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Compound Detail

CHEMBL494

ILOPROST
💊 Approved Drug
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💊 Approved Drug
CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O

Basic Information

ChEMBL ID CHEMBL494
Name ILOPROST
Phase Approved
Structure Type MOL
InChI Key HIFJCPQKFCZDDL-ACWOEMLNSA-N
Therapeutic ✓ Yes

Known Names

Aurlumyn Ciloprost Endoprost Ilomedin Iloprost Ventavis ZK 00036374 ZK-00036374 ZK-36374
11
Targets
41
Activities
3
Assay Types
11
PK Parameters
20
Publications
9
Known Names
17
Indications
1
Mechanisms

Molecular Properties

360.5
MW (Da)
3.54
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.35
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2003
Availability Prescription
Chirality Racemic

Routes of Administration

Parenteral Topical

Flags

Natural Product
USAN Stem -prost
USAN Year 2004

Extended Properties

Molecular Formula C22H32O4
MW 360.49
Aromatic Rings 0
Heavy Atoms 26
NP-Likeness 1.99

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Prostanoid IP receptor agonist AGONIST Prostacyclin receptor

Indications

Hypertension, Pulmonary Hypertension, Pulmonary Pulmonary Arterial Hypertension Thrombosis Raynaud Disease Respiratory Distress Syndrome Shock, Septic Heart Arrest Lung Neoplasms Lung Neoplasms Multiple Organ Failure Pulmonary Disease, Chronic Obstructive Renal Insufficiency, Chronic Scleroderma, Systemic Humeral Fractures Myocardial Infarction Asthma

