General
Preferred name
DINOPROSTONE
Synonyms
Prostaglandin E2 ()
PGE2 ()
Prostaglandin E2 (PGE2) ()
Dinoprostone,Prepidil ()
[3H]PGE2 ()
Prostin E2 ()
Minprostin e2 ()
Dinoprostona ()
Enzaprost e ()
Propess ()
Dinoprostone beta-Cyclodextrin Clathrate ()
Prepidil ()
Cervidil ()
NSC-165560 ()
U-12,062 ()
Prostaglandin e2 ()
U-12062 ()
NSC-196514 ()
Prostaglandin E2-d4 ()
Prostaglandin E2 MaxSpec? Standard ()
Prostaglandin E2-d4 MaxSpec? Standard ()
Prostaglandin E2-d9 ()
P&D ID
PD009643
CAS
363-24-6
34210-10-1
1356347-42-6
Tags
available
drug
Approved by
FDA
PMDA
First approval
1977
Drug indication
Medical abortion
Prostaglandin
Oxytocic
Drug Status
withdrawn
approved
Max Phase
4.0
Structure
PD009643
DINOPROSTONE
approved
RO5
MW
352.22
HBA
4
HBD
3
RB
12
LOGP
3.25
147
32
0
29
Structure formats
SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
InChI
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChIkey
XEYBRNLFEZDVAW-ARSRFYASSA-N
MOL
DINOPROSTONE RDKit 2D 25 25 0 0 0 0 0 0 0 0999 V2000 10.2760 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5260 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0260 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2760 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7760 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0260 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7760 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5260 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2458 -1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 -2.6401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1459 -3.7548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3177 -5.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7849 -5.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2484 -6.9199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7156 -7.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1791 -8.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1755 -9.7730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6464 -8.9702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 2 0 10 9 1 6 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 1 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 16 10 1 0 M END > <ID> PD009643 > <Name> DINOPROSTONE
Description
(extracted from source data)
DESCRIPTION High affinity D1-like antagonist (Tocris Bioactive Compound Library)
DESCRIPTION Major endogenous prostanoid (Tocriscreen Total)
DESCRIPTION Prostaglandin E2 is a naturally occurring COX product used as a medication in labor induction, bleeding after delivery, and termination of pregnancy. It directly targets muscle stem cells (MuSCs) via EP4 receptor, resulting in MuSC expansion. (BOC Sciences Bioactive Compounds)
Protein targets
29
8.89
8.66
PTGER3 Prostaglandin E2 receptor EP3 subtype agonist BIOCHEM 6.2x
2
17
8.1
9.15
PTGER4 Prostaglandin E2 receptor EP4 subtype agonist CELL-BASED 3.1x
2
26
8
TSHR Thyrotropin receptor
2
1
7.8
8.36
PTGER2 Prostaglandin E2 receptor EP2 subtype agonist
2
24
7.75
8.24
PTGER1 Prostaglandin E2 receptor EP1 subtype agonist
2
14
6.75
PTGDR Prostaglandin D2 receptor agonist
2
4
6.65
6.6
PTGFR Prostaglandin F2-alpha receptor agonist
2
5
6.58
6.46
PTGIR Prostacyclin receptor
3
2
6.51
HPGDS Hematopoietic prostaglandin D synthase
2
1
6.3
CATSPER2 Cation channel sperm-associated protein 2 activator
1
1
6.3
CATSPER4 Cation channel sperm-associated protein 4 activator
1
1
6.3
CATSPER1 Cation channel sperm-associated protein 1 activator
1
1
6.3
CATSPER3 Cation channel sperm-associated protein 3 activator
1
1
6.11
