Amiselimod HCl (formerly also known as MT-1303) is a novel, potent and selective immunosuppressant and sphingosine 1 phosphate receptor (S1P1) modulator. Amiselimod may be helpful in the treatment of psoriasis, inflammatory bowel disorders, autoimmune diseases, inflammatory diseases, and multiple sclerosis. Mitsubishi Tanabe Pharma Corporation is now working on amiselimod to lessen the bradycardia effects of fingolimod and other S1P receptor modulators.
Physicochemical Properties
| Molecular Formula | C19H31CLF3NO3 |
| Molecular Weight | 413.910 |
| Exact Mass | 413.194 |
| Elemental Analysis | C, 55.14; H, 7.55; Cl, 8.56; F, 13.77; N, 3.38; O, 11.60 |
| CAS # | 942398-84-7 |
| Related CAS # | 942398-84-7 (HCl); 942399-20-4 |
| PubChem CID | 67418070 |
| Appearance | White to off-white solid powder |
| LogP | 0 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 27 |
| Complexity | 376 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | Cl.FC(C1C(OCCCCCCC)=CC=C(CCC(CO)(CO)N)C=1)(F)F |
| InChi Key | GEDVJGOVRLHFQG-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C19H30F3NO3.ClH/c1-2-3-4-5-6-11-26-17-8-7-15(12-16(17)19(20,21)22)9-10-18(23,13-24)14-25;/h7-8,12,24-25H,2-6,9-11,13-14,23H2,1H3;1H |
| Chemical Name | 2-amino-2-[2-[4-heptoxy-3-(trifluoromethyl)phenyl]ethyl]propane-1,3-diol;hydrochloride |
| Synonyms | MT-1303; MT1303; MT 1303; Amiselimod Hydrochloride |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | Amiselimod-P showed potent selectivity for S1P1 and high selectivity for S1P5 receptors, with minimal agonist activity for S1P4 and no distinct agonist activity for S1P2 or S1P3 receptors and approximately five-fold weaker GIRK activation than fingolimod-P. After oral administration of amiselimod or fingolimod at 1 mg·kg-1 , the concentration of amiselimod-P in rat heart tissue was lower than that of fingolimod-P, potentially contributing to the minimal cardiac effects of amiselimod. A telemetry study in monkeys confirmed that amiselimod did not affect heart rate or ECG parameters. |
| References |
[1]. Amiselimod, a novel sphingosine 1-phosphate receptor-1 modulator, has potent therapeutic efficacy for autoimmune diseases, with low bradycardia risk. Br J Pharmacol. 2016 Oct 7. [2]. Safety and efficacy of amiselimod in relapsing multiple sclerosis (MOMENTUM): a randomised, double-blind, placebo-controlled phase 2 trial. Lancet Neurol. 2016 Oct;15(11):1148-59. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~110 mg/mL (~265.8 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (6.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (6.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4160 mL | 12.0799 mL | 24.1598 mL | |
| 5 mM | 0.4832 mL | 2.4160 mL | 4.8320 mL | |
| 10 mM | 0.2416 mL | 1.2080 mL | 2.4160 mL |