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 20 Target ID: CHEMBL2069 Sources: http://www.nippon-shinyaku.co.jp/assets/files/pdfs/medicine/product/ha/baynas/interview_baynas_t.pdf	Antagonist 2849		10.0 nM [Ki]
G protein-coupled receptor 44 7 Target ID: CHEMBL5071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179446	Antagonist 2849		30.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 104 Sources: http://www.nippon-shinyaku.co.jp/assets/files/pdfs/medicine/product/ha/baynas/interview_baynas_t.pdf	Primary		Approved 8583	BAYNAS Approved Use Treatment of Allergic rhinitis. Launch Date 2000

C_max

Value	Dose	Analyte	Population
85 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
126.9 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
349.6 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
103.7 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
211.1 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
237.2 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
689.1 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
209 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
265 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
320.9 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
302.5 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
518.1 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
749.8 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
404.5 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
457.9 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
137.4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
193.6 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
555.2 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
422.9 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
972.8 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1284.9 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3214.8 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
996.6 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
884.8 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1139.1 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1142.2 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1703.1 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2099.4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1188 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1220.3 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
1.93 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.79 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.95 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=146	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.21 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.03 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.33 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.45 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=148	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.17 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.52 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=30 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=149	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.63 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.13 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=31 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.54 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.31 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=150	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.34 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.93 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=32 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=160	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	RAMATROBAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.95% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/630004_4490021F1025_3_001_1F.pdf#page=34 \| https://www.pmda.go.jp/drugs/2000/g000302/index.html#page=136			RAMATROBAN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
75 mg 2 times / day multiple, oral Studied dose Dose: 75 mg, 2 times / day Route: oral Route: multiple Dose: 75 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8620702/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8620702/	Sources: https://pubmed.ncbi.nlm.nih.gov/8620702/

PubMed

Title	Date	PubMed
Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.	2011-10-27	21916510
Zwitterionic CRTh2 antagonists.	2011-03-24	21355602
Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats.	2006-11	16979129
CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses.	2005-11-07	16256979
Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.	2005-09-16	16030019
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.	2005-03	15563582
Prostaglandin D2-induced eosinophilic airway inflammation is mediated by CRTH2 receptor.	2005-03	15528449
Participation of chemical mediators in the development of experimental allergic conjunctivitis in rats.	2004-11	15351322
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.	2003-11	12975488
The role of chemical mediators in eosinophil infiltration in allergic rhinitis in mice.	2003-04	12689652
Participation of chemical mediators other than histamine in nasal allergy signs: a study using mice lacking histamine H(1) receptors.	2002-08-09	12167471
Differential effects of prostacyclin and iloprost in the isolated carotid artery of the guinea-pig.	2001-08-24	11525776
Binding characteristics of the new thromboxane A2/prostaglandin H2 receptor antagonist [3H]BAY U 3405 to washed human platelets and platelet membranes.	1992-08-04	1387312

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 `Wed Apr 02 09:35:53 GMT 2025` Edited by `admin` on `Wed Apr 02 09:35:53 GMT 2025`
Record UNII	P1ALI72U6C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BAYNAS

Preferred Name

English

RAMATROBAN

Official Name

English

RAMATROBAN [JAN]

Common Name

English

EN-137774

Code

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