Compound Detail

CHEMBL139

DICLOFENAC

💊 Approved Drug

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💊 Approved Drug

O=C(O)Cc1ccccc1Nc1c(Cl)cccc1Cl

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL139
Name	DICLOFENAC
Phase	Approved
Structure Type	MOL
InChI Key	DCOPUUMXTXDBNB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Arthrotec Diclofenac Diclofenac acid Diclofenac free acid Diclofenaco LAS-41007 Las41007 Voltaren ophthalmic Voltaren xr Zorvolex Zorvolex capsules

Targets

129

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

296.1

MW (Da)

4.36

ALogP

HBA

HBD

49.3

PSA (Å²)

0.88

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1988
Availability	OTC
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

USAN Stem	-ac
USAN Year	1973

Extended Properties

Molecular Formula	C14H11Cl2NO2
MW	296.15
Aromatic Rings	2
Heavy Atoms	19
NP-Likeness	-0.87

Mechanism of Action

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

Indications

Acute Pain Arthralgia Arthritis, Rheumatoid Cataract Dysmenorrhea Eye Diseases Inflammation Keratosis, Actinic Keratosis, Actinic Migraine Disorders Myalgia Osteoarthritis Rheumatic Diseases Sprains and Strains Infertility Osteoarthritis, Hip Osteoarthritis, Knee Renal Colic Spondylitis, Ankylosing Stomach Ulcer