ATC Classification

B01AC11
iloprost
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 25 meas. best 9.7
Ki 9 meas. best 9.0
EC50 7 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Homo sapiens
CHEMBL372
IC50 9.7 8.5445 0.2 11
Prostaglandin E2 receptor EP1 subtype
CHEMBL1811
EC50 9.52 9.52 0.3 1
Prostacyclin receptor
CHEMBL1995
EC50 9.4 9.01 0.4 2
Prostacyclin receptor
CHEMBL3322
EC50 9.16 9.16 0.7 1
Prostacyclin receptor
CHEMBL3322
Ki 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
Ki 8.8 8.785 1.6 2
Unchecked
CHEMBL612545
IC50 8.6 7.15 2.5 2
Cell line
CHEMBL614840
IC50 8.6 8.6 2.5 1
Prostacyclin receptor
CHEMBL1995
Ki 8.49 8.266 3.2 5
Plasma
CHEMBL613652
IC50 8.3 8.3 5.0 2
Prostacyclin receptor
CHEMBL1995
IC50 8.08 7.8663 8.4 8
Rattus norvegicus
CHEMBL376
IC50 7.94 7.94 11.4 1
Prostaglandin D2 receptor
CHEMBL4427
EC50 6.83 6.26 147.0 2
Prostaglandin E2 receptor EP2 subtype
CHEMBL1881
EC50 5.68 5.68 2094.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
Ki 5.43 5.43 3700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 58.0 mL.min-1.kg-1 Macaca
CL 67.0 mL.min-1.kg-1 Canis lupus familiaris
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 17.0 mL.min-1.kg-1 Homo sapiens
CL 32.0 mL.min-1.kg-1 Rattus norvegicus
Fu 0.4 - Homo sapiens
MRT 0.39 hr Homo sapiens
T1/2 0.57 hr Homo sapiens
T1/2 0.3333 hr Homo sapiens
t1/2 - - Homo sapiens
t1/2 - - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Homo sapiens IC50 = 0.2 nM 9.7 Compound was tested for inhibition of blood platelet aggregation induced by ADP;... -
Prostaglandin E2 receptor EP1 subtype EC50 = 0.3 nM 9.52 Agonist activity at human EP1 expressed in HEK293 cells assessed as increase in ... 35124532
Homo sapiens IC50 = 0.39 nM 9.41 In vitro inhibition of collagen (0.66 ug/mL)-induced platelet aggregation in hum... 2419560
Homo sapiens IC50 = 0.39 nM 9.41 In vitro inhibition of thrombin (0.14 IU/mL)-induced platelet aggregation in hum... 2419560
Prostacyclin receptor EC50 = 0.4 nM 9.4 Agonist activity at human IP expressed in HEK293 cells assessed as increase in c... 35124532
Prostacyclin receptor EC50 = 0.69 nM 9.16 Agonist activity at recombinant rat IP receptor expressed in CHO-K1 cells assess... 28072531
Homo sapiens IC50 = 0.82 nM 9.09 In vitro inhibition of ADP (0.5 x 10E-9 M)-induced platelet aggregation in human... 2419560
Prostacyclin receptor Ki = 1.0 nM 9.0 Displacement of [3H]-iloprost from recombinant rat IP receptor expressed in CHO-... 28072531
Homo sapiens IC50 = 1.4 nM 8.85 PGI-2 agonistic activity by measuring inhibition of 4 uM ADP-induced human plate... -
Homo sapiens IC50 = 1.4 nM 8.85 Inhibitory activity against ADP-induced platelet aggregation using human platele... -
Unchecked Ki = 1.6 nM 8.8 Displacement of [3H]-iloprost from recombinant monkey IP receptor expressed in C... 28072531
Unchecked Ki = 1.7 nM 8.77 Displacement of [3H]-iloprost from recombinant dog IP receptor expressed in CHO-... 28072531
Homo sapiens IC50 = 2.0 nM 8.7 In vitro inhibition of ADP-induced aggregation of human platelets 8254619
Homo sapiens IC50 = 2.0 nM 8.7 In vitro inhibition of 5.86 uM ADP-induced human platelet aggregation in platele... 7504734
Prostacyclin receptor EC50 = 2.4 nM 8.62 Agonist activity at recombinant human IP receptor expressed in CHO-K1 cells asse... 28072531
Homo sapiens IC50 = 2.5 nM 8.6 In vitro inhibition of ADP-induced platelet aggregation using human platelet ric... 14643308
Unchecked IC50 = 2.5 nM 8.6 In vitro inhibition of ADP-induced platelet aggregation in human platelet rich p... 15935660
Cell line IC50 = 2.5 nM 8.6 Inhibition concentration against ADP-induced platelet aggregation using human pl... 15914004
Prostacyclin receptor Ki = 3.2 nM 8.49 Displacement of [3H]-iloprost from recombinant human IP receptor expressed in CH... 28072531
Prostacyclin receptor Ki = 4.8 nM 8.32 Binding affinity to human PGI2 receptor by radioligand displacement assay 23466604

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15920768 10.1002/jps.20373 ADMET 8
28072531 10.1021/acs.jmedchem.6b00871 Prostacyclin receptor 5
18426954 10.1124/dmd.108.020479 ADMET 4
20014752 10.1021/tx900326k Hepatotoxicity 3
2419560 10.1021/jm00153a001 Homo sapiens 3
23466604 10.1016/j.ejmech.2013.01.044 Prostacyclin receptor 2
28072531 10.1021/acs.jmedchem.6b00871 Unchecked 2
28072531 10.1021/acs.jmedchem.6b00871 Prostaglandin E2 receptor EP3 subtype 2
7504734 10.1021/jm00076a018 Homo sapiens 2
- 10.6019/CHEMBL5303304 HEK-293T 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.1016/S0960-894X(00)80165-1 Unchecked 2
- 10.1016/S0960-894X(00)80165-1 Homo sapiens 2
- 10.1016/S0960-894X(00)80165-1 Prostacyclin receptor 2
28072531 10.1021/acs.jmedchem.6b00871 Prostaglandin D2 receptor 2
28072531 10.1021/acs.jmedchem.6b00871 ADMET 2
18983139 10.1021/jm8007618 Prostacyclin receptor 2
- 10.1016/0960-894X(95)00167-R Prostacyclin receptor 1

Data from ChEMBL 36 via Core Engine