WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 407105
CAS#: 870087-36-8 (mesylate)
Description: Apilimod, also known as STA-5326, is a IL-12/IL-23 inhibitor. Apilimod inhibits IL-12 and IL-23 production - cytokines that are involved in autoimmune diseases - through the prevention of nuclear translocation of c-Rel. Synta Pharmaceuticals Corp is developing apilimod for the potential treatment of Crohn's disease (CD) and other autoimmune diseases. Preclinical studies demonstrated the successful inhibition of IL-12 and IL-23 production by the drug.
MedKoo Cat#: 407105
Name: Apilimod mesylate
CAS#: 870087-36-8 (mesylate)
Chemical Formula: C25H34N6O8S2
Exact Mass:
Molecular Weight: 610.7
Elemental Analysis: C, 49.17; H, 5.61; N, 13.76; O, 20.96; S, 10.50
Related CAS #: 870087-36-8 (mesylate) 541550-19-0 (free base) 1383916-59-3 (free base) 870087-37-9 (HCl) 870151-86-3 (tosylate) 870087-41-5 (besylate)
Synonym: STA-5326; STA5326; STA 5326; LAM-002; LAM 002; LAM002; Apilimod; Apilimod mesylate.
IUPAC/Chemical Name: (E)-4-(6-(2-(3-methylbenzylidene)hydrazinyl)-2-(2-(pyridin-2-yl)ethoxy)pyrimidin-4-yl)morpholine dimethanesulfonate
InChi Key: GAJWNIKZLYZYSY-OKUPSQOASA-N
InChi Code: InChI=1S/C23H26N6O2.2CH4O3S/c1-18-5-4-6-19(15-18)17-25-28-21-16-22(29-10-13-30-14-11-29)27-23(26-21)31-12-8-20-7-2-3-9-24-20;2*1-5(2,3)4/h2-7,9,15-17H,8,10-14H2,1H3,(H,26,27,28);2*1H3,(H,2,3,4)/b25-17+;;
SMILES Code: CC1=CC(/C=N/NC2=CC(N3CCOCC3)=NC(OCCC4=NC=CC=C4)=N2)=CC=C1.CS(=O)(O)=O.CS(=O)(O)=O
Appearance: White to off-white 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, not in water
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
The following data is based on the product molecular weight 610.7 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 |
1: Cai X, Xu Y, Kim YM, Loureiro J, Huang Q. PIKfyve, a class III lipid kinase, is required for TLR-induced type I IFN production via modulation of ATF3. J Immunol. 2014 Apr 1;192(7):3383-9. doi: 10.4049/jimmunol.1302411. Epub 2014 Mar 5. PubMed PMID: 24600036.
2: Cai X, Xu Y, Cheung AK, Tomlinson RC, Alcázar-Román A, Murphy L, Billich A, Zhang B, Feng Y, Klumpp M, Rondeau JM, Fazal AN, Wilson CJ, Myer V, Joberty G, Bouwmeester T, Labow MA, Finan PM, Porter JA, Ploegh HL, Baird D, De Camilli P, Tallarico JA, Huang Q. PIKfyve, a class III PI kinase, is the target of the small molecular IL-12/IL-23 inhibitor apilimod and a player in Toll-like receptor signaling. Chem Biol. 2013 Jul 25;20(7):912-21. doi: 10.1016/j.chembiol.2013.05.010. PubMed PMID: 23890009.
3: Baird AM, Dockry E, Daly A, Stack E, Doherty DG, O'Byrne KJ, Gray SG. IL-23R is Epigenetically Regulated and Modulated by Chemotherapy in Non-Small Cell Lung Cancer. Front Oncol. 2013 Jun 19;3:162. doi: 10.3389/fonc.2013.00162. eCollection 2013. PubMed PMID: 23802098; PubMed Central PMCID: PMC3685824.
