Compound Detail

CHEMBL548

DINOPROSTONE

💊 Approved Drug

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💊 Approved Drug

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL548
Name	DINOPROSTONE
Phase	Approved
Structure Type	MOL
InChI Key	XEYBRNLFEZDVAW-ARSRFYASSA-N
Therapeutic	✓ Yes

Known Names

Cervidil Dinoprostona Dinoprostone Dinoprostone beta-cyclodextrin clathrate Enzaprost e Minprostin e2 NSC-165560 NSC-196514 Prepidil Propess Prostaglandin e2 Prostin e2 +2 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

352.5

MW (Da)

3.25

ALogP

HBA

HBD

94.8

PSA (Å²)

0.37

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1977
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Natural Product

USAN Stem	-prost-
USAN Year	1971

Extended Properties

Molecular Formula	C20H32O5
MW	352.47
Aromatic Rings	0
Heavy Atoms	25
NP-Likeness	2.03

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Prostaglandin E2 receptor agonist	AGONIST	Prostaglandin E2 receptor	✓	✓

Indications

Fetal Growth Retardation Myoma Pain Pregnancy Abortion, Incomplete

ATC Classification

G02AD02

dinoprostone

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: OTHER GYNECOLOGICALS

Activity Summary

Ki 34 meas. best 9.96

EC50 21 meas. best 10.7

IC50 21 meas. best 9.49

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin E2 receptor EP4 subtype CHEMBL1836	EC50	10.7	9.018	0.0	5
Prostaglandin E2 receptor EP4 subtype CHEMBL1836	Ki	9.96	9.2733	0.1	9
Prostaglandin E2 receptor EP2 subtype CHEMBL4909	EC50	9.7	8.71	0.2	2
Prostaglandin E2 receptor EP4 subtype CHEMBL1836	IC50	9.49	8.8663	0.3	8
Prostaglandin E2 receptor EP3 subtype CHEMBL3710	Ki	9.48	8.98	0.3	4
Prostaglandin E2 receptor EP4 subtype CHEMBL4086	EC50	9.15	8.805	0.7	2
Prostaglandin E2 receptor EP3 subtype CHEMBL3710	IC50	9.03	9.03	0.9	1
Prostaglandin E2 receptor EP2 subtype CHEMBL1881	Ki	8.99	8.3517	1.0	6
Prostaglandin E2 receptor EP1 subtype CHEMBL1811	IC50	8.96	8.96	1.1	1
Prostaglandin E2 receptor EP2 subtype CHEMBL1881	EC50	8.72	7.705	1.9	6
Prostaglandin E2 receptor EP4 subtype CHEMBL4086	IC50	8.68	8.68	2.1	1
Prostaglandin E2 receptor EP2 subtype CHEMBL1881	IC50	8.66	8.3567	2.2	6
Prostaglandin E2 receptor EP3 subtype CHEMBL3710	EC50	8.6	8.6	2.5	1
Prostaglandin E2 receptor EP4 subtype CHEMBL2489	Ki	8.51	8.51	3.1	2
Prostaglandin E2 receptor EP1 subtype CHEMBL1811	EC50	8.43	8.43	3.7	1
Prostaglandin E2 receptor EP3 subtype CHEMBL4336	Ki	8.3	8.3	5.0	2
Prostaglandin E2 receptor EP2 subtype CHEMBL4909	IC50	8.28	8.28	5.2	1
Prostaglandin E2 receptor EP1 subtype CHEMBL2181	Ki	8.22	8.22	6.0	2
Prostaglandin E2 receptor EP1 subtype CHEMBL1811	Ki	8.04	7.9433	9.1	3
Unchecked CHEMBL612545	IC50	7.76	7.76	17.3	1
Prostaglandin E2 receptor EP2 subtype CHEMBL2488	Ki	7.66	7.66	22.0	2
Unchecked CHEMBL612545	EC50	7.05	6.965	90.0	2
Prostaglandin F2-alpha receptor CHEMBL1987	EC50	6.6	6.6	250.0	1
Prostacyclin receptor CHEMBL1995	IC50	6.58	6.58	260.0	1
Prostacyclin receptor CHEMBL1995	EC50	6.46	6.46	347.0	1
Solute carrier family 22 member 6 CHEMBL5653	Ki	5.47	5.47	3388.4	2
Solute carrier family 22 member 20 CHEMBL5269	Ki	4.75	4.745	18000.0	2
K562 CHEMBL385	IC50	4.2	4.2	63000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	336.0	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin E2 receptor EP4 subtype	EC50	=	0.02	nM	10.7	Agonist activity at human EP4 receptor expressed in HEK293T/17 cells assessed as...	30964292
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.11	nM	9.96	Displacement of [3H]PGE2 from human recombinant EP4 receptor expressed in HEK293...	30964292
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.14	nM	9.85	Binding affinity to EP4 (unknown origin) assessed as inhibition constant	28849908
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.17	nM	9.77	Binding affinity to human prostanoid EP4 receptor by radioligand displacement as...	23466604
Prostaglandin E2 receptor EP2 subtype	EC50	=	0.2	nM	9.7	Agonist activity against rat EP2 receptor expressed in HEK293 cells assessed as ...	19250823
Prostaglandin E2 receptor EP4 subtype	IC50	=	0.32	nM	9.49	Inhibition of EP4 (unknown origin)	28849908
Prostaglandin E2 receptor EP3 subtype	Ki	=	0.33	nM	9.48	Displacement of [3H]PGE2 from human EP3 receptor expressed in HEK293 cells	17531488
Prostaglandin E2 receptor EP3 subtype	Ki	=	0.33	nM	9.48	Displacement of [3H]PGE2 from human EP3 receptor	18039575
Prostaglandin E2 receptor EP4 subtype	IC50	=	0.45	nM	9.35	Binding affinity to human prostanoid EP4 receptor by radioligand displacement as...	23466604
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.45	nM	9.35	Displacement of [3H]PGE2 from human recombinant prostanoid EP4 receptor in CHEM1...	23403082
Prostaglandin E2 receptor EP4 subtype	IC50	=	0.55	nM	9.26	Displacement of [3H]PGE2 from human recombinant EP4 receptor expressed in HEK293...	27876250
Prostaglandin E2 receptor EP4 subtype	EC50	=	0.583	nM	9.23	Agonist activity at human EP4 receptor expressed in HEK293T/17 cells assessed as...	30964292
Prostaglandin E2 receptor EP4 subtype	IC50	=	0.7	nM	9.15	Inhibitory activity against human EP4 receptor expressed in HEK293 ebna cells	12643927
Prostaglandin E2 receptor EP4 subtype	EC50	=	0.7	nM	9.15	Agonist activity against rat EP4 receptor expressed in HEK293 cells assessed as ...	19250823
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.79	nM	9.1	Displacement of [3H]PGE4 from human EP4 receptor	18039575
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.79	nM	9.1	Displacement of [3H]PGE2 from human EP4 receptor expressed in HEK293 cells	17531488
Prostaglandin E2 receptor EP4 subtype	Ki	=	0.79	nM	9.1	Binding affinity at human prostaglandin EP4 receptor	17931866
Prostaglandin E2 receptor EP3 subtype	IC50	=	0.94	nM	9.03	Binding affinity to EP3 receptor	20218623
Prostaglandin E2 receptor EP2 subtype	Ki	=	1.03	nM	8.99	Displacement of [3H]PGE2 from human recombinant EP2 receptor expressed in HEK293...	30964292
Prostaglandin E2 receptor EP1 subtype	IC50	=	1.1	nM	8.96	Binding affinity to EP1 receptor	20218623

