RAMATROBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21FN2O4S
Molecular Weight	416.466
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCN1C2=C(C[C@@H](CC2)NS(=O)(=O)C3=CC=C(F)C=C3)C4=C1C=CC=C4

InChI

InChIKey=LDXDSHIEDAPSSA-OAHLLOKOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H21FN2O4S
Molecular Weight	416.466
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179446 | http://www.nippon-shinyaku.co.jp/assets/files/pdfs/medicine/product/ha/baynas/interview_baynas_t.pdf

Ramatroban is a dual antagonist of thromboxane A2 receptor and PGD2 receptor. The drug was developed by Bayer and tested for the treatment of asthma and allergic rhinitis. In Japan ramatroban reached final approval and is being marketed under the name Baynas. In vitro studies have shown that the drug effectively inhibits smooth muscle cells contraction.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thromboxane A2 receptor 19 Target ID: CHEMBL2069 Sources: http://www.nippon-shinyaku.co.jp/assets/files/pdfs/medicine/product/ha/baynas/interview_baynas_t.pdf	Antagonist 2778		10.0 nM [Ki]
G protein-coupled receptor 44 7 Target ID: CHEMBL5071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179446	Antagonist 2778		30.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: http://www.nippon-shinyaku.co.jp/assets/files/pdfs/medicine/product/ha/baynas/interview_baynas_t.pdf	Primary		Approved 8429	BAYNAS Approved Use Treatment of Allergic rhinitis. Launch Date 2000

PubMed

Title	Date	PubMed
Binding characteristics of the new thromboxane A2/prostaglandin H2 receptor antagonist [3H]BAY U 3405 to washed human platelets and platelet membranes.	1992 Aug 4	1387312
The role of chemical mediators in eosinophil infiltration in allergic rhinitis in mice.	2003 Apr	12689652
Chemoattractant receptor-homologous molecule expressed on Th2 cells activation in vivo increases blood leukocyte counts and its blockade abrogates 13,14-dihydro-15-keto-prostaglandin D2-induced eosinophilia in rats.	2003 Nov	12975488
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.	2005 Mar	15563582
Prostaglandin D2-induced eosinophilic airway inflammation is mediated by CRTH2 receptor.	2005 Mar	15528449
CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses.	2005 Nov 7	16256979
Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.	2005 Sep 16	16030019
Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats.	2006 Nov	16979129
Zwitterionic CRTh2 antagonists.	2011 Mar 24	21355602
Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.	2011 Oct 27	21916510

Patents

Sample Use Guides

In Vivo Use Guide

75 mg is administered orally devided in two doses, after breakfast and after dinner (or before going to bed).

Route of Administration: Oral

In Vitro Use Guide

Human airway smooth muscle preparations and lung strips were treated wuth 10(-6), 10(-7) and 10(-8) M of remetroban to inhibit U46619-induced contractions.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:49:56 GMT 2023` Edited by `admin` on `Sat Dec 16 17:49:56 GMT 2023`
Record UNII	P1ALI72U6C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RAMATROBAN

Official Name

English

RAMATROBAN [JAN]

Common Name

English

EN-137774

Code

English

BAYNAS

Brand Name

English

RAMATROBAN [MART.]

Common Name

English

(+)-(3R)-3-(P-FLUOROBENZENESULFONAMIDO)-1,2,3,4-TETRAHYDROCARBAZOLE-9-PROPIONIC ACID

Systematic Name

English

(3R)-3-(((4-FLUOROPHENYL)SULFONYL)AMINO)-1,2,3,4-TETRAHYDRO-9H-CARBAZOLE-9-PROPANOIC ACID

Systematic Name

English

RAMATROBAN [MI]

Common Name

English

9H-CARBAZOLE-9-PROPANOIC ACID, 3-(((4-FLUOROPHENYL)SULFONYL)AMINO)-1,2,3,4-TETRAHYDRO-, (3R)-

Systematic Name

English

ramatroban [INN]

Common Name

English

Ramatroban [WHO-DD]

Common Name

English

BAY-U-3405

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1327