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Merck
CN

R0531

Ramatroban

≥98% (HPLC), solid

Synonym(s):

(+)-(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

Empirical Formula (Hill Notation):
C21H21FN2O4S
CAS Number:
116649-85-5
Molecular Weight:
416.47
NACRES:
NA.77
PubChem Substance ID:
329823986
UNSPSC Code:
51111800
MDL number:
MFCD00887606

Key Documents

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Product Name

Ramatroban, ≥98% (HPLC), solid

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

SMILES string

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

InChI key

LDXDSHIEDAPSSA-OAHLLOKOSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ≥40 mg/mL
H2O: insoluble

originator

Bayer

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

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.
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.

Features and Benefits

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000136711
0000136712
049K4719
0000136712
0000136711

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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
Tetsuro Wada et al.
Auris, nasus, larynx, 33(4), 455-460 (2006-08-11)
The pathogenesis of eosinophilic otitis media is not yet fully understood. The purpose of this paper is to describe the clinical course of our two patients with eosinophilic otitis media and to discuss the pathogenesis and treatment of this intractable
J F Royer et al.
European journal of clinical investigation, 38(9), 663-671 (2008-10-08)
Chemoattractant receptor homologous molecule of Th2 cells (CRTH2) has been shown to mediate the chemotaxis of eosinophils, basophils and Th2-type T lymphocytes. The major mast cell product prostaglandin (PG) D(2) is considered to be the principal ligand of CRTH2. We
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
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