Fingolimod

Title: Fingolimod
CAS Registry Number: 162359-55-9
CAS Name: 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol
Molecular Formula: C19H33NO2
Molecular Weight: 307.47
Percent Composition: C 74.22%, H 10.82%, N 4.56%, O 10.41%
Literature 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, Exp. Opin. Biol. Ther. 3, 665-681 (2003); of development and therapeutic potential: F. J. Dumont, IDrugs 8, 236-253 (2005).
Properties: Crystals from ethyl acetate, mp 103-105°.
Melting point: mp 103-105°
Derivative Type: Hydrochloride
CAS Registry Number: 162359-56-0
Manufacturers' Codes: FTY-720
Molecular Formula: C19H33NO2.HCl
Molecular Weight: 343.93
Percent Composition: 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).
Melting point: mp 118-120°; mp 107-108°
Toxicity data: LD50 orally in rats: 300-600 mg/kg (Troncoso)
Therap-Cat: Immunosuppressant.
Keywords: Immunosuppressant.
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Fingolimod
Fingolimod2DACS.svg
Fingolimod3Dan.gif
Systematic (IUPAC) name
2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol
Clinical data
Trade names Gilenya
AHFS/Drugs.com monograph
Licence data EMA:Link, US FDA:link
Pregnancy cat. D (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Identifiers
CAS number 162359-55-9 N
ATC code L04AA27
PubChem CID 107970
ChemSpider 97087 YesY
UNII 3QN8BYN5QF YesY
ChEBI CHEBI:63115 N
ChEMBL CHEMBL314854 YesY
Chemical data
Formula C19H33NO2 
Mol. mass 307.471 g/mol
 N (what is this?)  (verify)

Fingolimod (INN, trade name Gilenya, Novartis) is an immunomodulating drug, approved for treating multiple sclerosis. It has reduced the rate of relapses in relapsing-remitting multiple sclerosis by over half. Fingolimod is a sphingosine 1-phosphate receptor modulator, which sequesters lymphocytes in lymph nodes, preventing them from contributing to an autoimmune reaction.