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Ponesimod

Product Name
Ponesimod
CAS No.
854107-55-4
Chemical Name
Ponesimod
Synonyms
PonesiMod;CS-2358;CS-2110;ACT 128800;CAS:854107-55-4;PONESIMOD,ACT-128800;Ponesimod, 10 mM in DMSO;ACT128800;ACT 128800;ACT-128800;Ponesimod, sphingosine-1-phophate receptor agonist;(2Z,5Z)-5-(3-CHLORO-4-((R)-2,3-DIHYDROXYPROPOXY)BENZYLIDENE)-2-(PROPYLIMINO)-3-(O-TOLYL)THIAZOLIDIN-
CBNumber
CB22598855
Molecular Formula
C23H25ClN2O4S
Formula Weight
460.97
MOL File
854107-55-4.mol
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Ponesimod Property

Boiling point:
658.0±65.0 °C(Predicted)
Density 
1.30±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
A crystalline solid
pka
13.38±0.20(Predicted)
color 
Off-white to yellow
InChIKey
LPAUOXUZGSBGDU-STDDISTJSA-N
SMILES
S1/C(=C\C2=CC=C(OC[C@H](O)CO)C(Cl)=C2)/C(=O)N(C2=CC=CC=C2C)/C/1=N/CCC
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
22053
Product name
Ponesimod
Purity
≥98%
Packaging
1mg
Price
$38
Updated
2024/03/01
Cayman Chemical
Product number
22053
Product name
Ponesimod
Purity
≥98%
Packaging
5mg
Price
$172
Updated
2024/03/01
Cayman Chemical
Product number
22053
Product name
Ponesimod
Purity
≥98%
Packaging
10mg
Price
$299
Updated
2024/03/01
Cayman Chemical
Product number
22053
Product name
Ponesimod
Purity
≥98%
Packaging
25mg
Price
$586
Updated
2024/03/01
TRC
Product number
P689490
Product name
Ponesimod
Packaging
500μg
Price
$140
Updated
2021/12/16
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Ponesimod Chemical Properties,Usage,Production

Description

Ponesimod is an oral drug developed by Johnson & Johnson's Janssen Pharmaceuticals unit and approved in 2021 for the treatment of relapsing multiple sclerosis (MS). MS is a chronic inflammatory disease that affects the central nervous system, resulting in neurological dysfunction and disability.

Uses

Ponesimod is an orally active sphingosine-1-phosphate receptor agonist. It protects against lymphocyte-mediated tissue inflammation.

brand name

Ponvory

Biological Activity

ec50: 5.7 nmponesimod is a sphingosine-1-phosphate receptor 1 (s1p1) modulator.lymphocyte exit from lymph nodes and its recirculation into blood is reported to be controlled by s1p. the cellular receptor mediating lymphocyte exit is one of five s1p receptors, s1p1. thus, the nonselective agonists for s1p1 lead to blood lymphocyte count reduction.

Mechanism of action

Ponesimod is a selective sphingosine-1-phosphate (S1P) receptor 1 (S1PR1) agonist. S1P is an intracellular signalling molecule involved in a variety of biological processes including cell migration and survival.Ponesimod works by binding to the S1P1 receptor, leading to internalisation of the receptor. thereby inhibiting the efflux of lymphocytes from the lymph nodes. This action reduces the number of lymphocytes in the blood and limits their ability to reach sites of inflammation, helping to slow the progression of multiple sclerosis.

Synthesis

Ponesimod was synthesised using a three-component coupling of isothiocyanate 16.1, n-propylamine and 2-bromoacetylbromide 16.2 to construct the thiazolidin-4-one parent nucleus 16.3.The regioselectivity of this cyclisation was heavily dependent on the haloacetic acid derivative chosen; in this case, 2-bromoacetylbromide 16.2 showed a high regioselectivity for the desired 16.3 (ratio 41:1, 16.3: 16.4) showed high regioselectivity, in contrast to the lower selectivity of methyl 2-bromoacetate (ratio 1:10, 16.3:16.4). Subsequent hydroxyaldol condensation (aldol-type condensation) with aldehyde 16.5 yielded phenol 16.6, and overall high yields were obtained from the starting isothiocyanate 16.1. The final step involved the attachment of chiral chloropropanediol 16.7 to phenol 16.6 via the SN2 mechanism in the presence of a base, resulting in the synthesis of Ponesimod (16).

in vitro

previous study found that ponesimod could activate s1p1-mediated signal transduction with high potency. moreover, relative to the potency for s1p, the potency of ponesimod at human recombinant receptors was 4.4-fold higher for s1p1 and 150-fold lower for human s1p3. thus, ponesimod was 650-fold more selective for human s1p1 over s1p3 than the endogeneous ligand [1].

in vivo

animal study showed that the oral administration of ponesimod to rats resulted in a dose-dependent decrease of blood lymphocyte count, and the blood lymphocyte count returned to baseline within 48 h after discontinuation of ponesimod treatment. in addition, ponesimod prevented inflammatory cell accumulation, edema formation, as well as cytokine release in the skin of mice with delayed-type hypersensitivity. furthermore, in rats with adjuvant-induced arthritis, ponesimod could also prevent the increase in paw volume and joint inflammation [2].

IC 50

S1PR1: 6 nM (IC50); S1PR5: 142 nM (IC50); S1PR4: 1956 nM (IC50); S1PR3: 2068 nM (IC50)

References

[1] piali l, froidevaux s, hess p, nayler o, bolli mh, schlosser e, kohl c, steiner b, clozel m. the selective sphingosine 1-phosphate receptor 1 agonist ponesimod protects against lymphocyte-mediated tissue inflammation. j pharmacol exp ther. 2011 may;337(2):547-56.
[2] d'ambrosio d, freedman ms, prinz j. ponesimod, a selective s1p1 receptor modulator: a potential treatment for multiple sclerosis and other immune-mediated diseases. ther adv chronic dis. 2016 jan;7(1):18-33.

Ponesimod Preparation Products And Raw materials

Raw materials

Preparation Products

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Ponesimod Suppliers

China 108 India 1 United States 12 Global 121
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
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60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354; +17819995354
Email
marketing@targetmol.com
Country
United States
ProdList
32435
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
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58
Cckinase, Inc.
Tel
+1 (732)236-3202
Email
sales@cckinase.com
Country
United States
ProdList
2738
Advantage
58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63687
Advantage
58
Aladdin Scientific
Tel
Email
tp@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354;
Email
support@targetmol.com
Country
United States
ProdList
39035
Advantage
58
ApexBio Technology
Tel
--
Fax
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Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
Abcam Limited
Tel
--
Fax
--
Email
us.orders@abcam.com
Country
United States
ProdList
6001
Advantage
50
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
International Laboratory Limited
Tel
--
Fax
--
Email
admin@intlab.org
Country
United States
ProdList
5356
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50
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View Lastest Price from Ponesimod manufacturers

Wuhan Nutra Biotechnology Co.,Ltd
Product
Ponesimod 854107-55-4
Price
US $1000.00-0.00/g
Min. Order
1g
Purity
98%+
Supply Ability
100kgs
Release date
2021-05-19
Career Henan Chemical Co
Product
PONESIMOD 854107-55-4
Price
US $1.00/KG
Min. Order
1KG
Purity
97%-99.9%
Supply Ability
100kg
Release date
2019-12-26

854107-55-4, PonesimodRelated Search:


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