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Compound Detail

CHEMBL495

ALPROSTADIL
💊 Approved Drug
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💊 Approved Drug
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL495
Name ALPROSTADIL
Phase Approved
Structure Type MOL
InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N
Therapeutic ✓ Yes

Known Names

Alprostadil Caverject Caverject impulse Edex NSC-165559 ONO-1608 Pge1 Prostaglandin e1 Prostin vr Prostin vr pediatric U-10,136 U-10136 +5 more
13
Targets
36
Activities
3
Assay Types
1
PK Parameters
20
Publications
17
Known Names
14
Indications
2
Mechanisms

Molecular Properties

354.5
MW (Da)
3.48
ALogP
4
HBA
3
HBD
94.8
PSA (Ų)
0.35
QED
0
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -dil; -prost-
USAN Year 1977

Extended Properties

Molecular Formula C20H34O5
MW 354.49
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 1.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Prostanoid EP1 receptor agonist AGONIST Prostaglandin E2 receptor EP1 subtype ✓ ✓
Prostanoid EP2 receptor agonist AGONIST Prostaglandin E2 receptor EP2 subtype ✓ ✓

Indications

Cardiovascular Diseases Ductus Arteriosus, Patent Erectile Dysfunction Heart Failure Macular Degeneration Prostatic Neoplasms, Castration-Resistant Acute Kidney Injury Arteriosclerosis Obliterans Optic Neuropathy, Ischemic Peripheral Arterial Disease Peripheral Vascular Diseases Respiratory Distress Syndrome Severe Acute Respiratory Syndrome Sexual Dysfunction, Physiological

ATC Classification

C01EA01
alprostadil
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
G04BE01
alprostadil
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Drug Warnings

Black Box Warning
General Warning
Country: United States
Black Box Warning
teratogenicity
Country: United States

Activity Summary

Ki 19 meas. best 8.51
EC50 12 meas. best 8.74
IC50 5 meas. best 7.45

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostacyclin receptor
CHEMBL1995
 EC50 8.74 8.74 1.8 1
Prostaglandin E2 receptor EP4 subtype
CHEMBL2489
 EC50 8.6 8.5467 2.5 3
Prostaglandin E2 receptor EP2 subtype
CHEMBL2488
 EC50 8.59 8.59 2.6 1
Prostaglandin E2 receptor EP4 subtype
CHEMBL2489
 Ki 8.51 8.4875 3.1 4
Prostaglandin E2 receptor EP3 subtype
CHEMBL4336
 Ki 8.3 8.3 5.0 4
Prostaglandin E2 receptor EP1 subtype
CHEMBL2181
 Ki 8.22 7.635 6.0 4
Prostaglandin E2 receptor EP2 subtype
CHEMBL2488
 Ki 7.66 7.375 22.0 4
Solute carrier organic anion transporter family member 2B1
CHEMBL2073698
 IC50 7.45 7.45 35.8 1
Homo sapiens
CHEMBL372
 IC50 7.16 7.16 70.0 1
Prostacyclin receptor
CHEMBL1995
 Ki 6.82 6.82 150.0 3
Prostacyclin receptor
CHEMBL1995
 IC50 5.85 5.85 1400.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.64 5.64 2300.0 1
Nuclear receptor subfamily 4 group A member 2
CHEMBL3879839
 EC50 5.52 5.52 3000.0 2
Nuclear receptor subfamily 4 group A member 2
CHEMBL4523278
 EC50 5.52 5.52 3000.0 2
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
 EC50 5.52 5.52 3000.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 5.27 5.27 5390.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 4.57 4.57 26900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6900.0 L/hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostacyclin receptor EC50 = 1.8 nM 8.74 Effective concentration which increases intracellular c-AMP production in human ... 11454472
Prostaglandin E2 receptor EP4 subtype EC50 = 2.5 nM 8.6 Effective concentration which increases intracellular c-AMP production in mouse ... 11454473
Prostaglandin E2 receptor EP4 subtype EC50 = 2.5 nM 8.6 Effective concentration for increased intracellular c-AMP production by mouse Pr... 11454474
Prostaglandin E2 receptor EP2 subtype EC50 = 2.6 nM 8.59 Effective concentration which increases intracellular c-AMP production in mouse ... 11454472
Prostaglandin E2 receptor EP4 subtype Ki = 3.1 nM 8.51 Affinity for mouse Prostanoid EP4 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP4 subtype Ki = 3.3 nM 8.48 Binding affinity towards mouse Prostanoid EP4 receptor in CHO cells. 11454472
Prostaglandin E2 receptor EP4 subtype Ki = 3.3 nM 8.48 Affinity for mouse Prostanoid EP4 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP4 subtype Ki = 3.3 nM 8.48 Evaluated for its competitive binding affinity towards mouse Prostanoid EP4 rece... 11454473
Prostaglandin E2 receptor EP4 subtype EC50 = 3.6 nM 8.44 Effective concentration for increased intracellular c-AMP production by mouse Pr... 11454474
Prostaglandin E2 receptor EP3 subtype Ki = 5.0 nM 8.3 Affinity for mouse Prostanoid EP3 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP3 subtype Ki = 5.0 nM 8.3 Affinity for mouse Prostanoid EP3 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP3 subtype Ki = 5.0 nM 8.3 Evaluated for its competitive binding affinity towards mouse Prostanoid EP3 rece... 11454473
Prostaglandin E2 receptor EP3 subtype Ki = 5.0 nM 8.3 Binding affinity towards mouse Prostanoid EP3 receptor in CHO cells. 11454472
Prostaglandin E2 receptor EP1 subtype Ki = 6.0 nM 8.22 Affinity for mouse Prostanoid EP1 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP2 subtype Ki = 22.0 nM 7.66 Affinity for mouse Prostanoid EP2 receptor expressed in CHO cells 11454474
Prostaglandin E2 receptor EP1 subtype Ki = 22.0 nM 7.66 Evaluated for its competitive binding affinity towards mouse Prostanoid EP1 rece... 11454473
Prostaglandin E2 receptor EP1 subtype Ki = 22.0 nM 7.66 Affinity for mouse Prostanoid EP1 receptor expressed in CHO cells 11454474
Solute carrier organic anion transporter family member 2B1 IC50 = 35.8 nM 7.45 TP_TRANSPORTER: inhibition of PGD2 uptake in Xenopus laevis oocytes 10973807
Prostaglandin E2 receptor EP2 subtype Ki = 41.0 nM 7.39 Evaluated for its competitive binding affinity towards mouse Prostanoid EP2 rece... 11454473
Prostaglandin E2 receptor EP2 subtype Ki = 41.0 nM 7.39 Affinity for mouse Prostanoid EP2 receptor expressed in CHO cells 11454474

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058577 U2OS 304
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2909735 10.1021/jm00121a041 Unchecked 11
- 10.6019/CHEMBL5058564 U2OS 10
198545 10.1021/jm00220a013 Unchecked 8
198546 10.1021/jm00220a014 Unchecked 7
- 10.6019/CHEMBL5303304 U2OS 7
- 10.6019/CHEMBL5303304 Fibroblast 7
35797147 10.1021/acs.jmedchem.2c00585 Nuclear receptor subfamily 4 group A member 2 6
- 10.6019/CHEMBL5303304 HEK-293T 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
- 10.6019/CHEMBL5058564 HEK-293T 5
191613 10.1021/jm00214a016 Unchecked 5
189028 10.1021/jm00211a007 Unchecked 4

Data from ChEMBL 36 via Core Engine