NR1I2 Nuclear receptor subfamily 1 group I member 2
2
1
5.75
MAPK1 Mitogen-activated protein kinase 1
62
1
5.47
SLC22A6 Solute carrier family 22 member 6
1
1
5.35
PGR Progesterone receptor
5
1
5.3
PTGDR2 Prostaglandin D2 receptor 2 agonist
2
2
4.96
PDE4D 3',5'-cyclic-AMP phosphodiesterase 4D
3
1
4.82
PTGS1 Prostaglandin G/H synthase 1
2
1
4.74
SLC22A20 Solute carrier family 22 member 20
0
1
4.66
OPRK1 Kappa-type opioid receptor
3
1
4.64
AR Androgen receptor
6
1
4.64
ESR1 Estrogen receptor
15
1
4.55
HPGD 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
4
1
4.5
TBXA2R Thromboxane A2 receptor agonist
4
2
4.4
Cruzipain
0
1
SLCO2A1 Solute carrier organic anion transporter family member 2A1 binding agent
2
0
PTGER1,PTGER... Prostaglandin E2 receptor agonist
0
0
Target pathways
100
Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3
R-HSA-5625886
AR
Activation of the AP-1 family of transcription factors
R-HSA-450341
MAPK1
Advanced glycosylation endproduct receptor signaling
R-HSA-879415
MAPK1
Biosynthesis of D-series resolvins
R-HSA-9018676
HPGD
Biosynthesis of E-series 18(S)-resolvins
R-HSA-9018896
HPGD
Biosynthesis of Lipoxins (LX)
R-HSA-2142700
HPGD
Constitutive Signaling by Aberrant PI3K in Cancer
R-HSA-2219530
ESR1
COX reactions
R-HSA-140180
PTGS1
DARPP-32 events
R-HSA-180024
PDE4D
Defective SLCO2A1 causes primary, autosomal recessive hypertrophic osteoarthropathy 2 (PHOAR2)
R-HSA-5619095
SLCO2A1
Downregulation of SMAD2/3:SMAD4 transcriptional activity
R-HSA-2173795
MAPK1
ERK/MAPK targets
R-HSA-198753
MAPK1
ERKs are inactivated
R-HSA-202670
MAPK1
ESR-mediated signaling
R-HSA-8939211
MAPK1
ESR1
Estrogen-dependent gene expression
R-HSA-9018519
PGR
ESR1
Estrogen-dependent nuclear events downstream of ESR-membrane signaling
R-HSA-9634638
MAPK1
Estrogen-stimulated signaling through PRKCZ
R-HSA-9634635
MAPK1
Extra-nuclear estrogen signaling
R-HSA-9009391
ESR1
FCERI mediated MAPK activation
R-HSA-2871796
MAPK1
FCGR3A-mediated phagocytosis
R-HSA-9664422
MAPK1
Frs2-mediated activation
R-HSA-170968
MAPK1
G alpha (12/13) signalling events
R-HSA-416482
TBXA2R
G alpha (i) signalling events
R-HSA-418594
PTGER3
OPRK1
PTGDR2
G alpha (q) signalling events
R-HSA-416476
PTGER1
TBXA2R
PTGFR
G alpha (s) signalling events
R-HSA-418555
PDE4D
PTGIR
PTGER4
TSHR
PTGER2
PTGDR
Gastrin-CREB signalling pathway via PKC and MAPK
R-HSA-881907
MAPK1
Glutathione conjugation
R-HSA-156590
HPGDS
Golgi Cisternae Pericentriolar Stack Reorganization
R-HSA-162658
MAPK1
Growth hormone receptor signaling
R-HSA-982772
MAPK1
Hormone ligand-binding receptors
R-HSA-375281
TSHR
HSP90 chaperone cycle for steroid hormone receptors (SHR) in the presence of ligand
R-HSA-3371497
AR
PGR
IFNG signaling activates MAPKs
R-HSA-9732724
MAPK1
Interferon gamma signaling
R-HSA-877300
MAPK1
MAP2K and MAPK activation
R-HSA-5674135
MAPK1
MAPK1 (ERK2) activation
R-HSA-112411
MAPK1
MECP2 regulates neuronal receptors and channels
R-HSA-9022699
OPRK1
Mitochondrial unfolded protein response (UPRmt)
R-HSA-9841251
ESR1
NCAM signaling for neurite out-growth
R-HSA-375165
MAPK1
Negative feedback regulation of MAPK pathway
R-HSA-5674499
MAPK1
Negative regulation of FGFR1 signaling
R-HSA-5654726
MAPK1
Negative regulation of FGFR2 signaling
R-HSA-5654727
MAPK1
Negative regulation of FGFR3 signaling
R-HSA-5654732
MAPK1
Negative regulation of FGFR4 signaling
R-HSA-5654733
MAPK1
Negative regulation of MAPK pathway
R-HSA-5675221
MAPK1
Neutrophil degranulation
R-HSA-6798695
MAPK1
NPAS4 regulates expression of target genes
R-HSA-9768919
MAPK1
Nuclear events stimulated by ALK signaling in cancer
R-HSA-9725371
