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Compound Detail

CHEMBL815

DINOPROST
💊 Approved Drug
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💊 Approved Drug
CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL815
Name DINOPROST
Phase Approved
Structure Type MOL
InChI Key PXGPLTODNUVGFL-YNNPMVKQSA-N
Therapeutic ✓ Yes

Known Names

Dinoprost Pgf2.alpha. Pgf2a Pgf2alpha Prosmon Prostaglandin f2-alpha Prostaglandin f2.alpha. Prostaglandin f2alpha U-14,583 U-14583
14
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
10
Known Names

Molecular Properties

354.5
MW (Da)
3.04
ALogP
4
HBA
4
HBD
98.0
PSA (Ų)
0.32
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -prost
USAN Year 1971

Extended Properties

Molecular Formula C20H34O5
MW 354.49
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 1.94

ATC Classification

G02AD01
dinoprost
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: OTHER GYNECOLOGICALS

Activity Summary

IC50 14 meas. best 8.6
EC50 9 meas. best 8.17
Ki 6 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin F2-alpha receptor
CHEMBL1987
 IC50 8.6 8.16 2.5 4
Felis catus
CHEMBL612670
 EC50 8.17 8.17 6.7 1
Prostaglandin F2-alpha receptor
CHEMBL5000
 EC50 7.9 7.755 12.6 2
Unchecked
CHEMBL612545
 EC50 7.64 7.64 23.0 1
Solute carrier organic anion transporter family member 2A1
CHEMBL2073703
 Ki 7.64 7.64 23.0 1
Prostaglandin F2-alpha receptor
CHEMBL1987
 EC50 7.61 7.355 24.5 2
Solute carrier organic anion transporter family member 2A1
CHEMBL2073680
 Ki 7.35 7.35 45.0 1
Solute carrier organic anion transporter family member 2A1
CHEMBL2073699
 Ki 6.98 6.98 104.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
 IC50 6.96 6.725 110.0 2
Prostaglandin F2-alpha receptor
CHEMBL1987
 Ki 6.92 6.92 119.0 1
Prostaglandin F2-alpha receptor
CHEMBL4820
 Ki 6.89 6.89 129.0 2
Prostaglandin F2-alpha receptor
CHEMBL4820
 IC50 6.85 6.85 140.0 1
Prostaglandin E2 receptor EP1 subtype
CHEMBL1811
 IC50 6.66 6.54 220.0 2
Solute carrier organic anion transporter family member 2B1
CHEMBL2073698
 IC50 6.54 6.54 287.0 1
Prostaglandin E2 receptor EP1 subtype
CHEMBL1811
 EC50 6.22 6.22 600.0 1
Thromboxane A2 receptor
CHEMBL2069
 EC50 5.85 5.85 1400.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
 EC50 5.64 5.64 2300.0 1
Prostaglandin E2 receptor EP4 subtype
CHEMBL1836
 IC50 5.38 5.38 4200.0 2
Prostaglandin D2 receptor
CHEMBL4427
 IC50 5.35 5.35 4500.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin F2-alpha receptor IC50 = 2.5 nM 8.6 Displacement of [3H]PGF2-alpha from human FP-receptor expressed in CHO-KI cells 10915040
Prostaglandin F2-alpha receptor IC50 = 3.0 nM 8.52 In vitro binding at FP human prostaglandin receptor using [3H]PGF-2 alpha as rad... 11708917
Felis catus EC50 = 6.7 nM 8.17 Concentration giving half-maximal contraction of the cat iris sphincter muscle w... 7830272
Prostaglandin F2-alpha receptor IC50 = 7.0 nM 8.15 Affinity for human Prostanoid FP receptor expressed in COS-7 cells 10715159
Prostaglandin F2-alpha receptor EC50 = 12.59 nM 7.9 Agonist activity at FP receptor in mouse 3T3 fibroblast cells assessed as intrac... 23317571
Solute carrier organic anion transporter family member 2A1 Ki = 23.0 nM 7.64 TP_TRANSPORTER: inhibition of PGE2 uptake in PGT-expressing HeLa cells 10484490
Unchecked EC50 = 23.0 nM 7.64 Evaluated for its concentration at which 50% of maximal stimulation of phosphoin... 10978187
Prostaglandin F2-alpha receptor EC50 = 24.5 nM 7.61 Agonist activity at FP receptor in Swiss mouse 3T3 cells assessed as [3H]-IP acc... 19101156
Prostaglandin F2-alpha receptor EC50 = 24.5 nM 7.61 Efficacy for stimulation of prostanoid FP receptor-linked phosphoinositide turno... 15357985
Prostaglandin F2-alpha receptor IC50 = 43.0 nM 7.37 Binding potency towards Prostaglandin F2 alpha receptor (competitive binding) wi... 2909739
Solute carrier organic anion transporter family member 2A1 Ki = 45.0 nM 7.35 TP_TRANSPORTER: inhibition of PGE2 uptake in PGT-expressing HeLa cells 10484490
Prostaglandin F2-alpha receptor EC50 = 79.0 nM 7.1 Functional activity in RAT-1cells, transiently-transfected with human FP-recepto... 10915040
Solute carrier organic anion transporter family member 2A1 Ki = 104.0 nM 6.98 TP_TRANSPORTER: inhibition of PGE2 uptake in PGT-expressing HeLa cells 10484490
Prostaglandin E2 receptor EP3 subtype IC50 = 110.0 nM 6.96 In vitro binding at EP3 human prostaglandin receptor using [3H]PGE-2 as radiolig... 11708917
Prostaglandin F2-alpha receptor Ki = 119.0 nM 6.92 Inhibitory Binding constant (n=2) to Prostanoid FP receptor expressed in bovine ... 10978187
Prostaglandin F2-alpha receptor Ki = 129.0 nM 6.89 Binding affinity for Prostanoid FP receptor of bovine corpus luteum 15357985
Prostaglandin F2-alpha receptor Ki = 130.0 nM 6.89 Displacement of [3H]PGF2 alpha from FP receptor in bovine corpus luteum membrane 19101156
Prostaglandin F2-alpha receptor IC50 = 140.0 nM 6.85 Binding potency towards Prostaglandin F2 alpha receptor (competitive binding) wi... 2909739
Prostaglandin E2 receptor EP1 subtype IC50 = 220.0 nM 6.66 In vitro binding at EP1 human prostaglandin receptor using [3H]PGE-2 as radiolig... 11708917
Solute carrier organic anion transporter family member 2B1 IC50 = 287.0 nM 6.54 TP_TRANSPORTER: inhibition of PGD2 uptake in Xenopus laevis oocytes 10973807

