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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 of RAMATROBAN

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

Description

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

CNS Non-penetrant
1014
Curator's Comment: Ramatroban and its labeled metabolites did hardly penetrate the blood-brain barrier.

Originator

Bayer
156
Curator's Comment: # Bayer

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 10.0 nM [Ki]
Antagonist
2778
 30.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
BAYNAS

Approved Use

Treatment of Allergic rhinitis.

Launch Date

9.5264637E11
PubMed

PubMed

TitleDatePubMed
Participation of chemical mediators in the development of experimental allergic conjunctivitis in rats.
2004 Nov
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.
2005 Mar
Prostaglandin D2-induced eosinophilic airway inflammation is mediated by CRTH2 receptor.
2005 Mar
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
Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.
2005 Sep 16
Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats.
2006 Nov
Zwitterionic CRTh2 antagonists.
2011 Mar 24
Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.
2011 Oct 27
Patents

Patents

JP2004002353A
2

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.
Name Type Language
RAMATROBAN
INN   JAN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
Code System Code Type Description
INN
7273
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
EVMPD
SUB10245MIG
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
MESH
C063119
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
FDA UNII
P1ALI72U6C
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
WIKIPEDIA
Ramatroban
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
DRUG BANK
DB13036
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL361812
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
DRUG CENTRAL
2354
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
MERCK INDEX
m9488
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID1046685
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
NCI_THESAURUS
C76400
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
SMS_ID
100000080311
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
CAS
116649-85-5
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
PUBCHEM
123879
Created by admin on Sat Dec 16 17:49:57 UTC 2023 , Edited by admin on Sat Dec 16 17:49:57 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of RAMATROBAN
SALT/SOLVATE (PARENT)
Structure of RAMATROBAN SODIUM
NIH
NCATS
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