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R0531

Sigma-Aldrich

Ramatroban

≥98% (HPLC), solid

Synonym(e):

(+)-(3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic acid, BAY u3405

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About This Item

Empirische Formel (Hill-System):
C21H21FN2O4S
CAS-Nummer:
116649-85-5
Molekulargewicht:
416.47
MDL-Nummer:
MFCD00887606
UNSPSC-Code:
51111800
PubChem Substanz-ID:
329823986
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

solid

Farbe

white

Löslichkeit

DMSO: ≥40 mg/mL
H2O: insoluble

Ersteller

Bayer

Lagertemp.

2-8°C

SMILES String

OC(=O)CCn1c2CC[C@H](Cc2c3ccccc13)NS(=O)(=O)c4ccc(F)cc4

InChI

1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1

InChIKey

LDXDSHIEDAPSSA-OAHLLOKOSA-N

Biochem./physiol. Wirkung

Ramatroban aids in the reduction of myocardial ischemia-reperfusion injury, lipopolysaccharide-induced shock, and vagal neuroeffector transmission in the tracheal smooth muscle of experimental models. In addition, it also suppresses allergen and IgE antibody-mediated skin and nasal reactions and eosinophilia in animal models with asthma.
Ramatroban is used for the treatment of allergic rhinitis as an antagonist of the thromboxane receptor. It is also an antagonist of the DP2 receptor with IC50 values of 100-170 nM. It is more potent at the DP2 receptor than the TP receptor by 4-5 fold. It is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.

Leistungsmerkmale und Vorteile

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Hiromi Sugimoto et al.
European journal of pharmacology, 524(1-3), 30-37 (2005-11-01)
We previously showed that ramatroban (Baynastrade mark), a thromboxane A(2) (TxA(2)) antagonist, had inhibited prostaglandin D(2) (PGD(2))-stimulated human eosinophil migration mediated through activation of chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2). However, detailed pharmacological characterization of its inhibitory activity
Toshiaki Ishizuka et al.
Cardiovascular drug reviews, 22(2), 71-90 (2004-06-05)
It is known that thromboxane A2 (TXA2) contributes to various diseases such as bronchial asthma, ischemic heart disease, cerebrovascular disorders and allergic rhinitis. A number of TXA2 synthase inhibitors and TXA2 receptor (TP receptor) antagonists have been developed to treat
Stéphanie Rolin et al.
European journal of pharmacology, 533(1-3), 89-100 (2006-02-07)
COPD (Chronic Obstructive Pulmonary Disease) and bronchial asthma are two severe lung diseases which represent a major problem of world public health. Leukotrienes and prostanoids play an important role in the pathogenesis of pulmonary diseases. Prostanoids: prostaglandins (PGs) and thromboxane
Petra Schratl et al.
European journal of immunology, 36(9), 2401-2409 (2006-08-15)
Several chemoattractants can regulate the recruitment of eosinophils to sites of inflammation, but the hierarchy among them is unknown. We observed here that eosinophil chemotaxis towards eotaxin or 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) was amplified up to sixfold in the presence of
Eduardo Busto et al.
The Journal of organic chemistry, 77(10), 4842-4848 (2012-04-21)
A chemoenzymatic asymmetric route for the preparation of enantiopure (R)-ramatroban has been developed for the first time. The action of lipases and oxidoreductases has been independently studied, and both were found as excellent biocatalysts for the production of adequate chiral
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