Compound Detail

CHEMBL521

IBUPROFEN

💊 Approved Drug

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💊 Approved Drug

CC(C)Cc1ccc(C(C)C(=O)O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL521
Name	IBUPROFEN
Phase	Approved
Structure Type	MOL
InChI Key	HEFNNWSXXWATRW-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Aches-n-pain Advil Advil liqui-gels Advil migraine liqui-gels Anadin joint pain Anadin liquifast Anadin period pain relief Anadin ultra Apsifen Apsifen-f Arthrofen 200 Arthrofen 400 +18 more

Targets

170

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

206.3

MW (Da)

3.07

ALogP

HBA

HBD

37.3

PSA (Å²)

0.82

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1974
Availability	OTC
Chirality	Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-profen
USAN Year	1968

Extended Properties

Molecular Formula	C13H18O2
MW	206.28
Aromatic Rings	1
Heavy Atoms	15
NP-Likeness	0.14

Mechanism of Action

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

Indications

Acute Pain Arthralgia Arthritis Arthritis, Juvenile Arthritis, Rheumatoid Back Pain Cardiovascular Diseases Common Cold Ductus Arteriosus, Patent Dysmenorrhea Fever Headache Influenza, Human Migraine Disorders Muscle Cramp Myalgia Osteoarthritis Pain Pharyngitis Rheumatic Diseases

