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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
Molecular Formula C21H21FN2O4S
Molecular Weight 416.466
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
1,040

Originator

Bayer
150

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Thromboxane A2 receptor
20
Antagonist
2,849
 10.0 nM [Ki]
G protein-coupled receptor 44
7
Antagonist
2,849
 30.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Allergic rhinitis
104
 Primary
Approved
8,583
BAYNAS

Cmax

ValueDoseCo-administeredAnalytePopulation
85 ng/mL
5 mg single, oral
 RAMATROBAN plasma
Homo sapiens
126.9 ng/mL
10 mg single, oral
 RAMATROBAN plasma
Homo sapiens
349.6 ng/mL
20 mg single, oral
 RAMATROBAN plasma
Homo sapiens
103.7 ng/mL
25 mg single, oral
 RAMATROBAN plasma
Homo sapiens
211.1 ng/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
237.2 ng/mL
100 mg single, oral
 RAMATROBAN plasma
Homo sapiens
689.1 ng/mL
150 mg single, oral
 RAMATROBAN plasma
Homo sapiens
209 ng/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
265 ng/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
320.9 ng/mL
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
302.5 ng/mL
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
518.1 ng/mL
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
749.8 ng/mL
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
404.5 ng/mL
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
457.9 ng/mL
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
137.4 ng × h/mL
5 mg single, oral
 RAMATROBAN plasma
Homo sapiens
193.6 ng × h/mL
10 mg single, oral
 RAMATROBAN plasma
Homo sapiens
555.2 ng × h/mL
20 mg single, oral
 RAMATROBAN plasma
Homo sapiens
422.9 ng × h/mL
25 mg single, oral
 RAMATROBAN plasma
Homo sapiens
972.8 ng × h/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
1284.9 ng × h/mL
100 mg single, oral
 RAMATROBAN plasma
Homo sapiens
3214.8 ng × h/mL
150 mg single, oral
 RAMATROBAN plasma
Homo sapiens
996.6 ng × h/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
884.8 ng × h/mL
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
1139.1 ng × h/mL
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
1142.2 ng × h/mL
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
1703.1 ng × h/mL
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2099.4 ng × h/mL
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
1188 ng × h/mL
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
1220.3 ng × h/mL
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.93 h
5 mg single, oral
 RAMATROBAN plasma
Homo sapiens
1.79 h
10 mg single, oral
 RAMATROBAN plasma
Homo sapiens
1.95 h
20 mg single, oral
 RAMATROBAN plasma
Homo sapiens
2.21 h
25 mg single, oral
 RAMATROBAN plasma
Homo sapiens
2.03 h
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
2.33 h
100 mg single, oral
 RAMATROBAN plasma
Homo sapiens
4.45 h
150 mg single, oral
 RAMATROBAN plasma
Homo sapiens
2.17 h
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
1.52 h
50 mg single, oral
 RAMATROBAN plasma
Homo sapiens
2.63 h
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2.13 h
75 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2.54 h
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2.31 h
100 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2.34 h
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens
2.93 h
50 mg 2 times / day multiple, oral
 RAMATROBAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1.95%
RAMATROBAN plasma
Homo sapiens

Doses

PubMed

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.
Substance Class Chemical
Record UNII
P1ALI72U6C
Record Status Validated (UNII)
Record Version
NIH
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