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 U2OS 9
- 10.6019/CHEMBL4689842 Fibroblast 6
6876076 10.1021/jm00362a001 Rattus norvegicus 4
19101156 10.1016/j.bmc.2008.11.070 Prostaglandin F2-alpha receptor 3
15357985 10.1016/j.bmcl.2004.06.037 Prostaglandin F2-alpha receptor 3
14631946 10.1152/ajprenal.00402.2002 Solute carrier organic anion transporter family member 3A1 3
10484490 10.1152/ajpregu.1999.277.3.r734 Solute carrier organic anion transporter family member 2A1 3
19101156 10.1016/j.bmc.2008.11.070 Oryctolagus cuniculus 3
20014752 10.1021/tx900326k Hepatotoxicity 3
7277390 10.1021/jm00139a014 Cricetinae gen. sp. 2
10973807 10.1006/bbrc.2000.3377 Solute carrier organic anion transporter family member 2B1 2
11907186 10.1124/jpet.301.1.293 Solute carrier family 22 member 2 2
11907186 10.1124/jpet.301.1.293 Solute carrier family 22 member 1 2
10978187 10.1021/jm990587w Unchecked 2
11907186 10.1124/jpet.301.1.293 Organic anion transporter 3 2
11907186 10.1124/jpet.301.1.293 Solute carrier family 22 member 11 2
2909739 10.1021/jm00121a046 Prostaglandin F2-alpha receptor 2
6876076 10.1021/jm00362a001 Homo sapiens 2
6876076 10.1021/jm00362a001 Monkey 2

Data from ChEMBL 36 via Core Engine