IBUPROFEN

Search structure
Trade Names:
Synonyms:
Status: Approved (1974)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C01EB16
UNII: WK2XYI10QM

Structure
InChI Key HEFNNWSXXWATRW-UHFFFAOYSA-N
Smile CC(C)Cc1ccc(C(C)C(=O)O)cc1
InChI
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H18O2
Molecular Weight 206.28
AlogP 3.07
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 15.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.97 - EXP
pKa Dissociation Constant 4.91 - EXP
Henry's Law Constant 1.50E-07 atm-m3/mole EST
Atmospheric OH Rate Constant 1.16E-11 cm3/molecule-sec EST
Melting Point 76 deg C EXP
Water Solubility 21 mg/L EXP
Vapor Pressure 1.86E-04 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase inhibitor ISBN Wikipedia
Primary Target
COX-1
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 47600 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 50000 -
Enzyme Hydrolase
- - - - 71-100
Enzyme Isomerase
- 13000 - - -
Enzyme Oxidoreductase
- 1060-72800 - 9000 6-100
Enzyme Protease Aspartic protease Aspartic protease AD clan Aspartic protease A22A subfamily Aspartic protease A22A regulatory subfamily
- - - - 41
Enzyme
- 1060-72800 - 50000 6-100
Ion channel Ligand-gated ion channel Acid-sensing ion channel
- - - - 92
Ion channel Other ion channel Miscellaneous ion channel Presenilin ER Ca2+ leak channel family
- - - - 41
Secreted protein
- 3000 1470 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 47-112
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - 1100-1122 6

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Ductus Arteriosus, Patent 4 D004374 ClinicalTrials
Headache 4 D006261 ClinicalTrials
Peptic Ulcer 3 D010437 ClinicalTrials
Vasculitis 3 D014657 ClinicalTrials
Burns 3 D002056 ClinicalTrials
Sprains and Strains 3 D013180 ClinicalTrials
Sleep Apnea, Obstructive 3 D020181 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Neck Pain 3 D019547 ClinicalTrials
Pulpitis 3 D011671 ClinicalTrials
Shock, Septic 3 D012772 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Causalgia 3 D002422 ClinicalTrials
Cerebral Palsy 3 D002547 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Hypospadias 3 D007021 ClinicalTrials
Fractures, Bone 3 D050723 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Altitude Sickness 3 D000532 ClinicalTrials
Enuresis 2 D004775 ClinicalTrials
Bronchopulmonary Dysplasia 2 D001997 ClinicalTrials
Emphysema 2 D004646 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Spondylarthropathies 2 D025242 ClinicalTrials
Hemorrhage 2 D006470 ClinicalTrials
Retinopathy of Prematurity 2 D012178 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Periodontitis 2 D010518 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Muscular Diseases 2 D009135 ClinicalTrials
Stomatitis, Aphthous 2 D013281 ClinicalTrials
Sunburn 2 D013471 ClinicalTrials
Sinusitis 2 D012852 ClinicalTrials
Brachial Plexus Neuritis 2 D020968 ClinicalTrials
Tooth Diseases 2 D014076 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Granulomatous Disease, Chronic 2 D006105 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Pre-Eclampsia 2 D011225 ClinicalTrials
Epilepsies, Partial 2 D004828 ClinicalTrials
Spondylosis 2 D055009 ClinicalTrials
Pancreatitis 2 D010195 ClinicalTrials
Tension-Type Headache 2 D018781 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Rhinitis, Allergic, Seasonal 1 D006255 ClinicalTrials
Osteoarthritis, Knee 1 D020370 ClinicalTrials
Hypotension, Orthostatic 1 D007024 ClinicalTrials
Premature Birth 1 D047928 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Muscular Dystrophy, Duchenne 1 D020388 ClinicalTrials
Malaria 1 D008288 ClinicalTrials
Temporomandibular Joint Disorders 1 D013705 ClinicalTrials
Ankle Fractures 0 D064386 ClinicalTrials

