Alprostadil

Summary

Alprostadil (CHEMBL495) is an approved small-molecule platelet aggregation inhibitor (ATC G04BE01) targeting PTGDR, PTGER1, and PTGER2; indicated across 14 conditions including erectile dysfunction and cardiovascular disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: G04BE01 (+1 more)
• Targets: 10 (PTGDR, PTGER1, PTGER2…)
• Indications: 14 conditions
• Clinical trials: 32
• Chemistry: 354.5 Da · C20H34O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL495
Name	Alprostadil
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5280723
ChEBI	CHEBI:15544
ATC	G04BE01, C01EA01
Molecular formula	C20H34O5
Molecular weight	354.5
InChIKey	GMVPRGQOIOIIMI-DWKJAMRDSA-N

SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O

IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid

Pharmacological roles (ChEBI): platelet aggregation inhibitor, vasodilator agent, anticoagulant.

Other ChEBI roles (chemical / environmental): human metabolite.

Also known as: Alprostadil, Caverject, Caverject impulse, Edex, NSC-165559, ONO-1608, Pge1, Prostaglandin e1, Prostin vr, Prostin vr pediatric, U-10,136, U-10136

Patent coverage: 4,205 distinct patent families (13,450 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
PTGDR	DP1 receptor	Full agonist	7.3	0.4%	Q13258
PTGER1	EP1 receptor	Full agonist	6.8	0.4%	P34995
PTGER2	EP2 receptor	Full agonist	8.04	0.1%	P43116
PTGER3	EP3 receptor	Full agonist	9	2.6%	P43115
PTGER4	EP4 receptor	Full agonist	8.8	0.5%	P35408
PTGIR	IP receptor	Full agonist	6.82	0.2%	P43119
CATSPER1	CatSper1	Full agonist	6.3	1.8%	Q8NEC5
CATSPER2	CatSper2	Full agonist	6.3	0.2%	Q96P56
CATSPER3	CatSper3	Full agonist	6.3	0.6%	Q86XQ3
CATSPER4	CatSper4	Full agonist	6.3	0.2%	Q7RTX7

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: ATP-binding cassette sub-family C member 4, Prostacyclin receptor, Retinoic acid receptor gamma, Retinoic acid receptor beta, D(1A) dopamine receptor, Solute carrier organic anion transporter family member 2B1, Prostaglandin E2 receptor EP1 subtype, Prostaglandin E2 receptor EP2 subtype, Prostaglandin E2 receptor EP4 subtype, Nuclear receptor subfamily 4 group A member 2.

Bioactivity

ChEMBL activities: 34 potent at pChembl ≥ 5 of 37 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGIR	8.74	EC50	1.8	nM	CHEMBL_ACT_92305
P32240	8.6	EC50	2.5	nM	CHEMBL_ACT_1149944
P32240	8.6	EC50	2.5	nM	CHEMBL_ACT_596637
Q62053	8.59	EC50	2.6	nM	CHEMBL_ACT_92304
P32240	8.51	Ki	3.1	nM	CHEMBL_ACT_1181428
P32240	8.48	Ki	3.3	nM	CHEMBL_ACT_1149942
P32240	8.48	Ki	3.3	nM	CHEMBL_ACT_596635
P32240	8.48	Ki	3.3	nM	CHEMBL_ACT_92302
P32240	8.44	EC50	3.6	nM	CHEMBL_ACT_1181430
P30557	8.3	Ki	5	nM	CHEMBL_ACT_1149941
P30557	8.3	Ki	5	nM	CHEMBL_ACT_1181427
P30557	8.3	Ki	5	nM	CHEMBL_ACT_596634
P30557	8.3	Ki	5	nM	CHEMBL_ACT_92301
P35375	8.22	Ki	6	nM	CHEMBL_ACT_1181425
DRD1	8	AC50	10	nM	CHEMBL_ACT_25180682
P35375	7.66	Ki	22	nM	CHEMBL_ACT_1149939
Q62053	7.66	Ki	22	nM	CHEMBL_ACT_1181426
P35375	7.66	Ki	22	nM	CHEMBL_ACT_596632
Q9JHI3	7.45	IC50	35.8	nM	CHEMBL_ACT_11000836
Q62053	7.39	Ki	41	nM	CHEMBL_ACT_1149940
Q62053	7.39	Ki	41	nM	CHEMBL_ACT_596633
Q62053	7.06	Ki	87	nM	CHEMBL_ACT_92300
P35375	7	Ki	100	nM	CHEMBL_ACT_92299
PTGIR	6.82	Ki	150	nM	CHEMBL_ACT_1149943
PTGIR	6.82	Ki	150	nM	CHEMBL_ACT_596636
PTGIR	6.82	Ki	150	nM	CHEMBL_ACT_92303
PTGIR	5.85	IC50	1400	nM	CHEMBL_ACT_768940
ABCC4	5.64	IC50	2300	nM	CHEMBL_ACT_18130904
NR4A2	5.52	EC50	3000	nM	CHEMBL_ACT_24824495
NR4A2	5.52	EC50	3000	nM	CHEMBL_ACT_24824497