ATC Classification

C01EB16

ibuprofen

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CARDIAC THERAPY

G02CC01

ibuprofen

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: OTHER GYNECOLOGICALS

M01AE01

ibuprofen

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

M01AE51

ibuprofen, combinations

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

M02AA13

ibuprofen

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

R02AX02

ibuprofen

Level 1: RESPIRATORY SYSTEM

Level 2: THROAT PREPARATIONS

Drug Warnings

Black Box Warning

gastrointestinal toxicity

Country: United States

Black Box Warning

neurotoxicity

Country: United States

Black Box Warning

cardiotoxicity

Country: United States

Black Box Warning

vascular toxicity

Country: United States

Activity Summary

IC50 151 meas. best 7.0

Ki 15 meas. best 5.96

Kd 3 meas. best 5.83

EC50 1 meas. best 4.57

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin G/H synthase 2 CHEMBL230	IC50	7.0	5.3971	100.0	34
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.67	5.3643	212.0	14
Prostaglandin G/H synthase (cyclooxygenase) CHEMBL2111349	IC50	6.66	6.66	220.0	1
RAW264.7 CHEMBL612557	IC50	6.41	5.2975	390.0	4
Cyclooxygenase CHEMBL2095157	IC50	6.22	5.96	600.0	2
Prostaglandin G/H synthase 2 CHEMBL4321	IC50	6.07	6.07	860.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	5.97	5.3179	1060.0	33
Solute carrier family 22 member 20 CHEMBL5269	Ki	5.96	5.955	1100.0	2
Prostaglandin G/H synthase 2 CHEMBL3331	IC50	5.96	5.96	1100.0	1
Prostaglandin G/H synthase 2 CHEMBL4102	IC50	5.96	5.9463	1100.0	8
Albumin CHEMBL4817	Kd	5.83	5.83	1470.0	1
Prostaglandin G/H synthase 1 CHEMBL2860	IC50	5.54	5.18	2900.0	4
Albumin CHEMBL3728	IC50	5.52	5.52	3000.0	1
Solute carrier family 22 member 6 CHEMBL1777665	Ki	5.46	5.46	3500.0	1
Solute carrier family 22 member 6 CHEMBL5653	Ki	5.33	5.33	4677.4	2
Solute carrier family 22 member 6 CHEMBL1641347	IC50	5.1	5.1	8000.0	1
Prostaglandin G/H synthase 2 CHEMBL4102	Ki	5.05	5.05	9000.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	Ki	5.05	5.05	9000.0	1
Aldo-keto reductase family 1 member C3 CHEMBL4681	IC50	5.0	4.74	10000.0	2
Homo sapiens CHEMBL372	IC50	4.95	4.95	11200.0	1
Unchecked CHEMBL612545	IC50	4.95	4.95	11200.0	1
Neutrophil CHEMBL613710	IC50	4.92	4.6567	12100.0	3
Prostaglandin-H2 D-isomerase CHEMBL4334	IC50	4.89	4.89	13000.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	4.85	4.85	14000.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	4.77	4.77	17000.0	1
RAW264.7 CHEMBL612557	EC50	4.57	4.57	26740.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.56	4.4167	27530.0	3
Fatty acid-binding protein, liver CHEMBL5738	Ki	4.32	4.32	47600.0	1
Cytochrome P450 2C9 CHEMBL3397	Ki	4.3	4.3	50000.0	1
ADMET CHEMBL612558	Kd	4.28	4.28	52700.0	1
Albumin CHEMBL3253	Kd	4.14	4.14	73000.0	1
SK-LU-1 CHEMBL614913	IC50	4.04	4.04	90610.0	1
MCF7 CHEMBL387	IC50	4.04	4.04	92140.0	1
Dehydrogenase/reductase SDR family member 9 CHEMBL1075220	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	56766.65	ng.hr.mL-1	Mus musculus
AUC	14000.0	ng.hr.mL-1	Rattus norvegicus
AUC	1856215.0	ug/g.min	Mus musculus
AUC	54251.64	ng.hr.mL-1	Rattus norvegicus
AUC	13841.39	ng.hr.mL-1	Rattus norvegicus
CL	1.4	mL.min-1.kg-1	Homo sapiens
CL	0.82	mL.min-1.kg-1	Homo sapiens
CL	0.8	mL.min-1.kg-1	Homo sapiens
CL	0.82	mL.min-1.kg-1	Homo sapiens
CL	0.82	mL.min-1.kg-1	Homo sapiens
CL	56.2	mL.min-1.kg-1	Homo sapiens
CL	3.29	uL.min-1.(10^6cells)-1	Homo sapiens
CL	0.81	mL.min-1.kg-1	Homo sapiens
CL	3.8	mL.min-1.kg-1	Mus musculus
CL	13.3	uL.min-1.(10^6cells)-1	Homo sapiens
CL	0.82	mL.min-1.kg-1	Homo sapiens
CL	61.0	mL.min-1.kg-1	Homo sapiens
CL	6.5	mL.min-1.kg-1	Rattus norvegicus
CL	3.1	mL.min-1.kg-1	Macaca fascicularis
CL	0.8	mL.min-1.kg-1	Homo sapiens
Cmax	137.82	nM	Mus musculus
Cmax	10.68	ug/g	Mus musculus
Cmax	27632.34	nM	Rattus norvegicus
Cmax	10681.0	ug/g	Mus musculus
Cmax	80200.0	nM	Rattus norvegicus
Cmax	41800.0	nM	Rattus norvegicus
F	80.0	%	Homo sapiens
F	85.0	%	Homo sapiens
F	100.0	%	Rattus norvegicus
F	78.42	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin G/H synthase 2	IC50	=	100.0	nM	7.0	Inhibition activity against recombinant human Prostaglandin G/H synthase 2	9057869
Prostaglandin G/H synthase 1	IC50	=	212.0	nM	6.67	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Prostaglandin G/H synthase (cyclooxygenase)	IC50	=	220.0	nM	6.66	Inhibition of PGE-2 production in 3T3 (murine fibroblast) cell culture.	8568814
Prostaglandin G/H synthase 1	IC50	=	290.0	nM	6.54	Inhibition of COX-1 in human washed platelet assessed as inhibition of 0.5 uM ar...	23651359
RAW264.7	IC50	=	390.0	nM	6.41	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-...	28408221
Cyclooxygenase	IC50	=	600.0	nM	6.22	Inhibition of COX in RBL1 cells assessed as reduction in PGE2/D2 production usin...	28835803
Prostaglandin G/H synthase 2	IC50	=	860.0	nM	6.07	Inhibition of COX-2 in mouse RAW264.7 cells assessed as decrease in LPS-induced ...	24656662
Prostaglandin G/H synthase 1	IC50	=	1060.0	nM	5.97	Reversible competitive inhibition of prostaglandin G/H synthase 1	14741265
Prostaglandin G/H synthase 2	IC50	=	1080.0	nM	5.97	Inhibition of recombinant human N-terminal His-tagged COX2 expressed in baculovi...	29373271
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2 by enzyme immunoassay	19500994
Solute carrier family 22 member 20	Ki	=	1100.0	nM	5.96	Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr	17553798
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2 by enzyme immuno assay	26691756
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of recombinant human COX-2 preincubated for 15 mins by fluorescence a...	26487917
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2	23200247
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2	22148253
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of ovine COX2 by enzyme immuno assay	21890358
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2 by enzyme immuno assay	21641217
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human COX2 by enzyme immunoassay	20576432
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant COX2 by enzyme immuno assay	20202839
Prostaglandin G/H synthase 2	IC50	=	1100.0	nM	5.96	Inhibition of ovine COX2 by enzyme immuno assay	17509888

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1385
-	10.6019/CHEMBL3885881	Rattus norvegicus	716
30711830	10.1016/j.ejmech.2019.01.046	Staphylococcus aureus	37
28949138	10.1021/acs.jmedchem.7b01072	Acid-sensing ion channel 1	34
-	10.1039/C5MD00551E	No relevant target	28
26833243	10.1016/j.bmc.2016.01.026	Candida albicans	24
30711830	10.1016/j.ejmech.2019.01.046	Cell membrane	23
16472241	10.2174/1570163043334794	Hepatotoxicity	18
26833243	10.1016/j.bmc.2016.01.026	Meyerozyma guilliermondii	18
6502598	10.1021/jm00378a027	Rattus norvegicus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
36796127	10.1016/j.bmc.2023.117203	No relevant target	13
32311607	10.1016/j.ejmech.2020.112293	Mus musculus	12
20171760	10.1016/j.ejmech.2010.01.020	Rattus norvegicus	12
31191865	10.1039/C8MD00611C	ADMET	12
26833243	10.1016/j.bmc.2016.01.026	Nakaseomyces glabratus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
-	10.1007/s00044-012-0329-y	Rattus norvegicus	11
32311607	10.1016/j.ejmech.2020.112293	Rattus norvegicus	11
32985885	10.1021/acs.jmedchem.0c01033	ADMET	11

Data from ChEMBL 36 via Core Engine