Misoprostol
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Also known as CytotecMisoprostol component of arthrotecMysodelleSC-29333TopogyneSID11532984SID26755780SID26755781SID144205563
Summary
Misoprostol (CHEMBL606) is an approved small molecule (ATC G02AD06) targeting PTGER2, PTGER3, and PTGER4; indicated across 26 conditions including peptic ulcer disease and gastroesophageal reflux disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: G02AD06 (+1 more)
- Targets: 3 (PTGER2, PTGER3, PTGER4)
- Indications: 26 conditions
- Clinical trials: 384
- Chemistry: 382.5 Da · C22H38O5
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL606 |
| Name | Misoprostol |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 5282381 |
| ATC | G02AD06, A02BB01 |
| Molecular formula | C22H38O5 |
| Molecular weight | 382.5 |
| InChIKey | OJLOPKGSLYJEMD-URPKTTJQSA-N |
SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
IUPAC name: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
Also known as: Cytotec, Misoprostol, Misoprostol component of arthrotec, Mysodelle, SC-29333, Topogyne, SID11532984, SID26755780, SID26755781, MISOPROSTOL, misoprostol, SID144205563
Patent coverage: 4,083 distinct patent families (15,994 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 |
|---|---|---|---|---|---|
| PTGER2 | EP2 receptor | Full agonist | 5 | 0.1% | P43116 |
| PTGER3 | EP3 receptor | Full agonist | 6.5 | 2.6% | P43115 |
| PTGER4 | EP4 receptor | Full agonist | 5.3 | 0.5% | P35408 |
Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Microtubule-associated protein tau, Nuclear receptor ROR-gamma, Prelamin-A/C, Progesterone receptor, DNA polymerase beta, Cruzipain, Aldehyde dehydrogenase 1A1, Neuropeptide S receptor.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| LMNA | 6.1 | Potency | 794.3 | nM | CHEMBL_ACT_3648313 |
Target pathways
Aggregated over 3 target gene(s): PTGER2, PTGER3, PTGER4.
Top Reactome pathways
3 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Prostanoid ligand receptors | 3 | PTGER2, PTGER3, PTGER4 |
| G alpha (s) signalling events | 2 | PTGER2, PTGER4 |
| G alpha (i) signalling events | 1 | PTGER3 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| inflammatory response | 3 |
| G protein-coupled receptor signaling pathway | 3 |
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 3 |
| positive regulation of cytosolic calcium ion concentration | 3 |
| signal transduction | 3 |
| cellular response to prostaglandin E stimulus | 2 |
| response to nematode | 1 |
| response to lipopolysaccharide | 1 |
| response to progesterone | 1 |
| regulation of cell population proliferation | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| cell death | 1 |
| intestine smooth muscle contraction | 1 |
| positive regulation of fever generation | 1 |
| negative regulation of gastric acid secretion | 1 |
Indications & clinical
Indications
26 indications (7 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 |
|---|---|---|---|
| peptic ulcer disease | 4 | MONDO:0004247 | HP:0004398 |
| gastroesophageal reflux disease | 4 | MONDO:0007186 | EFO:0003948 |
| gastric ulcer | 4 | MONDO:0001126 | EFO:0009454 |
| duodenal ulcer | 4 | MONDO:0005412 | EFO:0004607 |
| osteoarthritis | 4 | MONDO:0005178 | MONDO:0005178 |
| uterine corpus leiomyoma | 3 | MONDO:0007886 | EFO:0000731 |
| obesity disorder | 3 | MONDO:0011122 | EFO:0001073 |
| preeclampsia | 3 | MONDO:0005081 | EFO:0000668 |
| ankylosing spondylitis | 3 | MONDO:0005306 | EFO:0003898 |
| uterine disorder | 3 | MONDO:0002654 | MONDO:0000931 |
| leiomyoma | 3 | MONDO:0001572 | MONDO:0001572 |
