imai J, Nakamura J, Tsukune Y, Uchida T, Yuhara H, Igarashi M, Koike J, Mine T. Irsogladine maleate and rabeprazole in non-erosive reflux disease: A double-blind, placebo-controlled study. World J Gastroenterol. 2015 Apr 28;21(16):5023-31. doi: 10.3748/wjg.v21.i16.5023. PubMed PMID: 25945018; PubMed Central PMCID: PMC4408477. 6: Miyata R, Nomura K, Kakuki T, Takano K, Kohno T, Konno T, Sawada N, Himi T, Kojima T. Irsogladine maleate regulates gap junctional intercellular communication-dependent epithelial barrier in human nasal epithelial cells. J Membr Biol. 2015 Apr;248(2):327-36. doi: 10.1007/s00232-015-9774-0. Epub 2015 Feb 5. PubMed PMID: 25652184. 7: Savitri IJ, Ouhara K, Fujita T, Kajiya M, Miyagawa T, Kittaka M, Yamakawa M, Shiba H, Kurihara H. Irsogladine maleate inhibits Porphyromonas gingivalis-mediated expression of toll-like receptor 2 and interleukin-8 in human gingival epithelial cells. J Periodontal Res. 2015 Aug;50(4):486-93. doi: 10.1111/jre.12231. Epub 2014 Sep 20. PubMed PMID: 25244303. 8: Miyagawa T, Fujita T, Ouhara K, Matsuda S, Kajiya M, Hayashida K, Imai H, Yoshimoto T, Iwata T, Shiba H, Abiko Y, Kurihara H. Irsogladine maleate regulates the inflammatory related genes in human gingival epithelial cells stimulated by Aggregatibacter actinomycetemcomitans. Int Immunopharmacol. 2013 Feb;15(2):340-7. doi: 10.1016/j.intimp.2012.12.011. Epub 2013 Jan 8. PubMed PMID: 23306101. 9: Yamaguchi H, Suzuki K, Nagata M, Kawase T, Sukumaran V, Thandavarayan RA, Kawauchi Y, Yokoyama J, Tomita M, Kawachi H, Watanabe K, Yoneyama H, Asakura H, Takagi R. Irsogladine maleate ameliorates inflammation and fibrosis in mice with chronic colitis induced by dextran sulfate sodium. Med Mol Morphol. 2012 Jun;45(3):140-51. Epub 2012 Sep 22. PubMed PMID: 23001296. 10: Sagawa M, Shibuya J, Takahashi S, Endo C, Abiko M, Suzuki H, Matsumura Y, Sakuma T, Sato N, Deguchi H, Nakamura Y, Hasumi T, Kondo T. A randomized phase III trial of postoperative adjuvant therapy for completely resected stage IA-IIIA lung cancer using an anti angiogenetic agent: irsogladine maleate. Minerva Chir. 2013 Dec;68(6):587-97. PubMed PMID: 24193291. 11: Fujita T, Yumoto H, Shiba H, Ouhara K, Miyagawa T, Nagahara T, Matsuda S, Kawaguchi H, Matsuo T, Murakami S, Kurihara H. Irsogladine maleate regulates epithelial barrier function in tumor necrosis factor-α-stimulated human gingival epithelial cells. J Periodontal Res. 2012 Feb;47(1):55-61. doi: 10.1111/j.1600-0765.2011.01404.x. Epub 2011 Sep 6. PubMed PMID: 21895660. 12: Murakami K, Okimoto T, Kodama M, Tanahashi J, Mizukami K, Shuto M, Abe H, Arita T, Fujioka T. Comparison of the efficacy of irsogladine maleate and famotidine for the healing of gastric ulcers after Helicobacter pylori eradication therapy: a randomized, controlled, prospective study. Scand J Gastroenterol. 2011 Mar;46(3):287-92. doi: 10.3109/00365521.2010.531485. Epub 2010 Nov 14. PubMed PMID: 21073372. 13: Hiraishi H, Haruma K, Miwa H, Goto H. Clinical trial: irsogladine maleate, a mucosal protective drug, accelerates gastric ulcer healing after treatment for eradication of Helicobacter pylori infection--the results of a multicentre, double-blind, randomized clinical trial (IMPACT study). Aliment Pharmacol Ther. 2010 Apr;31(8):824-33. doi: 10.1111/j.1365-2036.2010.04250.x. Epub 2010 Feb 2. PubMed PMID: 20132152. 14: Akagi M, Amagase K, Murakami T, Takeuchi K. Irsogladine: overview of the mechanisms of mucosal protective and healing- promoting actions in the gastrointestinal tract. Curr Pharm Des. 2013;19(1):106-14. Review. PubMed PMID: 22950502. 15: Zhang X, Tajima K, Kageyama K, Kyoi T. Irsogladine maleate suppresses indomethacin-induced elevation of proinflammatory cytokines and gastric injury in rats. World J Gastroenterol. 2008 Aug 14;14(30):4784-90. PubMed PMID: 18720540; PubMed Central PMCID: PMC2739341. 16: Hosokawa T, Ogawa K, Otani Y, Kajiwara T. 2 cases of gastric-cancer remarkably reduced with a combined dosage of irsogladine maleate preparation and uft. Oncol Rep. 1994 Jan;1(1):93-5. PubMed PMID: 21607313. 17: Matsumoto T, Sakurai K, Tanaka A, Ishibashi T, Tachibana K, Ishikawa K, Yokote K. The anti-ulcer agent, irsogladine, increases insulin secretion by MIN6 cells. Eur J Pharmacol. 2012 Jun 15;685(1-3):213-7. doi: 10.1016/j.ejphar.2012.04.005. Epub 2012 Apr 20. PubMed PMID: 22542662. 18: Isomura Y, Yamaji Y, Yamada A, Watanabe Y, Suzuki H, Kobayashi Y, Yoshida S, Watabe H, Hirata Y, Yoshida H, Koike K. Irsogladine improves small-intestinal injuries in regular users of nonsteroidal anti-inflammatory drugs. Gastrointest Endosc. 2014 Jul;80(1):118-25. doi: 10.1016/j.gie.2013.12.030. Epub 2014 Feb 8. PubMed PMID: 24518124. 19: Inui M, Nakase M, Okumura K, Nakamura S, Tagawa T. Irsogladine Maleate in the management of recurrent aphthous stomatitis: a pilot study. Spec Care Dentist. 2010 Mar-Apr;30(2):33-4. doi: 10.1111/j.1754-4505.2009.00130.x. PubMed PMID: 20415798. 20: Kurishita A, Takai Y, Ueda F, Sakamoto K, Ono T. Post-irradiation protective effect of irsogladine maleate on intestinal crypt stem cells in mice. Strahlenther Onkol. 1992 Dec;168(12):728-31. PubMed PMID: 1481123.