Target pathways

Aggregated over 10 target gene(s): PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGIR, CATSPER1, CATSPER2, CATSPER3, CATSPER4.

Top Reactome pathways

6 total, by targets touching each:

Pathway	Targets	Genes
Prostanoid ligand receptors	6	PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGIR
Sperm Motility And Taxes	4	CATSPER1, CATSPER2, CATSPER3, CATSPER4
G alpha (s) signalling events	4	PTGDR, PTGER2, PTGER4, PTGIR
Prostacyclin signalling through prostacyclin receptor	1	PTGIR
G alpha (q) signalling events	1	PTGER1
G alpha (i) signalling events	1	PTGER3

Dominant GO biological processes

GO term	Targets
inflammatory response	6
G protein-coupled receptor signaling pathway	6
positive regulation of cytosolic calcium ion concentration	6
signal transduction	6
adenylate cyclase-activating G protein-coupled receptor signaling pathway	5
calcium ion transport	4
spermatogenesis	4
cell differentiation	4
flagellated sperm motility	4
monoatomic ion transport	4
monoatomic ion transmembrane transport	4
transmembrane transport	4
calcium ion transmembrane transport	4
response to lipopolysaccharide	3
sperm capacitation	3

Indications & clinical

Indications

14 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
erectile dysfunction	4	MONDO:0005362	EFO:0004234
cardiovascular disorder	4	MONDO:0004995	EFO:0000319
patent ductus arteriosus	4	MONDO:0011827	HP:0001643
heart failure	3	MONDO:0005252	EFO:0003144
macular degeneration	3	MONDO:0003004	EFO:0009606
physiological sexual disorder	2	MONDO:0002134	EFO:0004714
peripheral vascular disease	2	MONDO:0005294	EFO:0003875
arteriosclerosis obliterans	2	MONDO:0006659	EFO:1000820
anterior ischemic optic neuropathy	2	MONDO:0006649	EFO:1000809
peripheral arterial disease	2	MONDO:0005386	EFO:0004265
severe acute respiratory syndrome	2	MONDO:0005091	MONDO:0100096
adult acute respiratory distress syndrome	2	MONDO:0100130	MONDO:0100130
acute kidney injury	2	MONDO:0002492	HP:0001919

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 32.

