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SML3668

Sigma-Aldrich

Ceralifimod hydrochloride

≥95% (HPLC)

Synonym(s):

1-((6-(2-Methoxy-4-propylbenzyloxy)-1-methyl-3,4-dihydronaphthalen-2-yl)methyl)azetidine-3-carboxylic acid hydrochloride, 1-[[3,4-Dihydro-6-[(2-methoxy-4-propylphenyl)methoxy]-1-methyl-2-naphthalenyl]methyl]-3-azetidinecarboxylic acid hydrochloride, 1-[[6-[(2-Methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalenyl]methyl]azetidine-3-carboxylic acid hydrochloride, ONO-4641 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H33NO4 · xHCl
Molecular Weight:
435.56 (free base basis)
MDL number:
MFCD28502037
UNSPSC Code:
12352200
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

100

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

N4(CC(C4)C(=O)O)CC1=C(c2c(cc(cc2)OCc3c(cc(cc3)CCC)OC)CC1)C

InChI

1S/C27H33NO4/c1-4-5-19-6-7-22(26(12-19)31-3)17-32-24-10-11-25-18(2)21(9-8-20(25)13-24)14-28-15-23(16-28)27(29)30/h6-7,10-13,23H,4-5,8-9,14-17H2,1-3H3,(H,29,30)

InChI key

QDDQIPUKAXBMBX-UHFFFAOYSA-N

Biochem/physiol Actions

Ceralifimod (ONO-4641) is an orally active, potent, S1P1 & S1P5 subtype-selective sphingosine-1-phosphate (S1P) receptor agonist (rat S1P1 Ki = 0.772 nM, human S1P5/1/4 Ki = 0.574/0.626/28.2 nM, hS1P2/3 Ki >5.45 μM against S1P by binding assays) that suppresses forskolin-stimulated cAMP accumulation (IC50 = 27.3 pM/hS1P1, 28.64 pM/rS1P1, 334 pM/hS1P5 using respective transfectants) and induces S1P1 downregulation with a higher potency than SEW2871 & S1P (EC50 = 0.778, 118, 132 nM, respectively). Ceralifimod decreases peripheral blood lymphocytes (EDmax 100 μg/kg po.) in rats, and shows in vivo efficacy in rat and murine EAE models (30 & 100 μg/kg/day po.).
Orally active, potent, S1P1 & S1P5 subtype-selective sphingosine-1-phosphate (S1P) receptor agonist with in vivo efficacy in rat and murine EAE models.

Caution

Hygroscopic

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Takanori Asakura et al.
Mucosal immunology, 11(6), 1606-1620 (2018-08-18)
Sphingolipids play a pivotal role in the pathogenesis of chronic obstructive pulmonary disease (COPD). However, little is known about the precise roles of sphingosine-1-phosphate (S1P), a bioactive sphingolipid metabolite, and its receptor modulation in COPD. In this study, we demonstrated
Haruto Kurata et al.
Journal of medicinal chemistry, 60(23), 9508-9530 (2017-11-10)
The discovery of 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid 13n (ceralifimod, ONO-4641), a sphingosine-1-phosphate (S1P) receptor agonist selective for S1P1 and S1P5, is described. While it has been revealed that the modulation of the S1P1 receptor is an effective way to treat autoimmune diseases
Quality not quantity for transglutaminase antibody 2: the performance of an endomysial and tissue transglutaminase test in screening coeliac disease remains stable over time
Clinical and Experimental Immunology, 171(1), 100-106 (2013)

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