Dinoprostone

Summary

Dinoprostone (CHEMBL548) is an approved small-molecule oxytocic (ATC G02AD02) targeting PTGDR, PTGDR2, and PTGER1; indicated across 5 conditions including fetal growth restriction and benign muscle neoplasm.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: G02AD02
• Targets: 12 (PTGDR, PTGDR2, PTGER1…)
• Indications: 5 conditions
• Clinical trials: 65
• Chemistry: 352.5 Da · C20H32O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL548
Name	Dinoprostone
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5280360
ChEBI	CHEBI:15551
ATC	G02AD02
Molecular formula	C20H32O5
Molecular weight	352.5
InChIKey	XEYBRNLFEZDVAW-ARSRFYASSA-N

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

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

ChEBI definition: Prostaglandin F2α in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.

Pharmacological roles (ChEBI): oxytocic.

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

Also known as: Cervidil, Dinoprostona, Dinoprostone, Dinoprostone beta-cyclodextrin clathrate, Enzaprost e, Minprostin e2, NSC-165560, NSC-196514, Prepidil, Propess, Prostaglandin e2, Prostin e2

Patent coverage: 6,818 distinct patent families (14,939 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	0.4%	Q13258
PTGDR2	DP2 receptor	Full agonist	5.3	0%	Q9Y5Y4
PTGER1	EP1 receptor	Full agonist	8	0.4%	P34995
PTGER2	EP2 receptor	Full agonist	8.3	0.1%	P43116
PTGER3	EP3 receptor	Full agonist	8.68	2.6%	P43115
PTGER4	EP4 receptor	Full agonist	6.05	0.5%	P35408
PTGFR	FP receptor	Full agonist	6.9	0%	P43088
TBXA2R	TP receptor	Full agonist	4.5	0.2%	P21731
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: 26 (assay-derived). Sample: 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Prostaglandin E2 receptor EP1 subtype, Prostaglandin E2 receptor EP4 subtype, Prostaglandin E2 receptor EP2 subtype, Thyrotropin receptor, Prostaglandin F2-alpha receptor, Prostacyclin receptor, Estrogen receptor, Thromboxane A2 receptor, Progesterone receptor.

Bioactivity

ChEMBL activities: 77 potent at pChembl ≥ 5 of 87 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGER4	10.7	EC50	0.02	nM	CHEMBL_ACT_19177462
PTGER4	9.96	Ki	0.11	nM	CHEMBL_ACT_19177444
PTGER4	9.85	Ki	0.14	nM	CHEMBL_ACT_26333228
PTGER4	9.77	Ki	0.17	nM	CHEMBL_ACT_13342005
Q62928	9.7	EC50	0.2	nM	CHEMBL_ACT_2650974
PTGER4	9.49	IC50	0.32	nM	CHEMBL_ACT_26333173
PTGER3	9.48	Ki	0.33	nM	CHEMBL_ACT_2033741
PTGER3	9.48	Ki	0.33	nM	CHEMBL_ACT_2090626
PTGER4	9.35	Ki	0.45	nM	CHEMBL_ACT_13340292
PTGER4	9.35	IC50	0.45	nM	CHEMBL_ACT_13342077
PTGER4	9.26	IC50	0.55	nM	CHEMBL_ACT_16838447
PTGER4	9.23	EC50	0.58	nM	CHEMBL_ACT_19177450
PTGER4	9.15	IC50	0.7	nM	CHEMBL_ACT_1192140
P43114	9.15	EC50	0.7	nM	CHEMBL_ACT_2650975
PTGER4	9.1	Ki	0.79	nM	CHEMBL_ACT_2033751
PTGER4	9.1	Ki	0.79	nM	CHEMBL_ACT_2050964
PTGER4	9.1	Ki	0.79	nM	CHEMBL_ACT_2090582
PTGER3	9.03	IC50	0.94	nM	CHEMBL_ACT_3302228
PTGER2	8.99	Ki	1.03	nM	CHEMBL_ACT_19177432
PTGER4	8.96	IC50	1.1	nM	CHEMBL_ACT_13340357
PTGER1	8.96	IC50	1.1	nM	CHEMBL_ACT_3302230
PTGER2	8.77	Ki	1.7	nM	CHEMBL_ACT_13342006
PTGER2	8.72	EC50	1.9	nM	CHEMBL_ACT_16584671
PTGER4	8.72	Ki	1.9	nM	CHEMBL_ACT_2381330
PTGER2	8.68	EC50	2.1	nM	CHEMBL_ACT_14726575
P43114	8.68	IC50	2.1	nM	CHEMBL_ACT_2650972
PTGER2	8.66	IC50	2.2	nM	CHEMBL_ACT_13336175
PTGER3	8.66	Ki	2.17	nM	CHEMBL_ACT_19177438
PTGER3	8.6	EC50	2.5	nM	CHEMBL_ACT_16584551
PTGER2	8.59	IC50	2.6	nM	CHEMBL_ACT_16501801

Target pathways

Aggregated over 12 target gene(s): PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R, CATSPER1, CATSPER2, CATSPER3, CATSPER4.