MAPK1
Nuclear Receptor transcription pathway
R-HSA-383280
AR
NR1I2
PGR
ESR1
Nuclear signaling by ERBB4
R-HSA-1251985
PGR
ESR1
Oncogene Induced Senescence
R-HSA-2559585
MAPK1
Organic anion transport
R-HSA-561048
SLC22A6
Ovarian tumor domain proteases
R-HSA-5689896
ESR1
Oxidative Stress Induced Senescence
R-HSA-2559580
MAPK1
Paradoxical activation of RAF signaling by kinase inactive BRAF
R-HSA-6802955
MAPK1
Peptide ligand-binding receptors
R-HSA-375276
OPRK1
phospho-PLA2 pathway
R-HSA-111995
MAPK1
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling
R-HSA-6811558
MAPK1
ESR1
PIP3 activates AKT signaling
R-HSA-1257604
ESR1
Prostacyclin signalling through prostacyclin receptor
R-HSA-392851
PTGIR
Prostanoid ligand receptors
R-HSA-391908
PTGER3
PTGIR
PTGER1
PTGER4
PTGDR2
TBXA2R
PTGER2
PTGDR
PTGFR
RAF-independent MAPK1/3 activation
R-HSA-112409
MAPK1
RAF/MAP kinase cascade
R-HSA-5673001
MAPK1
Recycling pathway of L1
R-HSA-437239
MAPK1
Regulation of actin dynamics for phagocytic cup formation
R-HSA-2029482
MAPK1
Regulation of HSF1-mediated heat shock response
R-HSA-3371453
MAPK1
Regulation of PTEN gene transcription
R-HSA-8943724
MAPK1
Regulation of RUNX2 expression and activity
R-HSA-8939902
ESR1
Regulation of the apoptosome activity
R-HSA-9627069
MAPK1
RHO GTPases Activate NADPH Oxidases
R-HSA-5668599
MAPK1
RHO GTPases Activate WASPs and WAVEs
R-HSA-5663213
MAPK1
RSK activation
R-HSA-444257
MAPK1
RUNX1 regulates estrogen receptor mediated transcription
R-HSA-8931987
ESR1
RUNX1 regulates transcription of genes involved in WNT signaling
R-HSA-8939256
ESR1
RUNX2 regulates osteoblast differentiation
R-HSA-8940973
AR
MAPK1
Senescence-Associated Secretory Phenotype (SASP)
R-HSA-2559582
MAPK1
Signal attenuation
R-HSA-74749
MAPK1
Signal transduction by L1
R-HSA-445144
MAPK1
Signaling by Activin
R-HSA-1502540
MAPK1
Signaling by BRAF and RAF1 fusions
R-HSA-6802952
MAPK1
Signaling by high-kinase activity BRAF mutants
R-HSA-6802948
MAPK1
Signaling by LTK in cancer
R-HSA-9842640
MAPK1
Signaling by MAP2K mutants
R-HSA-9652169
MAPK1
Signaling by MAPK mutants
R-HSA-9652817
MAPK1
Signaling by moderate kinase activity BRAF mutants
R-HSA-6802946
MAPK1
Signaling by NODAL
R-HSA-1181150
MAPK1
Signaling by RAF1 mutants
R-HSA-9656223
MAPK1
Signaling downstream of RAS mutants
R-HSA-9649948
MAPK1
SMAD2/SMAD3:SMAD4 heterotrimer regulates transcription
R-HSA-2173796
MAPK1
Sperm Motility And Taxes
R-HSA-1300642
CATSPER4
CATSPER3
CATSPER1
CATSPER2
Spry regulation of FGF signaling
R-HSA-1295596
MAPK1
SUMOylation of intracellular receptors
R-HSA-4090294
AR
NR1I2
PGR
ESR1
Suppression of apoptosis
R-HSA-9635465
MAPK1
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)
R-HSA-2162123
PTGS1
HPGDS
HPGD
TFAP2 (AP-2) family regulates transcription of growth factors and their receptors
R-HSA-8866910
ESR1
Thrombin signalling through proteinase activated receptors (PARs)
R-HSA-456926
MAPK1
Thromboxane signalling through TP receptor
R-HSA-428930
TBXA2R
Transcriptional and post-translational regulation of MITF-M expression and activity
R-HSA-9856649
MAPK1
Transport of organic anions
R-HSA-879518
SLCO2A1
Turbulent (oscillatory, disturbed) flow shear stress activates signaling by PIEZO1 and integrins in endothelial cells
R-HSA-9860927
PDE4D
Ub-specific processing proteases
R-HSA-5689880
AR
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PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease: Purified N370S Glucocerebrosidase. (Class of assay: confirmatory) [Related pubchem assays: 2101 ] AID 2597
Cell lines
1
4.2
K562
Organisms
0
Compound Sets
32
