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Compound Detail

CHEMBL18797

SULINDAC SULFIDE
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CSc1ccc(/C=C2/C(C)=C(CC(=O)O)c3cc(F)ccc32)cc1

Basic Information

ChEMBL ID CHEMBL18797
Name SULINDAC SULFIDE
Phase Preclinical
Structure Type MOL
InChI Key LFWHFZJPXXOYNR-MFOYZWKCSA-N

Known Names

Cis-sulindac sulfide Sulindac related compound c Sulindac sulfide Sulindac sulfide, (z)- Sulindac sulphide, (z)- Z-sulindac sulfide
16
Targets
41
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names

Molecular Properties

340.4
MW (Da)
5.35
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.76
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Achiral
USAN Stem -ac

Extended Properties

Molecular Formula C20H17FO2S
MW 340.42
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.74

Activity Summary

IC50 33 meas. best 7.3
Ki 5 meas. best 5.46
EC50 3 meas. best 6.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL2949
IC50 7.3 7.3 50.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
IC50 7.08 7.08 84.0 1
Prostaglandin G/H synthase 2
CHEMBL230
IC50 7.0 6.345 100.0 4
Prostaglandin G/H synthase 1
CHEMBL221
IC50 6.94 6.55 115.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
EC50 6.1 6.1 800.0 2
Mitogen-activated protein kinase 1
CHEMBL4040
IC50 5.96 5.96 1092.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.7 5.7 2000.0 1
Prostaglandin D2 receptor 2
CHEMBL5071
Ki 5.46 5.46 3500.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.39 5.39 4087.0 1
Adenosine receptor A3
CHEMBL256
IC50 5.14 5.14 7231.0 1
Unchecked
CHEMBL612545
IC50 4.92 4.5 11986.4 6
Mu-type opioid receptor
CHEMBL233
Ki 4.86 4.86 13667.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 4.86 4.86 13911.0 1
Cysteinyl leukotriene receptor 1
CHEMBL1798
Ki 4.83 4.83 14684.0 1
Epidermal growth factor receptor
CHEMBL203
IC50 4.62 4.62 23981.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 4.56 4.56 27822.0 1
Cysteinyl leukotriene receptor 1
CHEMBL1798
IC50 4.53 4.53 29368.0 1
Mu-type opioid receptor
CHEMBL233
IC50 4.47 4.47 33668.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.41 4.41 38700.0 1
Gamma-secretase
CHEMBL2094135
IC50 4.28 4.2 53000.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 50.0 nM 7.3 Inhibition of ovine COX1 after 5 mins 20503989
Aldo-keto reductase family 1 member B1 IC50 = 84.0 nM 7.08 DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde) -
Prostaglandin G/H synthase 2 IC50 = 100.0 nM 7.0 Inhibition of human recombinant COX2 after 5 mins 20503989
Prostaglandin G/H synthase 1 IC50 = 115.0 nM 6.94 Inhibition of COX1 22263894
Prostaglandin G/H synthase 2 IC50 = 140.0 nM 6.85 Inhibition of COX2 22263894
Prostaglandin G/H synthase 1 IC50 = 688.0 nM 6.16 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Peroxisome proliferator-activated receptor gamma EC50 = 800.0 nM 6.1 Partial agonist activity at GAL4 DBD-fused PPARgamma LBD (unknown origin) expres... 34118723
Peroxisome proliferator-activated receptor gamma EC50 = 800.0 nM 6.1 Agonist activity at PPARgamma expressed in human HCA7 cells assessed as inductio... 18665581
Mitogen-activated protein kinase 1 IC50 = 1092.0 nM 5.96 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Prostaglandin G/H synthase 2 IC50 = 1537.0 nM 5.81 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 1896.0 nM 5.72 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate preincu... 34118723
Cytochrome P450 1A2 IC50 = 2000.0 nM 5.7 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Prostaglandin D2 receptor 2 Ki = 3500.0 nM 5.46 Binding affinity towards human CRTH2 receptor expressed in CHO cells 16190744
Adenosine receptor A3 Ki = 4087.0 nM 5.39 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Adenosine receptor A3 IC50 = 7231.0 nM 5.14 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Unchecked IC50 = 11986.4 nM 4.92 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Mu-type opioid receptor Ki = 13667.0 nM 4.86 DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine... -
D(1A) dopamine receptor Ki = 13911.0 nM 4.86 DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) -
Cysteinyl leukotriene receptor 1 Ki = 14684.0 nM 4.83 DRUGMATRIX: Cysteinyl leukotriene receptor 1 radioligand binding (ligand: [3H]LT... -
Unchecked IC50 = 19964.0 nM 4.7 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -

Literature References

PubMed DOI Target Context # Activities
17573346 10.1074/jbc.m700618200 Presenilin-1 15
20650635 10.1016/j.bmcl.2010.06.131 Gamma-secretase 9
17573346 10.1074/jbc.m700618200 Unchecked 4
16455248 10.1016/j.bmcl.2006.01.033 Mus musculus 3
19427206 10.1016/j.bmcl.2009.04.078 Prostaglandin G/H synthase 2 3
19427206 10.1016/j.bmcl.2009.04.078 Prostaglandin G/H synthase 1 3
6276543 10.1021/jm00142a015 Liposome 3
20801552 10.1016/j.ejmech.2010.08.019 MIA PaCa-2 3
24387865 10.1016/j.bmc.2013.12.014 PC-3 3
21383205 10.1124/dmd.110.037663 Skin 2
20801552 10.1016/j.ejmech.2010.08.019 HUVEC 2
21383205 10.1124/dmd.110.037663 Brain 2
34118723 10.1016/j.ejmech.2021.113542 Peroxisome proliferator-activated receptor gamma 2
17932033 10.1074/jbc.m707002200 Gamma-secretase 2
11844707 10.1016/s0960-894x(01)00839-3 MDCK 2
18222570 10.1016/j.ejmech.2007.11.031 Peroxisome proliferator-activated receptor gamma 2
21383205 10.1124/dmd.110.037663 Liver 2
18665581 10.1021/jm700969c Peroxisome proliferator-activated receptor gamma 2
21383205 10.1124/dmd.110.037663 Plasma 2
11844707 10.1016/s0960-894x(01)00839-3 SW480 1

Data from ChEMBL 36 via Core Engine