ATC Classification

D11AX18

diclofenac

Level 1: DERMATOLOGICALS

Level 2: OTHER DERMATOLOGICAL PREPARATIONS

M01AB05

diclofenac

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

M01AB55

diclofenac, combinations

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

M02AA15

diclofenac

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

S01BC03

diclofenac

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning

neurotoxicity

Country: United States

Black Box Warning

gastrointestinal toxicity

Country: United States

Black Box Warning

cardiotoxicity

Country: United States

Activity Summary

IC50 106 meas. best 8.52

Ki 13 meas. best 5.49

Kd 7 meas. best 7.37

EC50 3 meas. best 4.25

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin G/H synthase 1 CHEMBL2860	IC50	8.52	8.52	3.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	8.52	7.225	3.0	12
Prostaglandin G/H synthase 2 CHEMBL230	IC50	8.3	6.6921	5.0	28
Interleukin-8 CHEMBL2157	IC50	8.1	8.1	8.0	1
C-X-C chemokine receptor type 1 CHEMBL4029	IC50	7.92	7.92	12.0	1
Prostaglandin G/H synthase 2 CHEMBL4321	IC50	7.66	7.39	22.0	5
Nucleic Acid CHEMBL345	Kd	7.37	6.995	42.7	4
Prostaglandin G/H synthase 2 CHEMBL4102	IC50	7.22	6.02	60.0	5
Unchecked CHEMBL612545	IC50	7.22	5.571	60.0	10
Transthyretin CHEMBL3194	Kd	7.22	6.61	60.0	2
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	7.17	6.206	67.0	20
Cyclooxygenase CHEMBL2095157	IC50	6.3	6.3	500.0	1
Erythrocyte CHEMBL4296518	IC50	6.03	6.03	942.0	1
Staphylococcus aureus CHEMBL352	IC50	6.03	6.03	943.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	5.72	5.72	1900.0	1
Albumin CHEMBL3253	Kd	5.61	5.61	2454.7	1
Fatty acid-binding protein, liver CHEMBL5738	Ki	5.49	4.97	3220.0	2
Transthyretin CHEMBL3194	IC50	5.43	5.43	3742.0	1
Solute carrier family 22 member 6 CHEMBL1641347	IC50	5.4	5.4	4000.0	1
THP-1 CHEMBL614245	IC50	5.31	5.31	4860.0	1
Calcium/calmodulin-dependent protein kinase type II subunit alpha CHEMBL2359	Ki	5.29	5.29	5100.0	1
Unchecked CHEMBL612545	Ki	5.1	4.71	7900.0	2
Cytochrome c oxidase subunit 2 CHEMBL6174	IC50	5.0	5.0	10050.0	1
RAW264.7 CHEMBL612557	IC50	4.99	4.6363	10180.0	8
UDP-glucuronosyltransferase 1A9 CHEMBL1743319	Ki	4.96	4.96	11000.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	4.89	4.89	12890.0	1
UDP-glucuronosyltransferase 1A7 CHEMBL1743317	Ki	4.72	4.72	19000.0	1
UDP-glucuronosyltransferase 1-6 CHEMBL1743316	Ki	4.64	4.64	23000.0	1
UDP-glucuronosyltransferase 1A10 CHEMBL1743320	Ki	4.55	4.55	28000.0	1
Bile salt export pump CHEMBL6020	IC50	4.36	4.275	44000.0	2
UDP-glucuronosyltransferase 1A1 CHEMBL1287617	Ki	4.28	4.28	52000.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	4.25	4.225	56000.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	65000.0	ng.hr.mL-1	Rattus norvegicus
AUC	490.22	ng.hr.mL-1	Homo sapiens
AUC	478.36	ng.hr.mL-1	Homo sapiens
AUC	499.21	ng.hr.mL-1	Homo sapiens
AUC	487.47	ng.hr.mL-1	Homo sapiens
AUC	1004.66	ng.hr.mL-1	Homo sapiens
AUC	979.75	ng.hr.mL-1	Homo sapiens
AUC	1001.13	ng.hr.mL-1	Homo sapiens
AUC	978.94	ng.hr.mL-1	Homo sapiens
AUC	861.2	ng.hr.mL-1	Homo sapiens
AUC	837.29	ng.hr.mL-1	Homo sapiens
AUC	876.14	ng.hr.mL-1	Homo sapiens
AUC	851.96	ng.hr.mL-1	Homo sapiens
AUC	1318.84	ng.hr.mL-1	Homo sapiens
AUC	1287.31	ng.hr.mL-1	Homo sapiens
AUC	1334.06	ng.hr.mL-1	Homo sapiens
AUC	1301.96	ng.hr.mL-1	Homo sapiens
AUC	1178.01	ng.hr.mL-1	Homo sapiens
AUC	1150.4	ng.hr.mL-1	Homo sapiens
AUC	1204.03	ng.hr.mL-1	Homo sapiens
AUC	1175.87	ng.hr.mL-1	Homo sapiens
AUC	691.0	ng.hr.mL-1	Homo sapiens
AUC	680.0	ng.hr.mL-1	Homo sapiens
AUC	1521.0	ng.hr.mL-1	Homo sapiens
AUC	1416.0	ng.hr.mL-1	Homo sapiens
AUC	706.0	ng.hr.mL-1	Homo sapiens
AUC	713.0	ng.hr.mL-1	Homo sapiens
AUC	1549.0	ng.hr.mL-1	Homo sapiens
AUC	1457.0	ng.hr.mL-1	Homo sapiens
AUC	1197.0	ng.hr.mL-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin G/H synthase 1	IC50	=	3.0	nM	8.52	Inhibition of COX1 in bovine platelets assessed as formation of 12-hydroxyheptad...	19097798
Prostaglandin G/H synthase 1	IC50	=	3.0	nM	8.52	Inhibition of COX1	22236250
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Inhibitory concentration against COX-2 upon incubation for 15 minutes at 37 degr...	16250658
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Inhibition of COX2	22236250
Interleukin-8	IC50	=	8.0	nM	8.1	Inhibition of CXCL8-induced chemotaxis in human polymorphonuclear leukocyte pret...	19560921
Prostaglandin G/H synthase 2	IC50	=	10.0	nM	8.0	Inhibition of COX2 in LPS-stimulated human blood	19097798
Prostaglandin G/H synthase 1	IC50	=	12.0	nM	7.92	Inhibition of human COX1-mediated conversion of arachidonic acid to prostaglandi...	18095641
Prostaglandin G/H synthase 1	IC50	=	12.0	nM	7.92	Inhibition of cyclooxygenase 1	18811132
Prostaglandin G/H synthase 1	IC50	=	12.0	nM	7.92	Inhibition of COX1 assessed as inhibition of arachidonic acid conversion to pros...	19191553
C-X-C chemokine receptor type 1	IC50	=	12.0	nM	7.92	Inhibition of wild type CXCR1 transfected in mouse L1.2 cells assessed as inhibi...	19560921
Prostaglandin G/H synthase 1	IC50	=	13.0	nM	7.89	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Prostaglandin G/H synthase 1	IC50	=	15.0	nM	7.82	Inhibition of human cyclooxygenase 1	18588282
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Enzyme (COXs) Inhibition Assay: The inhibitory effects of candidate compounds on...	-
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Inhibition of human COX-2 using arachidonic acid as substrate preincubated for 1...	34137625
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Inhibition of human COX2 using arachidonic acid as substrate incubated for 10 mi...	31843462
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Inhibition of human recombinant COX2 assessed as reduction in PGH2-derived PGF2a...	27019010
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Inhibition of COX2	17341061
Prostaglandin G/H synthase 2	IC50	=	20.0	nM	7.7	Inhibition of human recombinant COX2 using arachidonic acid as substrate incubat...	24332492
Prostaglandin G/H synthase 2	IC50	=	22.0	nM	7.66	Inhibition of mouse COX2 for 20 mins pre-incubated before addition of [1-14C]ara...	17434872
Prostaglandin G/H synthase 2	IC50	=	22.0	nM	7.66	Inhibition of mouse COX2 for 17 mins pre-incubated before addition of [1-14C]ara...	17434872

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1414
-	10.6019/CHEMBL3885881	Rattus norvegicus	825
-	10.6019/CHEMBL5058577	U2OS	304
-	10.6019/CHEMBL5724801	U2OS	304
-	10.6019/CHEMBL5058577	HEK-293T	304
-	10.6019/CHEMBL5058577	Fibroblast	304
-	10.6019/CHEMBL5724801	Fibroblast	304
-	10.6019/CHEMBL5724801	HEK-293T	304
22275465	10.1124/dmd.111.043984	ADMET	19
30234983	10.1021/acs.jmedchem.8b00999	Unchecked	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
29604541	10.1016/j.ejmech.2018.03.048	Unchecked	12
29197735	10.1016/j.ejmech.2017.11.075	Unchecked	12
36520541	10.1021/acs.jmedchem.2c01368	ADMET	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
32985885	10.1021/acs.jmedchem.0c01033	ADMET	11
29544150	10.1016/j.ejmech.2018.02.075	Unchecked	10
36680883	10.1016/j.ejmech.2022.115076	ADMET	10
20594837	10.1016/j.bmcl.2010.06.058	Rattus norvegicus	9

Data from ChEMBL 36 via Core Engine