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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
Shandong Jirun Biomedical Technology Co., Ltd.
Tel
0539-0539-8613587 17661611089
Fax
qq2639273505
Email
2639273505@qq.com
Country
China
ProdList
207
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
Beijing HwrkChemical Technology Co., Ltd
Tel
18515581800 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
9400
Advantage
55
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4747
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
AdooQ Bioscience CHINA
Tel
025-58849295 18951903616;
Fax
025-68650336
Email
info@adooq.cn
Country
China
ProdList
2990
Advantage
60
Shanghai Lollane Biological Technology Co.,Ltd.
Tel
021-52996696，15000506266 15000506266
Fax
+86-21-52996696
Country
China
ProdList
4757
Advantage
55
Shanghai eliv pharmaceutical Co.,Ltd.
Tel
021-50158063
Fax
021-6153 1846
Email
sales@elivpharma.com
Country
China
ProdList
477
Advantage
58
Suzhou PengXu PharmaTech Co., Ltd.
Tel
15850786624
Email
sales@cqpharm.com
Country
China
ProdList
88
Advantage
58
Shanghai Shanyuan pharmaceutical technology co., LTD
Tel
021-31761238 13167072949
Fax
021-31761238
Email
3146446224@qq.com
Country
China
ProdList
1379
Advantage
55
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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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