Dinoprost
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Also known as Pgf2.alpha.Pgf2aPgf2alphaProsmonProstaglandin f2.alpha.Prostaglandin f2alphaU-14,583U-14583SID29216066Prostaglandin F2aSID144205330PROSTAGLANDIN F2 ALPHAProstaglandin F2?
Summary
Dinoprost (CHEMBL815) is an approved small molecule (ATC G02AD01) targeting PTGDR, PTGDR2, and PTGER1.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: G02AD01
- Targets: 8 (PTGDR, PTGDR2, PTGER1…)
- Clinical trials: 2
- Chemistry: 354.5 Da · C20H34O5
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL815 |
| Name | Dinoprost |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 5280363 |
| ChEBI | CHEBI:15553 |
| ATC | G02AD01 |
| Molecular formula | C20H34O5 |
| Molecular weight | 354.5 |
| InChIKey | PXGPLTODNUVGFL-YNNPMVKQSA-N |
SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
IUPAC name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
ChEBI definition: A prostaglandins Fα that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.
Other ChEBI roles (chemical / environmental): human metabolite, mouse metabolite.
Also known as: Dinoprost, Pgf2.alpha., Pgf2a, Pgf2alpha, Prosmon, Prostaglandin f2.alpha., Prostaglandin f2alpha, U-14,583, U-14583, SID29216066, Prostaglandin F2a, Prostaglandin F2alpha
Parent form; salt/anhydrous children: CHEMBL1200896
Patent coverage: 1,264 distinct patent families (3,118 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 | 6.4 | 0.4% | Q13258 |
| PTGDR2 | DP2 receptor | Full agonist | 6.4 | 0% | Q9Y5Y4 |
| PTGER1 | EP1 receptor | Full agonist | 6.3 | 0.4% | P34995 |
| PTGER2 | EP2 receptor | Full agonist | 6 | 0.1% | P43116 |
| PTGER3 | EP3 receptor | Full agonist | 7.42 | 2.6% | P43115 |
| PTGER4 | EP4 receptor | Full agonist | 6.05 | 0.5% | P35408 |
| PTGFR | FP receptor | Full agonist | 8.5 | 0% | P43088 |
| TBXA2R | TP receptor | Full agonist | 5.1 | 0.2% | P21731 |
Broader ChEMBL bioactivity targets: 13 (assay-derived). Sample: Prelamin-A/C, Prostaglandin E2 receptor EP1 subtype, Prostaglandin E2 receptor EP4 subtype, Prostaglandin F2-alpha receptor, Thromboxane A2 receptor, Solute carrier organic anion transporter family member 2A1, Solute carrier organic anion transporter family member 2B1, Solute carrier organic anion transporter family member 2A1, Solute carrier organic anion transporter family member 2A1, Prostaglandin E2 receptor EP3 subtype.
