Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H20FN2O4S.Na |
| Molecular Weight | 438.448 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-]C(=O)CCN1C2=C(C[C@@H](CC2)NS(=O)(=O)C3=CC=C(F)C=C3)C4=C1C=CC=C4
InChI
InChIKey=JRBVAOJTPBHRQQ-XFULWGLBSA-M
InChI=1S/C21H21FN2O4S.Na/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);/q;+1/p-1/t15-;/m1./s1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C21H20FN2O4S |
| Molecular Weight | 415.458 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9296280
Curator's Comment: Ramatroban and its labeled metabolites did hardly penetrate the blood-brain barrier.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2069 |
10.0 nM [Ki] | ||
Target ID: CHEMBL5071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179446 |
30.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BAYNAS Approved UseTreatment of Allergic rhinitis. Launch Date2000 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85 ng/mL |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 | Co-administered | Analyte | Population |
|---|---|---|---|---|
137.4 ng × h/mL |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.93 h |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.95% |
RAMATROBAN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
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 |
|
| Zwitterionic CRTh2 antagonists. | 2011-03-24 |
|
| Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats. | 2006-11 |
|
| 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 |
|
| Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2. | 2005-09-16 |
|
| Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. | 2005-03 |
|
| Prostaglandin D2-induced eosinophilic airway inflammation is mediated by CRTH2 receptor. | 2005-03 |
|
| Participation of chemical mediators in the development of experimental allergic conjunctivitis in rats. | 2004-11 |
|
| 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 |
|
| The role of chemical mediators in eosinophil infiltration in allergic rhinitis in mice. | 2003-04 |
|
| Participation of chemical mediators other than histamine in nasal allergy signs: a study using mice lacking histamine H(1) receptors. | 2002-08-09 |
|
| Differential effects of prostacyclin and iloprost in the isolated carotid artery of the guinea-pig. | 2001-08-24 |
|
| 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 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1839139
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
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admin
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Edited
Mon Mar 31 17:59:17 GMT 2025
by
admin
on
Mon Mar 31 17:59:17 GMT 2025
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| Record UNII |
5J3I129AXS
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| Record Status |
Validated (UNII)
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| Record Version |
|
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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1040405-44-4
Created by
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67027609
Created by
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5J3I129AXS
Created by
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