Phase distribution

Phase	Trials
PHASE4	12
PHASE2	9
Not specified	5
PHASE1	3
PHASE3	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00596752	PHASE4	COMPLETED	Alprostadil in Peripheral Arterial Occlusive Disease (PAOD) Stage IV
NCT00733434	PHASE4	UNKNOWN	The Use of Prostaglandin E1 in Head and Neck Microsurgery
NCT01722513	PHASE4	UNKNOWN	Efficacy and Safety of Alprostadil Prevent Contrast Induced Nephropathy
NCT01776320	PHASE4	WITHDRAWN	Efficacy, Safety and Satisfaction of VITAROS (Transdermal Topical Alprostadil) in Men With Erectile Dysfunction
NCT03252626	PHASE4	UNKNOWN	Study on the Efficacy of Alprostadil Injection in Patients With Acute Ischemic Stroke
NCT03252665	PHASE4	UNKNOWN	Efficacy of Intracoronary Infusion of Different Medicine in STEMI Patients Undergoing Primary PCI
NCT03296670	PHASE4	COMPLETED	Efficacy of Intracoronary Infusion of Different Medicine in STEMI Patients With CSFP
NCT03682952	PHASE4	UNKNOWN	Evaluation of Nail Fold Microcirculation in CKD
NCT03892447	PHASE4	UNKNOWN	The Comparative Effectiveness of Alprostadil,Sodium Ferulate and Dopamine in Pediatric Acute Kidney Injury
NCT04312555	PHASE4	UNKNOWN	Alprostadil as an Adjuvant Therapy With Indirect Angiosomal Revascularization in Critical Limb Ischemia.
NCT07503184	PHASE4	COMPLETED	Intravenous Dexamethasone for Inducing Labor in Women With Term Pregnancy and Pre-Labour Rupture of Membranes
NCT07604051	PHASE4	COMPLETED	Termination of Pregnancy in Previous Scarred Uterus: PGE1 Versus Cervical Folleys
NCT00610051	PHASE3	NOT_YET_RECRUITING	ALP-1 Continuous Intravenous Infusion to Maintain Clinical Stability in Advanced Heart Failure
NCT00544076	PHASE3	TERMINATED	ED Recovery in Men Age </=65 Treated With Bilateral Nerve Sparing Robotic Assisted Prostatectomy for Prostate Cancer
NCT02223949	PHASE2/PHASE3	UNKNOWN	Labor Induction and Maternal BMI, Comparison of Different Pre-induction Cervical Ripening Methods
NCT00080808	PHASE2	COMPLETED	Nerve-Sparing Radical Prostatectomy With or Without Nerve Grafting Followed by Standard Therapy for Erectile Dysfunction in Treating Patients With Localized Prostate Cancer
NCT00324948	PHASE2	COMPLETED	Topical Alprostadil for Female Sexual Arousal Disorder
NCT01467076	PHASE2	TERMINATED	Inhaled Prostaglandin E1 (IPGE1) for Hypoxemic Respiratory Failure (NHRF)
NCT02228850	PHASE2	COMPLETED	Study of Acute Peripheral Vascular Effects, Safety and Tolerability in Subjects With Raynaud’s Phenomenon Secondary to Systemic Sclerosis
NCT02877173	PHASE2	UNKNOWN	A Safety/Efficacy Study of Alprostadil Liposomes for Injection to Treat Lower Extremity Arteriosclerosis Obliterans
NCT02895373	PHASE2	TERMINATED	PGE1 as Additive Anticoagulant in ECMO-Therapy
NCT03851562	PHASE2	UNKNOWN	Intravenous Infusion of Prostaglandins as Therapy in Patients With Anterior Non-arteritic Ischemic Optic Neuropathy
NCT04197323	PHASE2	UNKNOWN	Alprostadil Liposomes for Injection for Lower Extremity Arteriosclerosis Obliteran
NCT04536363	PHASE2	WITHDRAWN	Cri Analog PG1 Effectiveness and Safety in Covid-19
NCT02889822	PHASE1	COMPLETED	The Tolerability of Alprostadil Liposome for Injection in Healthy Adult Volunteers
NCT03669562	PHASE1	UNKNOWN	The Safety and Tolerability of Alprostadil Liposome for Injection in Healthy Adult Volunteers
NCT04054115	PHASE1	TERMINATED	Acute Effects of the Prostaglandin (Alprostadil) on Cerebral and Pulmonary Flow
NCT06768177	Not specified	ENROLLING_BY_INVITATION	Platelet Rich Plasma (PRP) as Terapeutical Option in Erectil Disfunction (DE)
NCT00314548	Not specified	COMPLETED	Inhaled Prostacyclin for Adult Respiratory Distress Syndrome (ARDS) and Pulmonary Hypertension
NCT00507286	Not specified	UNKNOWN	Efficacy and Safety Study of Combined Oral and Injection Therapy for Erectile Dysfunction
NCT03027219	Not specified	COMPLETED	Blood Flow Change After Free Flap Surgery in Diabetic Patients
NCT04496050	Not specified	UNKNOWN	Effects of Prostaglandin E1 Treatment on Pyloric Wall in Newborns

