4083. Fingolimod

Nomenclature

CAS number: 162359-55-9
2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol.
C19H33NO2; mol wt 307.47.
C 74.22%, H 10.82%, N 4.56%, O 10.41%.

Description and references

Immunomodulator evoking a reversible redistribution of lymphocytes from the circulation to secondary lymphatic tissue; synthetic analog of myriocin (ISP-1), a fungal metabolite used in traditional Chinese herbal medicine. Prepn: T. Fujita et al., WO 9408943; eidem, US 5604229 (1994, 1997 both to Yoshitomi); K. Adachi et al., Bioorg. Med. Chem. Lett. 5, 853 (1995); M. Kiuchi et al., J. Med. Chem. 43, 2946 (2000). Efficient synthesis: P. Durand et al., Synthesis 2000, 505. Clinical pharmacokinetics: B. D. Kahan et al., Transplantation 76, 1079 (2003). Clinical evaluation in renal transplant: H. Tedesco-Silva et al., ibid. 77, 1826 (2004). Review of immunopharmacology: P. Troncoso, B. D. Kahan, Clin. Biochem. 31, 369-373 (1998); of mechanism of action: V. Brinkmann, K. R. Lynch, Curr. Opin. Immunol. 14, 569-575 (2002); and pharmacology: T. T. Aki, B. D. Kahan, Expert Opin. Biol. Ther. 3, 665-681 (2003); of development and therapeutic potential: F. J. Dumont, IDrugs 8, 236-253 (2005).

Chemical structure

Properties

Crystals from ethyl acetate, mp 103-105°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 162359-56-0
FTY-720.
C19H33NO2.HCl; mol wt 343.93.
C 66.35%, H 9.96%, N 4.07%, O 9.30%, Cl 10.31%.

Properties

Crystals from ethanol, mp 118-120°. Also reported as white solid from ethyl alcohol + ethyl acetate, mp 107-108° (Kiuchi). Sol in water, ethanol. LD50 orally in rats: 300-600 mg/kg (Troncoso).

Therapeutic Category

Immunosuppressant.

Keywords

Immunosuppressant