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R0531

Sigma-Aldrich

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
MDL number:
MFCD00887606
UNSPSC Code:
51111800
PubChem Substance ID:
329823986
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ≥40 mg/mL
H2O: insoluble

originator

Bayer

storage temp.

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

InChI key

LDXDSHIEDAPSSA-OAHLLOKOSA-N

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. 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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Update on the development of antagonists of chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2). From lead optimization to clinical proof-of-concept in asthma and allergic rhinitis.
Roy Pettipher et al.
Journal of medicinal chemistry, 55(7), 2915-2931 (2012-01-10)
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
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
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
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
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