Compound Detail

CHEMBL15770

SULINDAC

💊 Approved Drug

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💊 Approved Drug

CC1=C(CC(=O)O)c2cc(F)ccc2/C1=C\c1ccc([S+](C)[O-])cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL15770
Name	SULINDAC
Phase	Approved
Structure Type	MOL
InChI Key	MLKXDPUZXIRXEP-MFOYZWKCSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL18797

Known Names

Arthrocine Artribid Clinoril MK-231 NSC-757344 Sulindac Sulindaco

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

356.4

MW (Da)

4.37

ALogP

HBA

HBD

60.4

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1978
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Prodrug

USAN Stem	-ac
USAN Year	1975

Extended Properties

Molecular Formula	C20H17FO3S
MW	356.42
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.29

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cyclooxygenase inhibitor	INHIBITOR	Cyclooxygenase	✓	✓

Indications

Arthritis, Rheumatoid Osteoarthritis Rheumatic Diseases Spondylitis Adenomatous Polyposis Coli Colorectal Neoplasms Colorectal Neoplasms Precancerous Conditions Breast Neoplasms Carcinoma, Squamous Cell Desmoid Tumors Fragile X Syndrome Leukemia, Myeloid, Acute Melanoma

ATC Classification

M01AB02

sulindac

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Black Box Warning

gastrointestinal toxicity

Country: United States

Black Box Warning

cardiotoxicity

Country: United States

Black Box Warning

neurotoxicity

Country: United States

Activity Summary

IC50 22 meas. best 6.53

Ki 3 meas. best 4.11

EC50 2 meas. best 6.42

Kd 2 meas. best 6.24

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	6.53	6.53	293.0	2
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	6.43	6.43	374.0	1
Glycine receptor subunit alpha-1 CHEMBL5845	EC50	6.42	6.42	380.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	6.36	6.36	435.0	1
Complement C5 CHEMBL2364163	Kd	6.24	6.24	570.0	1
Unchecked CHEMBL612545	Kd	5.47	5.47	3420.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	5.06	5.06	8800.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	4.8	4.8	16000.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	4.64	4.64	22650.0	1
Bile salt export pump CHEMBL6020	IC50	4.2	4.2	63690.0	1
Lactoylglutathione lyase CHEMBL2424	Ki	4.11	4.11	77900.0	1
Prostaglandin E synthase CHEMBL5658	IC50	4.1	4.1	80000.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	IC50	4.08	4.08	82900.0	1
Bile salt export pump CHEMBL2073674	IC50	4.06	4.06	87500.0	1
REF CHEMBL614853	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	3.0	mL.min-1.g-1	Homo sapiens
CL	5.6	mL.min-1.kg-1	Mus musculus
CL	2.0	uL.min-1.(10^6cells)-1	Homo sapiens
Fu	0.069	-	Homo sapiens
T1/2	1.2	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	293.0	nM	6.53	Inhibition of calf ALR2	23246355
Unchecked	IC50	=	293.0	nM	6.53	Inhibition of Calf ALR2 in presence of NADPH by UV spectrophotometric analysis	29751237
Aldo-keto reductase family 1 member B1	IC50	=	374.0	nM	6.43	Inhibition of Homo sapiens (human) aldose reductase	-
Glycine receptor subunit alpha-1	EC50	=	380.0	nM	6.42	Potentiation of human GlyR-alpha1 expressed in Xenopus laevis oocytes assessed a...	25790278
Aldo-keto reductase family 1 member B1	IC50	=	435.0	nM	6.36	DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde)	-
Complement C5	Kd	=	570.0	nM	6.24	Binding affinity to human C5a assessed as dissociation constant after 1 hr by ci...	31447248
Unchecked	Kd	=	3420.0	nM	5.47	Binding affinity to wild type TTR/Amyloid beta (1 to 40 residues) binary complex...	34555615
Prostaglandin G/H synthase 2	IC50	=	8800.0	nM	5.06	Inhibition of recombinant human COX-2 preincubated for 15 mins by fluorescence a...	26487917
Prostaglandin G/H synthase 1	IC50	=	16000.0	nM	4.8	Inhibition of Ovine COX-1 preincubated for 15 mins by fluorescence analysis	26487917
Peroxisome proliferator-activated receptor gamma	EC50	=	22650.0	nM	4.64	Partial agonist activity at GAL4 DBD-fused PPARgamma LBD (unknown origin) expres...	34118723
Bile salt export pump	IC50	=	63690.0	nM	4.2	Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21...	22961681
Lactoylglutathione lyase	Ki	=	77900.0	nM	4.11	Inhibition of glyoxalase 1	21237663
Prostaglandin E synthase	IC50	=	80000.0	nM	4.1	Inhibition of microsomal PGES	21920764
Retinoic acid receptor RXR-alpha	IC50	=	82900.0	nM	4.08	Displacement of [3H]-9-cis-RA from RXRalpha (unknown origin) by liquid scintilla...	23434637
Bile salt export pump	IC50	=	87500.0	nM	4.06	Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S...	21965623
REF	IC50	=	100000.0	nM	4.0	Anti-proliferative activity was evaluated by its ability to inhibit proliferatio...	11844707

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	1397
-	10.6019/CHEMBL3885861	Rattus norvegicus	1391
-	10.5281/zenodo.13943903	ADMET	85
16472241	10.2174/1570163043334794	Hepatotoxicity	18
21051535	10.1124/dmd.110.034629	ADMET	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
31447248	10.1016/j.bmc.2019.115052	Complement C5	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
309947	10.1021/jm00209a001	Rattus norvegicus	5
23434637	10.1016/j.ejmech.2013.01.012	Retinoic acid receptor RXR-alpha	4
35439009	10.1021/acs.jmedchem.1c02207	MIA PaCa-2	4
21405086	10.1021/jm101450p	N2a	4
31995375	10.1021/acs.jmedchem.0c00046	Albumin	4
34555615	10.1016/j.ejmech.2021.113847	Unchecked	4
24387865	10.1016/j.bmc.2013.12.014	PC-3	3
25790278	10.1021/jm501873p	Glycine receptor subunit alpha-1	3
32987314	10.1016/j.ejmech.2020.112864	SW480	3
19144452	10.1016/j.ejmech.2008.11.012	Mus musculus	3

Data from ChEMBL 36 via Core Engine