Bioactivity
ChEMBL activities: 28 potent at pChembl ≥ 5 of 29 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PTGFR | 8.6 | IC50 | 2.5 | nM | CHEMBL_ACT_839809 |
| PTGFR | 8.52 | IC50 | 3 | nM | CHEMBL_ACT_468795 |
| PTGFR | 8.15 | IC50 | 7 | nM | CHEMBL_ACT_211057 |
| P43117 | 7.9 | EC50 | 12.59 | nM | CHEMBL_ACT_12660304 |
| SLCO2A1 | 7.64 | Ki | 23 | nM | CHEMBL_ACT_11002236 |
| PTGFR | 7.61 | EC50 | 24.5 | nM | CHEMBL_ACT_1444489 |
| P43117 | 7.61 | EC50 | 24.5 | nM | CHEMBL_ACT_2386963 |
| PTGFR | 7.37 | IC50 | 43 | nM | CHEMBL_ACT_173543 |
| Q00910 | 7.35 | Ki | 45 | nM | CHEMBL_ACT_11002245 |
| PTGFR | 7.1 | EC50 | 79 | nM | CHEMBL_ACT_839810 |
| Q9EPT5 | 6.98 | Ki | 104 | nM | CHEMBL_ACT_11002255 |
| PTGER3 | 6.96 | IC50 | 110 | nM | CHEMBL_ACT_468798 |
| PTGFR | 6.92 | Ki | 119 | nM | CHEMBL_ACT_857585 |
| P37289 | 6.89 | Ki | 129 | nM | CHEMBL_ACT_1444488 |
| P37289 | 6.89 | Ki | 130 | nM | CHEMBL_ACT_2386955 |
| P37289 | 6.85 | IC50 | 140 | nM | CHEMBL_ACT_173542 |
| PTGER1 | 6.66 | IC50 | 220 | nM | CHEMBL_ACT_468796 |
| Q9JHI3 | 6.54 | IC50 | 287 | nM | CHEMBL_ACT_11000851 |
| PTGER3 | 6.49 | IC50 | 322 | nM | CHEMBL_ACT_211060 |
| PTGER1 | 6.42 | IC50 | 380 | nM | CHEMBL_ACT_211058 |
| PTGER1 | 6.22 | EC50 | 600 | nM | CHEMBL_ACT_839812 |
| TBXA2R | 5.85 | EC50 | 1400 | nM | CHEMBL_ACT_839811 |
| PTGER3 | 5.64 | EC50 | 2300 | nM | CHEMBL_ACT_839813 |
| TBXA2R | 5.56 | AC50 | 2760 | nM | CHEMBL_ACT_25211342 |
| PTGER4 | 5.38 | IC50 | 4200 | nM | CHEMBL_ACT_211061 |
| PTGER4 | 5.38 | IC50 | 4200 | nM | CHEMBL_ACT_468799 |
| PTGDR | 5.35 | IC50 | 4500 | nM | CHEMBL_ACT_211063 |
| PTGDR | 5.35 | IC50 | 4500 | nM | CHEMBL_ACT_468802 |
Target pathways
Aggregated over 8 target gene(s): PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R.
Top Reactome pathways
15 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Prostanoid ligand receptors | 8 | PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R |
| 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 |
| cellular response to prostaglandin D stimulus | 3 |
| immune response | 2 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 2 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 2 |
| response to prostaglandin E | 2 |
| cellular response to prostaglandin E stimulus | 2 |
| response to lipid | 2 |
| male sex determination | 1 |
| sleep | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 2.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01327118 | Not specified | COMPLETED | Prostaglandin F2alpha in a Human Headache Model |
| NCT01689311 | Not specified | COMPLETED | In Vitro Myometrial Contractions in Laboring and Non-laboring Women |
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.
314 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| dinoprostone | 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 |
| 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 |
| Alprostadil | PubChem | Approved | PTGDR, PTGER2 |
| Latanoprostene Bunod | PubChem | Approved | PTGFR, TBXA2R |
| 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 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | TBXA2R |
Related Atlas pages
- Genes: PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R
- Drugs: dinoprostone, Laropiprant, Ralinepag, Belzutifan, Iloprost, omidenepag isopropyl, Ramatroban, Treprostinil, Setipiprant, Indomethacin, Tafluprost, Selexipag, Sepetaprost, Timapiprant, Alprostadil, Latanoprostene Bunod, Clozapine, Desloratadine, Dihydroergotamine, Estradiol Valerate, Olanzapine, Pimavanserin, Pomalidomide, Regorafenib, Rifampin, Tegaserod, Acetylcholine, Amitriptyline, Amlodipine, Amsacrine, Aripiprazole, Astemizole, Axitinib, Beclomethasone Dipropionate, Benzbromarone, Benziodarone, Bexarotene, Bithionol, Bromocriptine, Bromodiphenhydramine, Cabozantinib, Candesartan Cilexetil, Cannabidiol, Cerivastatin, Chlormadinone, Chlorprothixene, Cholecalciferol, Ciclopirox, Cisapride, Clomipramine, Clotrimazole