| benign muscle neoplasm | 3 | MONDO:0003061 | MONDO:0003061 |
| Clostridium infectious disease | 2 | MONDO:0024388 | EFO:1000874 |
| metabolic dysfunction-associated steatohepatitis | 2 | MONDO:0007027 | EFO:1001249 |
12 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 384.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 136 |
| PHASE4 | 103 |
| PHASE3 | 64 |
| PHASE2 | 36 |
| PHASE2/PHASE3 | 22 |
| EARLY_PHASE1 | 11 |
| PHASE1 | 10 |
| PHASE1/PHASE2 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03675672 | PHASE4 | RECRUITING | Prevention of Recurrent Ulcer Bleeding in Patients With Idiopathic Gastroduodenal Ulcer |
| NCT06049745 | PHASE4 | NOT_YET_RECRUITING | Use of Misoprostol in Hysteroscopic Myomectomy |
| NCT06946914 | PHASE4 | RECRUITING | Misoprostol Before Caesarean Section |
| NCT07286188 | PHASE4 | RECRUITING | Effect of Misoprostol on Fluid Deficit Volume in Hysteroscopic Myomectomy |
| NCT00129506 | PHASE4 | COMPLETED | Comparing Methotrexate Followed by Misoprostol to Misoprostol Alone for Early Abortion |
| NCT00177372 | PHASE4 | COMPLETED | Mifepristone and Misoprostol for Fetal Demise |
| NCT00256009 | PHASE4 | UNKNOWN | Treatment of Late Abortion: Evacuatio Uteri or Conservative Treatment |
| NCT00269568 | PHASE4 | COMPLETED | Mifepristone at Same Time Multicenter Study |
| NCT00324519 | PHASE4 | COMPLETED | Randomized Trial Comparing Misoprostol and Foley Bulb for Pregnancy Termination in the Second Trimester |
| NCT00355303 | PHASE4 | COMPLETED | Comparison of Misoprostol and Prostaglandin E2 (PGE2) Gel for Induction of Labour in Premature Rupture of Membranes at Term |
| NCT00355966 | PHASE4 | COMPLETED | Comparison of Misoprostol and PGE2 Gel for Induction of Labour in Women With Premature Rupture of Membranes at Term |
| NCT00383942 | PHASE4 | TERMINATED | Ripening Interventions: Prostaglandins vs EASI Catheter |
| NCT00393198 | PHASE4 | COMPLETED | Bleeding Pattern and User Satisfaction During Second Consecutive MIRENA® in Contraception and Treatment of Menorrhagia |
| NCT00401440 | PHASE4 | COMPLETED | Comparison of Two Regimens of Misoprostol for Second Trimester Medical Termination of Pregnancy |
| NCT00695331 | PHASE4 | UNKNOWN | Efficacy and Safety Study of Titrated Oral Misoprostol Solution for Labor Augmentation |
| NCT00886860 | PHASE4 | COMPLETED | The Comparison of Efficacy for Cervical Ripening in Labor Induction Between Titrated and Conventional Oral Misoprostol |
| NCT00906347 | PHASE4 | COMPLETED | A Trial of Oral Misoprostol for Labor Augmentation |
| NCT00997347 | PHASE4 | COMPLETED | The Extended Gestational Age Medical Abortion Study |
| NCT01113229 | PHASE4 | TERMINATED | Combined Use of Oxytocin and Misoprostol in the Prevention of Post Partum Haemorrhage |
| NCT01156688 | PHASE4 | COMPLETED | A Prospective Randomized Comparison Trial on the Use of Mifepristone With Sublingual or Buccal Misoprostol for Medical Abortions of Less Than 9 Weeks Gestation |
| NCT01231126 | PHASE4 | COMPLETED | Evaluation the Blood Loss in Pregnancies With Misoprostol-induced Labour |
| NCT01406392 | PHASE4 | COMPLETED | Sublingual Misoprostol for Induction of Labor |
| NCT01519765 | PHASE4 | TERMINATED | Buccal Versus Vaginal Misoprostol for Third Trimester Induction of Labor |
| NCT01620814 | PHASE4 | UNKNOWN | Intravaginal Misoprostol Versus Dinoprostone Before Diagnostik Hysteroscopy |
| NCT01700478 | PHASE4 | COMPLETED | Study of the Use of Misoprostol to Decrease Bleeding During a Myomectomy |
| NCT01733329 | PHASE4 | COMPLETED | Buccal Misoprostol During Cesarean Section for Preventing Postpartum Hemorrhage |