Literature References

PubMed	DOI	Target Context	# Activities
11708917	10.1021/jm010264b	Rattus norvegicus	19
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
410931	10.1021/jm00221a036	No relevant target	11
7086833	10.1021/jm00347a003	Rattus norvegicus	10
19172146	10.1038/nchembio.147	Danio rerio	9
-	10.1039/C6MD00235H	Solute carrier organic anion transporter family member 2B1	7
189028	10.1021/jm00211a007	Unchecked	6
2666669	10.1021/jm00128a049	Rattus norvegicus	5
21595651	10.1111/j.1476-5381.2011.01495.x	Unchecked	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
17553798	10.1074/jbc.m703467200	Solute carrier family 22 member 20	3
23403082	10.1016/j.bmcl.2013.01.025	Prostaglandin E2 receptor EP4 subtype	3
6796685	10.1021/jm00143a018	Cavia porcellus	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
30964292	10.1021/acs.jmedchem.9b00336	Prostaglandin E2 receptor EP4 subtype	3
6827556	10.1021/jm00357a006	Canis familiaris	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
30964292	10.1021/acs.jmedchem.9b00336	Prostaglandin E2 receptor EP2 subtype	3
17553798	10.1074/jbc.m703467200	Solute carrier family 22 member 6	3
2769690	10.1021/jm00129a028	Rattus norvegicus	3

Data from ChEMBL 36 via Core Engine