AdooQ Bioactive Compound Library
A11903
BOC Sciences Bioactive Compounds
prostaglandin-e2-cas-363-24-6-286161
Cayman Chemical Bioactives
10581
10007273
314010
10007211
14010
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL548
ChEMBL Drugs
CHEMBL548
Concise Guide to Pharmacology 2017/18
1883
1916
Concise Guide to Pharmacology 2019/20
1883
1916
Concise Guide to Pharmacology 2021/22
1883
1916
Concise Guide to Pharmacology 2023/24
1883
1916
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00917
DrugBank Approved Drugs
DB00917
DrugCentral
913
DrugCentral Approved Drugs
913
DrugMAP
DMTYOPD
DrugMAP Approved Drugs
DMTYOPD
EU-OPENSCREEN Bioactive Compound Library
EOS101721
Guide to Pharmacology
1883
1916
JUMP-Target 1 Compound Set
5280360
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL548
MedChem Express Bioactive Compound Library
HY-101952
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
prostaglandin-e2-cervidil
TargetMol Bioactive Compound Library
T5014
Tocris Bioactive Compound Library
2296
Tocriscreen Total
Withdrawn 2.0
w157
ZINC Tool Compounds
ZINC000003830713
Available from
10
AdooQ Bioactive Compound Library
A11903
BOC Sciences Bioactive Compounds
prostaglandin-e2-cas-363-24-6-286161
Cayman Chemical Bioactives
10581
14010
314010
10007211
10007273
Mcule
MCULE-8934660328
MCULE-3259881885
MedChem Express Bioactive Compound Library
HY-101952
MolPort
MolPort-003-939-184
Molport-003-939-184
Selleckchem Bioactive Compound Library
prostaglandin-e2-cervidil
TargetMol Bioactive Compound Library
T5014
Tocris Bioactive Compound Library
2296
Tocriscreen Total
External IDs
75
ChEMBL CHEMBL548
GtoPdb 1916 1883
PubChem 156593936 5283031 5280360 66630004
ZINC ZINC000003830713
ACToR 363-24-6
BindingDB 35847
Brenda 131299 55673 121883 16018 2700 153411 195152 154396 913 138728 229822 229821 158240 7272 179316
CCDC PROGLE
ChEBI 180942 15551
ChemicalBook CB8461799
ChemSpider 29342017 4446158 4444059
ClinicalTrials.gov PROSTIN E2 CERVIDIL PROSTAGLANDIN E2 PREPIDIL DINOPROSTONE PROPESS
COCONUT CNP0410482.1
CompTox DTXSID4022947
DailyMed DINOPROSTONE
DrugBank DB00917
DrugCentral 913
eMolecules 17497545 531175
FDA SRS K7Q1JQR04M
GSRS 355f095b-4fa8-4...
HMDB HMDB01220 HMDB0001220
IBM NIH 75BC2CA7C6F4C78...
KEGG C00584
LINCS LSM-42919
LipidMaps LMFA03010008 LMFA03010003
Mcule MCULE-8934660328 MCULE-3259881885
MetaboLights MTBLC15551
MolPort MolPort-003-939-184 Molport-003-939-184
Nikkaji J1.950.231G J9.243F
NMRShiftDB 60021031
PDB P2E
PharmGKB PA449345
PubChem DOTF 99431525
PubChem TPS 14900948 14778621
Reactome 29342017
RxNorm PREPIDIL PROSTIN E2 DINOPROSTONE CERVIDIL
Selleck prostaglandin-e...
SureChEMBL SCHEMBL25533 SCHEMBL239769
Properties
(calculated by RDKit )
Molecular Weight
352.22
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
3
Rotatable Bonds
12
Ring Count
1
Aromatic Ring Count
0
cLogP
3.25
TPSA
94.83
Fraction CSP3
0.7
Chiral centers
4.0
Largest ring
5.0
QED
0.37
Structural alerts
0
No structural alerts detected
Custom attributes
(extracted from source data)
MOA
prostaglandin receptor agonist
Prostaglandin Receptor
Endogenous Metabolite
Agonist
prostanoid receptor agonist
Target
Prostaglandin E2 receptor
EP2?Receptor
Human Endogenous Metabolite
CATSPER1, CATSPER2, CATSPER3, CATSPER4, PTGDR, PTGDR2, PTGER1, PTGER2, PTGER3, PTGER4, PTGFR, TBXA2R
CATSPER4
Organoid
PGES,Prostaglandin Receptor
Pathway
GPCR/G protein
Metabolism
Metabolic Enzyme/Protease
Stem Cell/Wnt
Primary Target
Prostanoid Receptors
Member status
member
ATC
G02AD02
Toxicity type
muscular
Therapeutic Class
Prostaglandins
Solubility
Soluble in DMSO.
Source data