Top Reactome pathways

16 total, by targets touching each:

Pathway	Targets	Genes
Prostanoid ligand receptors	8	PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R
Sperm Motility And Taxes	4	CATSPER1, CATSPER2, CATSPER3, CATSPER4
G alpha (q) signalling events	3	PTGER1, PTGFR, TBXA2R
G alpha (s) signalling events	3	PTGDR, PTGER2, PTGER4
G alpha (i) signalling events	2	PTGDR2, PTGER3
Hemostasis	1	TBXA2R
Signal Transduction	1	TBXA2R
Signaling by GPCR	1	TBXA2R
Class A/1 (Rhodopsin-like receptors)	1	TBXA2R
GPCR downstream signalling	1	TBXA2R
Eicosanoid ligand-binding receptors	1	TBXA2R
Signal amplification	1	TBXA2R
G alpha (12/13) signalling events	1	TBXA2R
Thromboxane signalling through TP receptor	1	TBXA2R
GPCR ligand binding	1	TBXA2R
Platelet activation, signaling and aggregation	1	TBXA2R

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	8
signal transduction	8
inflammatory response	7
positive regulation of cytosolic calcium ion concentration	7
adenylate cyclase-activating G protein-coupled receptor signaling pathway	6
response to lipopolysaccharide	4
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
cellular response to prostaglandin D stimulus	3

Indications & clinical

Indications

5 indications (0 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
fetal growth restriction	3	MONDO:0005030	EFO:0000495
benign muscle neoplasm	3	MONDO:0003061	MONDO:0003061

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

Clinical trials

Total trials: 65.