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

35 molecules share ≥1 primary target. Top 35 by shared-target count:

Molecule	Source	Status	Shared targets
dinoprostone	ChEMBL + PubChem	Phase 4 (approved)	CATSPER1, CATSPER4, PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGIR
DINOPROST	ChEMBL + PubChem	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGIR
RALINEPAG	ChEMBL	Phase 3	PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGIR
ILOPROST	ChEMBL + PubChem	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGER3, PTGIR
LAROPIPRANT	ChEMBL	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGER3, PTGIR
Grapiprant	ChEMBL + PubChem	Phase 2 (approved)	PTGER1, PTGER2, PTGER3, PTGER4, PTGIR
omidenepag isopropyl	ChEMBL + PubChem	Phase 4 (approved)	PTGER1, PTGER2, PTGER3, PTGER4
TREPROSTINIL	ChEMBL + PubChem	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGIR
Cloprostenol	ChEMBL + PubChem	Phase 2 (approved)	PTGDR, PTGER1, PTGER2, PTGER3
Omidenepag	ChEMBL + PubChem	Phase 2 (approved)	PTGER1, PTGER2, PTGER3, PTGER4
Belzutifan	PubChem	Approved	PTGDR, PTGER2, PTGER3, PTGIR
SELEXIPAG	ChEMBL	Phase 4 (approved)	PTGDR, PTGIR
SETIPIPRANT	ChEMBL	Phase 3	PTGDR, PTGER2
TIMAPIPRANT	ChEMBL	Phase 3	PTGDR, PTGIR
BUTAPROST	ChEMBL	Phase 2	PTGER2, PTGIR
LASELIPAG	ChEMBL	Phase 2	PTGDR, PTGIR
PALUPIPRANT	ChEMBL	Phase 2	PTGER2, PTGER4
Progesterone	PubChem	Approved	CATSPER1, CATSPER4
RAMATROBAN	ChEMBL	Phase 4 (approved)	PTGDR
ASAPIPRANT	ChEMBL	Phase 3	PTGDR
SEPETAPROST	ChEMBL	Phase 3	PTGER3
BGC-20-1531	ChEMBL	Phase 2	PTGER4
BGC-20-1531 FREE BASE	ChEMBL	Phase 2	PTGER4
BI-671800	ChEMBL	Phase 2	PTGDR
BMS-986310	ChEMBL	Phase 2	PTGER4
EVATANEPAG	ChEMBL	Phase 2	PTGER2
FLUPROSTENOL	ChEMBL	Phase 2	PTGER3
PINADOLINE	ChEMBL	Phase 2	PTGER2
TAPRENEPAG	ChEMBL	Phase 2	PTGER2
TAPRENEPAG ISOPROPYL	ChEMBL	Phase 2	PTGER2
VIDUPIPRANT	ChEMBL	Phase 2	PTGDR
epoprostenol	PubChem	Approved	PTGIR
Indomethacin	PubChem	Approved	PTGIR
Misoprostol	PubChem	Approved	PTGER2
Yohimbine	PubChem	Approved	PTGIR