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Compound Detail

CHEMBL2103873

MACITENTAN
💊 Approved Drug
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💊 Approved Drug
CCCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1-c1ccc(Br)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2103873
Name MACITENTAN
Phase Approved
Structure Type MOL
InChI Key JGCMEBMXRHSZKX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

ACT 064992 ACT-064992 Macitentan Macitentan component of opsynvi Opsumit
5
Targets
10
Activities
2
Assay Types
14
PK Parameters
20
Publications
5
Known Names
11
Indications
1
Mechanisms

Molecular Properties

588.3
MW (Da)
3.57
ALogP
8
HBA
2
HBD
128.2
PSA (Ų)
0.33
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -entan
USAN Year 2011

Extended Properties

Molecular Formula C19H20Br2N6O4S
MW 588.28
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.23

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Endothelin receptor, ET-A/ET-B antagonist ANTAGONIST Endothelin receptor, ET-A/ET-B ✓ ✓

Indications

Familial Primary Pulmonary Hypertension Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Hernias, Diaphragmatic, Congenital Pulmonary Embolism Scleroderma, Systemic Ulcer Heart Failure Idiopathic Pulmonary Fibrosis Glioblastoma

ATC Classification

C02KX04
macitentan
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 7 meas. best 9.3
Ki 3 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Endothelin-1 receptor
CHEMBL252
 IC50 9.3 9.0233 0.5 3
Endothelin receptor type B
CHEMBL1785
 IC50 6.41 6.2767 391.0 3
D(3) dopamine receptor
CHEMBL234
 Ki 6.0 6.0 1004.5 1
Translocator protein
CHEMBL5742
 Ki 5.67 5.67 2118.4 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.32 5.32 4831.1 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 27500.0 ng.hr.mL-1 Canis lupus familiaris
AUC 3170.0 ng.hr.mL-1 Canis lupus familiaris
AUC 18500.0 ng.hr.mL-1 Rattus norvegicus
AUC 2680.0 ng.hr.mL-1 Rattus norvegicus
CL 5.4 mL.min-1.kg-1 Canis lupus familiaris
CL 6.7 mL.min-1.kg-1 Rattus norvegicus
Cmax 7802.41 nM Canis lupus familiaris
Cmax 2838.78 nM Rattus norvegicus
F 87.0 % Canis lupus familiaris
F 69.0 % Rattus norvegicus
T1/2 4.1 hr Canis lupus familiaris
T1/2 5.1 hr Rattus norvegicus
Tmax 2.0 hr Canis lupus familiaris
Tmax 6.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Endothelin-1 receptor IC50 = 0.5 nM 9.3 Displacement of [I125]ET1 from recombinant ETA receptor expressed in CHO cells a... 22862294
Endothelin-1 receptor IC50 = 0.5 nM 9.3 Displacement of [125I]-ET-1 from human ETA receptor expressed in CHO cell membra... 27321813
Endothelin-1 receptor IC50 = 3.4 nM 8.47 Antagonist activity at human ETA receptor expressed in CHO cells in presence of ... 27321813
Endothelin receptor type B IC50 = 391.0 nM 6.41 Displacement of [I125]ET1 from recombinant ETB receptor expressed in CHO cells a... 22862294
Endothelin receptor type B IC50 = 391.0 nM 6.41 Displacement of [125I]-ET-1 from human ETB receptor expressed in CHO cell membra... 27321813
Endothelin receptor type B IC50 = 987.0 nM 6.01 Antagonist activity at human ETB receptor expressed in CHO cells in presence of ... 27321813
D(3) dopamine receptor Ki = 1004.5 nM 6.0 PDSP Secondary Binding target: DRD3 - Compounds are tested at 10 uM concentratio... -
Translocator protein Ki = 2118.36 nM 5.67 PDSP Secondary Binding target: TSPO - Compounds are tested at 10 uM concentratio... -
Sodium-dependent noradrenaline transporter Ki = 4831.14 nM 5.32 PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724696 U2OS 24
- 10.6019/CHEMBL5724696 TERT-RPE1 24
22862294 10.1021/jm3009103 Rattus norvegicus 17
- 10.6019/CHEMBL4689842 HEK-293T 10
22862294 10.1021/jm3009103 Canis familiaris 9
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL4689842 Fibroblast 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
27321813 10.1016/j.bmcl.2016.06.014 Endothelin receptor type B 2
27321813 10.1016/j.bmcl.2016.06.014 Endothelin-1 receptor 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2

Data from ChEMBL 36 via Core Engine