Phase distribution

Phase	Trials
Not specified	23
PHASE3	18
PHASE4	17
PHASE2	5
PHASE2/PHASE3	1
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01190163	PHASE4	TERMINATED	Open Label Comparative Trial of Dinoprostone Plus or Minus Oxytocin Versus Oxytocin Alone in Cervical Ripening for Labor Induction
NCT01620814	PHASE4	UNKNOWN	Intravaginal Misoprostol Versus Dinoprostone Before Diagnostik Hysteroscopy
NCT01720394	PHASE4	UNKNOWN	Efficacy of Induction of Labor on Term Using a Double Balloon Catheter Compared to Dinoprostone Vaginal-insert
NCT02801227	PHASE4	UNKNOWN	Oxytocin vs. Prostaglandin for Induction of Labor in Primiparas With Prelabor Rupture of Membrane and Low Bishop
NCT02902653	PHASE4	UNKNOWN	Efficacy and Safety of Hourly Titrated Misoprostol Versus Vaginal Dinoprostone and Misoprostol for Cervical Ripening and Labor Induction
NCT03744364	PHASE4	COMPLETED	Low-dose Vaginal Misoprostol Versus Vaginal Dinoprostone Insert for Induction of Labor
NCT04042974	PHASE4	UNKNOWN	Vaginal Dinoprostone Prior to Diagnostic Office Hysteroscopy in Primarily Infertile Patients
NCT04044079	PHASE4	COMPLETED	Vaginal Dinoprostone Versus Vaginal Misoprostol Prior to Diagnostic Office Hysteroscopy in Postmenopausal Patients
NCT04045548	PHASE4	COMPLETED	Vaginal Dinoprostone Administration Prior to Insertion Levonorgestrel-releasing Intrauterine System in Women With no Previous Vaginal Delivery
NCT04046302	PHASE4	COMPLETED	Vaginal Dinoprostone Administration Prior to an Intrauterine Device Insertion in Multiparous Women.
NCT04079140	PHASE4	COMPLETED	Vaginal Dinoprostone Administration Prior to Intrauterine Device Insertion
NCT04080336	PHASE4	COMPLETED	Comparison of Vaginal Misoprostol and Dinoprostone Prior to Copper Intrauterine Device Insertion in Nulliparous Women
NCT04080349	PHASE4	UNKNOWN	Comparison of Vaginal Misoprostol and Dinoprostone Prior to Copper Intrauterine Device Insertion in Women Delivered Only by Cesarean Delivery
NCT04280874	PHASE4	COMPLETED	Induction of Labor in Term Pregnancies With Unfavourable Cervix
NCT04339361	PHASE4	UNKNOWN	Comparative Efficacy of Lidocaine Spray Versus Vaginal Dinoprostone in IUD Insertion
NCT04357002	PHASE4	UNKNOWN	Intravenous Tranexamic Acid Versus Vaginal Dinoprostone in Abdominal Myomectomy
NCT05430711	PHASE4	UNKNOWN	Dinoprostone Induction vs. Expectant Management After PROM at Term
NCT00545194	PHASE3	WITHDRAWN	Cervical Ripening Before Induction of Labour at Term: a Randomised Comparison of Prostin vs Propess
NCT00602095	PHASE3	COMPLETED	Labour Induction With Misoprostol, Dinoprostone and Bard Catheter
NCT01099280	PHASE3	COMPLETED	Induction of Labor in Term Premature Rupture of Membranes: A Comparison Between Oxytocin and Dinoprostone Followed Six Hours Later by Oxytocin
NCT01635439	PHASE3	COMPLETED	Prostin and Propess in Induction of Labor
NCT02036437	PHASE3	UNKNOWN	Titrated Oral Misoprostol Compared to Vaginal Dinoprostone for Induction of Labor
NCT02684305	PHASE3	UNKNOWN	Stepwise Labor Induction Following Failure of Prostaglandin Vaginal Insert for Labor Induction
NCT02888041	PHASE3	TERMINATED	Is There an Interest in Repeating the Vaginal Administration of Dinoprostone (Propess®), to Promote Induction of Labor of Pregnant Women at Term?
NCT03001661	PHASE3	COMPLETED	An RCT of a Synthetic Osmotic Cervical Dilator for Induction of Labour in Comparison to Dinoprostone Vaginal insErt
NCT03067597	PHASE3	COMPLETED	An Open-label Trial Investigating the Efficacy and Safety of a Vaginal Insert in Pregnant Women at Term
NCT03067727	PHASE3	COMPLETED	A Randomised Trial Investigating the Efficacy and Safety of a Vaginal Insert in Pregnant Women at Term
NCT03320187	PHASE2/PHASE3	COMPLETED	Nitroglycerin Skin Patches for Facilitating Cervical Ripening: A Randomized Controlled Trial
NCT03489928	PHASE3	COMPLETED	Misoprostol Labour Induction Study
NCT03686085	PHASE3	COMPLETED	Vaginal Dinoprostone Administration Prior to a T380A Intrauterine Device Insertion in Nulliparous Women.
NCT04080323	PHASE3	COMPLETED	Single-dose Vaginal Dinoprostone and Hysterectomy
NCT04080375	PHASE3	UNKNOWN	Preoperative Vaginal Dinoprostone Prior to Abdominal Myomectomy
NCT04301349	PHASE3	UNKNOWN	Dinoprostone vs Misoprostol Before LNG-IUD Insertion
NCT04340778	PHASE3	UNKNOWN	Comparative Safety and Efficacy of Vaginal Dinoprostone Versus Lidocaine-prilocaine Cream in Copper IUD Insertion
NCT05761418	PHASE3	COMPLETED	Preoperative Vaginal Dinoprostone Versus Misoprostone in Abdominal Myomectomy
NCT05774236	PHASE3	COMPLETED	Cook´s Balloon Versus Dinoprostone for Labor Induction of Term Pregnancies With Fetal Growth Restriction
NCT00432588	PHASE1/PHASE2	UNKNOWN	Comparing the Effect of Vaginal Misoprostol With Dinoprostone in Term Pregnancies
NCT01765881	PHASE2	COMPLETED	Comparison Between 25 µg Vaginal Misoprostol vs Slow Release Pessary PGE2
NCT02856724	PHASE2	COMPLETED	Early Amniotomy After Vaginal Prostaglandin E2 for Induction of Labor at Term: a Randomized Clinical Trial
NCT02861079	PHASE2	COMPLETED	Combined Foley Catheter Balloon and PGE2 Vaginal Ovule for Induction of Labor at Term: A Randomized Study

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

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.

