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Compound Detail

CHEMBL361812

RAMATROBAN
💊 Approved Drug
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💊 Approved Drug
O=C(O)CCn1c2c(c3ccccc31)C[C@H](NS(=O)(=O)c1ccc(F)cc1)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL361812
Name RAMATROBAN
Phase Approved
Structure Type MOL
InChI Key LDXDSHIEDAPSSA-OAHLLOKOSA-N

Known Names

BAY-U-3405 Baynas EN-137774 Ramatroban
8
Targets
30
Activities
3
Assay Types
3
PK Parameters
20
Publications
4
Known Names
2
Indications
2
Mechanisms

Molecular Properties

416.5
MW (Da)
3.09
ALogP
4
HBA
2
HBD
88.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -troban

Extended Properties

Molecular Formula C21H21FN2O4S
MW 416.47
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.31

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
G protein-coupled receptor 44 antagonist ANTAGONIST Prostaglandin D2 receptor 2 ✓ ✓
Thromboxane A2 receptor antagonist ANTAGONIST Thromboxane A2 receptor ✓ ✓

Indications

Asthma Severe Acute Respiratory Syndrome

Activity Summary

IC50 19 meas. best 8.08
Ki 10 meas. best 9.24
Kd 1 meas. best 7.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thromboxane A2 receptor
CHEMBL2069
 Ki 9.24 8.4467 0.6 3
Prostaglandin D2 receptor 2
CHEMBL5071
 Ki 8.37 6.9867 4.3 6
Thromboxane A2 receptor
CHEMBL2069
 IC50 8.08 7.9833 8.4 3
Oryctolagus cuniculus
CHEMBL374
 Kd 7.9 7.9 12.6 1
Prostaglandin D2 receptor 2
CHEMBL5071
 IC50 7.68 6.901 21.0 10
Homo sapiens
CHEMBL372
 IC50 7.3 6.86 50.0 2
Blood
CHEMBL613416
 IC50 5.92 5.92 1210.0 1
Prostaglandin D2 receptor
CHEMBL4427
 Ki 4.96 4.96 11020.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.82 4.82 15000.0 1
Prostaglandin D2 receptor
CHEMBL4427
 IC50 4.48 4.48 33400.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.21 4.21 62400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.81 uL.min-1.(10^6cells)-1 Homo sapiens
CL 6.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thromboxane A2 receptor Ki = 0.58 nM 9.24 Binding affinity to thromboxane receptor 21106375
Prostaglandin D2 receptor 2 Ki = 4.3 nM 8.37 Inhibition of [3H]PGD-2 binding to human chemoattractant receptor-homologous mol... 15715457
Thromboxane A2 receptor Ki = 4.5 nM 8.35 Inhibition of [3H]SQ-29,548 binding to human Thromboxane A2 receptor 15715457
Thromboxane A2 receptor IC50 = 8.4 nM 8.08 Inhibition of beta-arrestin translocation at human Thromboxane A2 receptor in BR... 15715457
Thromboxane A2 receptor IC50 = 9.6 nM 8.02 Inhibition of U-46,619-induced inositol phosphate accumulation at human Thrombox... 15715457
Oryctolagus cuniculus Kd = 12.59 nM 7.9 Compound was tested for inhibition of U-46,619 induced contraction of isolated r... 9871769
Thromboxane A2 receptor IC50 = 14.0 nM 7.85 Displacement of [3H]SQ-29548 from thromboxane receptor in human platelet membran... 19608418
Thromboxane A2 receptor Ki = 18.0 nM 7.75 Inhibitory activity for binding of PGD-2 in hTP binding assay using HEK293 cell ... 15745833
Prostaglandin D2 receptor 2 IC50 = 21.0 nM 7.68 Antagonist activity against CRTh2 receptor in human eosinophils assessed as cell... 19592244
Prostaglandin D2 receptor 2 IC50 = 28.0 nM 7.55 Inhibition of beta-arrestin translocation at human chemoattractant receptor-homo... 15715457
Prostaglandin D2 receptor 2 IC50 = 29.0 nM 7.54 Inhibition of PGD2-induced inositol phosphate formation at human chemoattractant... 15715457
Homo sapiens IC50 = 50.0 nM 7.3 Anti-platelet activity was measured by studying their antagonist effects on huma... 12182849
Prostaglandin D2 receptor 2 Ki = 73.0 nM 7.14 Displacement of [3H]PGD2 from human CRTh2 receptor expressed in CHO cells 19592244
Prostaglandin D2 receptor 2 IC50 = 77.0 nM 7.11 Displacement of [3H]PGD2 from human CRTh2 receptor expressed in HEK293 cells aft... 21355602
Prostaglandin D2 receptor 2 Ki = 137.0 nM 6.86 Binding affinity to human recombinant CRTH2 receptor by cell based radioligand e... 21106375
Prostaglandin D2 receptor 2 IC50 = 169.0 nM 6.77 Antagonist activity at human CRTH2 receptor assessed as inhibition of DK-PGD2-in... 18318469
Prostaglandin D2 receptor 2 IC50 = 195.0 nM 6.71 Antagonist activity against CRTh2 receptor in human whole blood assessed as eosi... 19592244
Prostaglandin D2 receptor 2 IC50 = 210.0 nM 6.68 Antagonist activity against human CRTh2 receptor expressed in CHO cells assessed... 19592244
Prostaglandin D2 receptor 2 Ki = 290.0 nM 6.54 Inhibitory activity for PGD2-mediated receptor activation in a fluorescence assa... 15745833
Prostaglandin D2 receptor 2 Ki = 290.0 nM 6.54 Inhibitory activity for binding of PGD-2 to CRTH-2 in hCRTH-2 binding assay usin... 15745833

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 U2OS 6
- 10.6019/CHEMBL5303304 Fibroblast 6
- 10.6019/CHEMBL3301361 ADMET 6
19592244 10.1016/j.bmcl.2009.06.042 Prostaglandin D2 receptor 2 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL5058564 HEK-293T 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
21355602 10.1021/jm1014549 Prostaglandin D2 receptor 2 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
21601448 10.1016/j.bmcl.2011.04.133 No relevant target 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
15715457 10.1021/jm049036i Thromboxane A2 receptor 3
15715457 10.1021/jm049036i Prostaglandin D2 receptor 2 3
15745833 10.1016/j.bmcl.2004.12.055 Prostaglandin D2 receptor 2 3
- 10.6019/CHEMBL5058564 Fibroblast 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3

Data from ChEMBL 36 via Core Engine