4: Wada Y, Cardinale I, Khatcherian A, Chu J, Kantor AB, Gottlieb AB, Tatsuta N, Jacobson E, Barsoum J, Krueger JG. Apilimod inhibits the production of IL-12 and IL-23 and reduces dendritic cell infiltration in psoriasis. PLoS One. 2012;7(4):e35069. doi: 10.1371/journal.pone.0035069. Epub 2012 Apr 6. PubMed PMID: 22493730; PubMed Central PMCID: PMC3320873.
5: Krausz S, Boumans MJ, Gerlag DM, Lufkin J, van Kuijk AW, Bakker A, de Boer M, Lodde BM, Reedquist KA, Jacobson EW, O'Meara M, Tak PP. Brief report: a phase IIa, randomized, double-blind, placebo-controlled trial of apilimod mesylate, an interleukin-12/interleukin-23 inhibitor, in patients with rheumatoid arthritis. Arthritis Rheum. 2012 Jun;64(6):1750-5. doi: 10.1002/art.34339. Epub 2011 Dec 14. PubMed PMID: 22170479.
6: Kurzeja M, Rudnicka L, Olszewska M. New interleukin-23 pathway inhibitors in dermatology: ustekinumab, briakinumab, and secukinumab. Am J Clin Dermatol. 2011 Apr 1;12(2):113-25. doi: 10.2165/11538950-000000000-00000. Review. PubMed PMID: 21348542.
7: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Dec;32(10):749-73. doi: 10.1358/mf.2010.32.10.1573763. PubMed PMID: 21225012.
8: Keino H. [Therapeutic effect of the low molecular weight inhibitor of the NF-kappaB signaling pathway on experimental autoimmune uveoretinitis]. Nippon Ganka Gakkai Zasshi. 2010 Nov;114(11):944-54. Review. Japanese. PubMed PMID: 21141074.
9: Sands BE, Jacobson EW, Sylwestrowicz T, Younes Z, Dryden G, Fedorak R, Greenbloom S. Randomized, double-blind, placebo-controlled trial of the oral interleukin-12/23 inhibitor apilimod mesylate for treatment of active Crohn's disease. Inflamm Bowel Dis. 2010 Jul;16(7):1209-18. doi: 10.1002/ibd.21159. PubMed PMID: 19918967.
10: Keino H, Watanabe T, Sato Y, Niikura M, Wada Y, Okada AA. Therapeutic effect of the potent IL-12/IL-23 inhibitor STA-5326 on experimental autoimmune uveoretinitis. Arthritis Res Ther. 2008;10(5):R122. doi: 10.1186/ar2530. Epub 2008 Oct 13. PubMed PMID: 18847496; PubMed Central PMCID: PMC2592812.
11: Billich A. Drug evaluation: apilimod, an oral IL-12/IL-23 inhibitor for the treatment of autoimmune diseases and common variable immunodeficiency. IDrugs. 2007 Jan;10(1):53-9. PubMed PMID: 17187316.
12: Wada Y, Lu R, Zhou D, Chu J, Przewloka T, Zhang S, Li L, Wu Y, Qin J, Balasubramanyam V, Barsoum J, Ono M. Selective abrogation of Th1 response by STA-5326, a potent IL-12/IL-23 inhibitor. Blood. 2007 Feb 1;109(3):1156-64. Epub 2006 Oct 19. PubMed PMID: 17053051.
13: Burakoff R, Barish CF, Riff D, Pruitt R, Chey WY, Farraye FA, Shafran I, Katz S, Krone CL, Vander Vliet M, Stevens C, Sherman ML, Jacobson E, Bleday R. A phase 1/2A trial of STA 5326, an oral interleukin-12/23 inhibitor, in patients with active moderate to severe Crohn's disease. Inflamm Bowel Dis. 2006 Jul;12(7):558-65. PubMed PMID: 16804392.
14: Borchardt JK. Focus on small molecule inhibitors for treatment of inflammatory and autoimmune diseases. Drug News Perspect. 2004 Nov;17(9):607-14. PubMed PMID: 15645018.
Related CAS#
870087-36-8 (mesylate);
541550-19-0 (free base)