| NCT01754649 | PHASE4 | COMPLETED | Use of Misoprostol in Case of Insertion Failure of Intrauterine Contraceptives |
| NCT01768299 | PHASE4 | COMPLETED | Medical Abortion With Mifepristone + Misoprostol (13 - 22 Weeks) |
| NCT01798017 | PHASE4 | COMPLETED | Introducing Mifepristone-Misoprostol for Menstrual Regulation in Public Sector Facilities in Bangladesh |
| NCT01856985 | PHASE4 | COMPLETED | Acceptability of an Out-patient Regimen of Medical Abortion With Mifepristone and 800 Mcg Misoprostol Administered at 78-84 Days Gestation |
| NCT01931410 | PHASE4 | COMPLETED | The Effect of Rectal and Sublingual Misoprostol Administration in Postpartum or Intrapartum Haemorrhage at Elective Caesarean Delivery: a Randomized Controlled Trial |
| NCT02209545 | PHASE4 | TERMINATED | Misoprostol for Reduction of Blood Loss During Fibroid Surgery |
| NCT02226588 | PHASE4 | COMPLETED | Comparison of Primary and Secondary Prevention of Postpartum Hemorrhage at the Community Level in Egypt |
| NCT02277041 | PHASE4 | UNKNOWN | Carbetocin Versus Misoprostol in Cases With Placenta Previa After C.S. |
| NCT02277067 | PHASE4 | UNKNOWN | Carbetocin Versus Misoprostol in High Risk Patients for Postpartum Hemorrhage After C.S. |
| NCT02342002 | PHASE4 | TERMINATED | Mifepristone and Misoprostol Versus Misoprostol Alone for Missed Abortion: A Randomized-controlled Trial |
| NCT02412618 | PHASE4 | COMPLETED | Same-Day Mifepristone-Misoprostol Compared to Misoprostol Only for Surgical Abortion Cervical Preparation |
| NCT02474433 | PHASE4 | UNKNOWN | Same-day Cervical Preparation With Misoprostol Before Hysteroscopy |
| NCT02480543 | PHASE4 | UNKNOWN | Different Routes of Misoprostol Prior to First Trimester Surgical Abortion |
| NCT02488642 | PHASE4 | COMPLETED | Medical Management of Late Intrauterine Death. |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
24 molecules share ≥1 primary target. Top 24 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Dinoprost | ChEMBL + PubChem | Phase 4 (approved) | PTGER2, PTGER3, PTGER4 |
| DINOPROSTONE | ChEMBL + PubChem | Phase 4 (approved) | PTGER2, PTGER3, PTGER4 |
| OMIDENEPAG ISOPROPYL | ChEMBL + PubChem | Phase 4 (approved) | PTGER2, PTGER3, PTGER4 |
| RALINEPAG | ChEMBL | Phase 3 | PTGER2, PTGER3, PTGER4 |
| Grapiprant | ChEMBL + PubChem | Phase 2 (approved) | PTGER2, PTGER3, PTGER4 |
| OMIDENEPAG | ChEMBL + PubChem | Phase 2 (approved) | PTGER2, PTGER3, PTGER4 |
| ILOPROST | ChEMBL + PubChem | Phase 4 (approved) | PTGER2, PTGER3 |
| LAROPIPRANT | ChEMBL | Phase 4 (approved) | PTGER2, PTGER3 |
| CLOPROSTENOL | ChEMBL | Phase 2 | PTGER2, PTGER3 |
| PALUPIPRANT | ChEMBL | Phase 2 | PTGER2, PTGER4 |
| Belzutifan | PubChem | Approved | PTGER2, PTGER3 |
| TREPROSTINIL | ChEMBL | Phase 4 (approved) | PTGER2 |
| SEPETAPROST | ChEMBL | Phase 3 | PTGER3 |
| SETIPIPRANT | ChEMBL | Phase 3 | PTGER2 |
| BGC-20-1531 | ChEMBL | Phase 2 | PTGER4 |
| BGC-20-1531 FREE BASE | ChEMBL | Phase 2 | PTGER4 |
| BMS-986310 | ChEMBL | Phase 2 | PTGER4 |
| BUTAPROST | ChEMBL | Phase 2 | PTGER2 |
| 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 |
| Alprostadil | PubChem | Approved | PTGER2 |
Related Atlas pages
- Genes: PTGER2, PTGER3, PTGER4
- Diseases: peptic ulcer disease, gastroesophageal reflux disease, gastric ulcer, duodenal ulcer, osteoarthritis, uterine corpus leiomyoma, obesity disorder, preeclampsia, ankylosing spondylitis, uterine disorder, leiomyoma, benign muscle neoplasm
- Drugs: Dinoprost, Dinoprostone, Omidenepag Isopropyl, Ralinepag, Iloprost, Laropiprant, Belzutifan, Treprostinil, Sepetaprost, Setipiprant, Alprostadil