fingolimod

Ligand id: 2407

Name: fingolimod

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 66.48
Molecular weight 307.25
XLogP 6.61
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

References
1. Cohen JA, Chun J. (2011)
Mechanisms of fingolimod's efficacy and adverse effects in multiple sclerosis.
Ann. Neurol.69 (5): 759-77. [PMID:21520239]
2. Demont EH, Bailey JM, Bit RA, Brown JA, Campbell CA, Deeks N, Dowell SJ, Eldred C, Gaskin P, Gray JR et al.. (2016)
Discovery of Tetrahydropyrazolopyridine as Sphingosine 1-Phosphate Receptor 3 (S1P3)-Sparing S1P1 Agonists Active at Low Oral Doses.
J. Med. Chem.59 (3): 1003-20. [PMID:26751273]
3. Forrest M, Sun SY, Hajdu R, Bergstrom J, Card D, Doherty G, Hale J, Keohane C, Meyers C, Milligan J et al.. (2004)
Immune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes.
J. Pharmacol. Exp. Ther.309 (2): 758-68. [PMID:14747617]
4. Hale JJ, Lynch CL, Neway W, Mills SG, Hajdu R, Keohane CA, Rosenbach MJ, Milligan JA, Shei GJ, Parent SA et al.. (2004)
A rational utilization of high-throughput screening affords selective, orally bioavailable 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonists.
J. Med. Chem.47 (27): 6662-5. [PMID:15615513]
5. Horga A, Montalban X. (2008)
FTY720 (fingolimod) for relapsing multiple sclerosis.
Expert Rev Neurother8 (5): 699-714. [PMID:18457527]
6. Koyrakh L, Roman MI, Brinkmann V, Wickman K. (2005)
The heart rate decrease caused by acute FTY720 administration is mediated by the G protein-gated potassium channel I.
Am. J. Transplant.5 (3): 529-36. [PMID:15707407]
7. Mandala S, Hajdu R, Bergstrom J, Quackenbush E, Xie J, Milligan J, Thornton R, Shei GJ, Card D, Keohane C et al.. (2002)
Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists.
Science296 (5566): 346-9. [PMID:11923495]
8. Qin X, Yue Z, Sun B, Yang W, Xie J, Ni E, Feng Y, Mahmood R, Zhang Y, Yue L. (2013)
Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels.
British Journal of Pharmacology168: 1294-1312. [PMID:23145923]
9. Sanna MG, Liao J, Jo E, Alfonso C, Ahn MY, Peterson MS, Webb B, Lefebvre S, Chun J, Gray N et al.. (2004)
Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.
J. Biol. Chem.279 (14): 13839-48. [PMID:14732717]