315 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
DINOPROST	ChEMBL + PubChem	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R
LAROPIPRANT	ChEMBL	Phase 4 (approved)	PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGFR, TBXA2R
Cloprostenol	ChEMBL + PubChem	Phase 2 (approved)	PTGDR, PTGER1, PTGER2, PTGER3, PTGFR, TBXA2R
Grapiprant	ChEMBL + PubChem	Phase 2 (approved)	PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R
RALINEPAG	ChEMBL	Phase 3	PTGDR, PTGER1, PTGER2, PTGER3, PTGER4
Belzutifan	PubChem	Approved	PTGDR, PTGER2, PTGER3, PTGFR, TBXA2R
ILOPROST	ChEMBL + PubChem	Phase 4 (approved)	PTGDR, PTGER1, PTGER2, PTGER3
omidenepag isopropyl	ChEMBL + PubChem	Phase 4 (approved)	PTGER1, PTGER2, PTGER3, PTGER4
Omidenepag	ChEMBL + PubChem	Phase 2 (approved)	PTGER1, PTGER2, PTGER3, PTGER4
Alprostadil	PubChem	Approved	CATSPER1, CATSPER4, PTGDR, PTGER2
RAMATROBAN	ChEMBL	Phase 4 (approved)	PTGDR, PTGDR2, TBXA2R
TREPROSTINIL	ChEMBL	Phase 4 (approved)	PTGDR, PTGER1, PTGER2
SETIPIPRANT	ChEMBL	Phase 3	PTGDR, PTGDR2, PTGER2
BI-671800	ChEMBL	Phase 2	PTGDR, PTGDR2, TBXA2R
INDOMETHACIN	ChEMBL + PubChem	Phase 4 (approved)	PTGDR2, TBXA2R
Tafluprost	ChEMBL + PubChem	Phase 4 (approved)	PTGFR, TBXA2R
SELEXIPAG	ChEMBL	Phase 4 (approved)	PTGDR, TBXA2R
SEPETAPROST	ChEMBL	Phase 3	PTGER3, PTGFR
TIMAPIPRANT	ChEMBL	Phase 3	PTGDR, PTGDR2
FLUPROSTENOL	ChEMBL	Phase 2	PTGER3, PTGFR
LASELIPAG	ChEMBL	Phase 2	PTGDR, TBXA2R
PALUPIPRANT	ChEMBL	Phase 2	PTGER2, PTGER4
VIDUPIPRANT	ChEMBL	Phase 2	PTGDR, PTGDR2
Latanoprostene Bunod	PubChem	Approved	PTGFR, TBXA2R
Progesterone	PubChem	Approved	CATSPER1, CATSPER4
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
DESLORATADINE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
ESTRADIOL VALERATE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
OLANZAPINE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
PIMAVANSERIN	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
POMALIDOMIDE	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
REGORAFENIB	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
RIFAMPIN	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
TEGASEROD	ChEMBL + PubChem	Phase 4 (approved)	TBXA2R
ACETYLCHOLINE	ChEMBL	Phase 4 (approved)	TBXA2R
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	TBXA2R
AMLODIPINE	ChEMBL	Phase 4 (approved)	TBXA2R
AMSACRINE	ChEMBL	Phase 4 (approved)	TBXA2R
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	TBXA2R
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	TBXA2R
AXITINIB	ChEMBL	Phase 4 (approved)	TBXA2R
BECLOMETHASONE DIPROPIONATE	ChEMBL	Phase 4 (approved)	TBXA2R
BENZBROMARONE	ChEMBL	Phase 4 (approved)	TBXA2R
BENZIODARONE	ChEMBL	Phase 4 (approved)	TBXA2R
BEXAROTENE	ChEMBL	Phase 4 (approved)	TBXA2R
BITHIONOL	ChEMBL	Phase 4 (approved)	TBXA2R
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	TBXA2R
BROMODIPHENHYDRAMINE	ChEMBL	Phase 4 (approved)	TBXA2R
CABOZANTINIB	ChEMBL	Phase 4 (approved)	TBXA2R
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	TBXA2R
CANNABIDIOL	ChEMBL	Phase 4 (approved)	TBXA2R
CERIVASTATIN	ChEMBL	Phase 4 (approved)	TBXA2R
CHLORMADINONE	ChEMBL	Phase 4 (approved)	TBXA2R
CHLORPROTHIXENE	ChEMBL	Phase 4 (approved)	TBXA2R
CHOLECALCIFEROL	ChEMBL	Phase 4 (approved)	TBXA2R
CICLOPIROX	ChEMBL	Phase 4 (approved)	TBXA2R
CISAPRIDE	ChEMBL	Phase 4 (approved)	TBXA2R
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	TBXA2R