(S) FTY720 Phosphate

Names

[ Name ]:
(S) FTY720 Phosphate

[Synonym ]:
1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-, mono(dihydrogen phosphate) (ester), (2S)-
(S)-2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol mono(dihydrogenphosphate) ester
(2S)-2-Amino-2-(hydroxymethyl)-4-(4-octylphenyl)butyl dihydrogen phosphate
FTY720 (S)-Phosphate
fingolimod-P
1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-, mono(dihydrogen phosphate) (ester)
(S)-FTY720-P
2-Amino-2-(hydroxymethyl)-4-(4-octylphenyl)butyl dihydrogen phosphate
2-(S)-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol Mono(dihydrogen phosphate) Ester
(S)-FTY720
2-ammonio-2-(hydroxymethyl)-4-(4-octylphenyl)butyl hydrogen phosphate
(S)-FTY720-phosphate
[14C]-(S)-FTY720P

Biological Activity

[Description]:

FTY720 (S)-Phosphate is an agonist of S1P receptor 1 (S1PR1), used in the research of acute inflammatory diseases such as acute lung injury.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> LPL Receptor

Research Areas >> Inflammation/Immunology

[Target]

S1PR1[1]

[In Vitro]

FTY720 (S)-Phosphate is an agonist of S1PR1. FTY720 (S)-Phosphate (Tys, 1 µM) maintains S1PR1 protein expression, enhances the human pulmonary artery endothelial cells barrier via S1PR1, but shows no effect on inducing ubiquitination of S1PR1. FTY720 (S)-Phosphate (0.01-50 µM) also reduces β-arrestin recruitment to S1PR1[1].

[In Vivo]

FTY720 (S)-Phosphate (0.5 mg/kg, i.p.) preserves S1PR1 expression in mouse lungs, is protective in bleomycin-induced acute lung injury (ALI) and attenuates lung tissue leukocyte infiltration in bleomycin-injured mice[1].

[Animal admin]

Mice[1]Male C57BL/6 (20-25 g) mice 8-10 weeks old receive a single intratracheal dose of bleomycin at 0.6 U/kg (or sterile saline) on Day 0 followed immediately by intraperitoneal injection of FTY720 (S)-Phosphate (0.5 mg/kg), FTY720 (0.5 mg/kg), or saline. Additional doses of FTY720 (S)-Phosphate or FTY720 are injected on Days 3 and 6. Bronchoalveolar lavage (BAL) fluid and lungs are then collected on Day 7. BAL fluid is used to detect BAL protein levels, WBC count, and WBC differential count. Lungs are perfused with saline to remove blood for Western blot, tissue albumin, and histopathology evaluation. Peripheral blood is obtained on Day 7 for examination of total cell counts and lymphocytes. Experiments are repeated 3 times. 6-10 mice are used per experimental group[1].

[References]

[1]. Wang L, et al. FTY720 (s)-phosphonate preserves sphingosine 1-phosphate receptor 1 expression and exhibits superior barrier protection to FTY720 in acute lung injury. Crit Care Med. 2014 Mar;42(3):e189-99.

[2]. Lingling Jia, et al. Clostridium butyricum CGMCC0313.1 Protects against Autoimmune Diabetes by Modulating Intestinal Immune Homeostasis and Inducing Pancreatic Regulatory T Cells. Front Immunol. 2017 Oct 19;8:1345.

[Related Small Molecules]

Ki16425 | Siponimod | AM966 | Ozanimod | BMS-986020 | LPA2 antagonist 1 | TY-52156 | AM095 | Etrasimod | ACT-334441 | Ponesimod | Amiselimod hydrochloride | S1p receptor agonist 1 | ONO-7300243

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
584.2±60.0 °C at 760 mmHg

[ Melting Point ]:
184-186ºC

[ Molecular Formula ]:
C₁₉H₃₄NO₅P

[ Molecular Weight ]:
387.451

[ Flash Point ]:
307.1±32.9 °C

[ Exact Mass ]:
387.217468

[ PSA ]:
122.82000

[ LogP ]:
4.27

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.541

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Active, phosphorylated fingolimod inhibits histone deacetylases and facilitates fear extinction memory.

Nat. Neurosci. 17(7) , 971-80, (2014)

FTY720 (fingolimod), an FDA-approved drug for treatment of multiple sclerosis, has beneficial effects in the CNS that are not yet well understood, independent of its effects on immune cell trafficking...

Related Compounds

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