Related Entries

MCS

UNKNOWN
Salt
Salt
Mixture
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Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 57.5
Gastrointestinal disorders Nausea 53.0
Nervous system disorders Intraventricular haemorrhage 29.0
Respiratory, thoracic and mediastinal disorders Apnoea 28.0
Nervous system disorders Headache 27.0
Respiratory, thoracic and mediastinal disorders Apnoea
Blood and lymphatic system disorders Eosinophilia
Nervous system disorders Intraventricular haemorrhage
Blood and lymphatic system disorders Eosinophilia 23.3
Gastrointestinal disorders Vomiting 22.4
Gastrointestinal disorders Constipation 22.0
Gastrointestinal disorders Gastrointestinal disorder 22.0
Nervous system disorders Somnolence 22.0
Gastrointestinal disorders Nausea 21.0
Infections and infestations Respiratory tract infection 19.0
Gastrointestinal disorders Gastrointestinal disorder
Metabolism and nutrition disorders Hypokalaemia
Gastrointestinal disorders Vomiting
Blood and lymphatic system disorders Anaemia 16.7
Gastrointestinal disorders Flatulence 16.1
Skin and subcutaneous tissue disorders Skin lesion 16.0
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Vomiting 15.1
Nervous system disorders Intraventricular haemorrhage 15.0
Blood and lymphatic system disorders Anaemia
Cardiac disorders Dizziness 14.0
Infections and infestations Bacteraemia 13.3
Metabolism and nutrition disorders Hypokalaemia 13.3
Investigations Haemoglobin
Vascular disorders Haemorrhage
Nervous system disorders Intraventricular haemorrhage
Infections and infestations Respiratory tract infection
Gastrointestinal disorders Dyspepsia 12.0
Metabolism and nutrition disorders Hypocalcaemia 12.0
Endocrine disorders Hypoglycaemia 12.0
Nervous system disorders Headache 11.5
Nervous system disorders Headache
Investigations Blood lactate dehydrogenase increased 10.0
Gastrointestinal disorders Diarrhoea 10.0
Hepatobiliary disorders Hypoalbuminaemia 10.0
Hepatobiliary disorders Hypoproteinaemia 10.0
Nervous system disorders Intraventricular haemorrhage
Infections and infestations Pneumonia bacterial 10.0
Metabolism and nutrition disorders Respiratory failure 10.0
Blood and lymphatic system disorders Thrombocytosis 10.0
Investigations Haemoglobin 9.7
Vascular disorders Haemorrhage 9.7
Metabolism and nutrition disorders Hypocalcaemia
Infections and infestations Urinary tract infection 9.0
Nervous system disorders Headache 8.96
Gastrointestinal disorders Flatulence 7.46
Gastrointestinal disorders Diarrhoea
Hepatobiliary disorders Hypoproteinaemia
Blood and lymphatic system disorders Neutropenia
Endocrine disorders Adrenal insufficiency 7.0
Investigations Blood urea increased 7.0
Metabolism and nutrition disorders Hypernatraemia 7.0
Metabolism and nutrition disorders Hypernatraemia 6.67
Blood and lymphatic system disorders Neutropenia 6.67
Investigations Haemoglobin 6.0
Vascular disorders Haemorrhage 6.0
Endocrine disorders Hypoglycaemia
Renal and urinary disorders Renal failure 6.0
Renal and urinary disorders Renal impairment 6.0
Skin and subcutaneous tissue disorders Skin lesion
Cardiac disorders Dizziness 5.97
Investigations Haemoglobin
Vascular disorders Haemorrhage
Renal and urinary disorders Urinary retention 5.22
Gastrointestinal disorders Dyspepsia 4.48
Cardiac disorders Dizziness 4.28
Investigations Haemoglobin 4.28
Vascular disorders Haemorrhage 4.28
Respiratory, thoracic and mediastinal disorders Atelectasis 4.0
Investigations Blood urea increased
Metabolism and nutrition disorders Hypernatraemia
General disorders and administration site conditions Oedema 4.0
Respiratory, thoracic and mediastinal disorders Pneumothorax 4.0
Renal and urinary disorders Renal failure
Renal and urinary disorders Renal impairment
Metabolism and nutrition disorders Respiratory failure
Infections and infestations Urinary tract infection
Blood and lymphatic system disorders Anaemia 3.73
Metabolism and nutrition disorders Hypokalaemia 3.73
Investigations Blood lactate dehydrogenase increased
Hepatobiliary disorders Hypoalbuminaemia
Vascular disorders Hypotension
Renal and urinary disorders Urinary retention
Renal and urinary disorders Urinary retention 3.29
Investigations Blood creatinine increased 3.0
Renal and urinary disorders Renal failure
Investigations Urine output 3.0
Gastrointestinal disorders Abdominal discomfort 2.99
Respiratory, thoracic and mediastinal disorders Cough 2.99
Investigations Haemoglobin decreased 2.99
Injury, poisoning and procedural complications Wound haemorrhage 2.99
Cardiac disorders Oedema peripheral 2.96
Metabolism and nutrition disorders Hypokalaemia
Blood and lymphatic system disorders Anaemia 2.3
Blood and lymphatic system disorders Anaemia
Investigations Haemoglobin decreased 1.97
Cardiac disorders Dizziness
Cardiac disorders Oedema peripheral
Injury, poisoning and procedural complications Wound haemorrhage
Gastrointestinal disorders Dyspepsia 1.32
Injury, poisoning and procedural complications Wound haemorrhage 1.32
Investigations Haemoglobin decreased
Endocrine disorders Adrenal insufficiency
Respiratory, thoracic and mediastinal disorders Atelectasis
Investigations Blood creatinine increased
Investigations Blood urea increased
Investigations Blood urea increased 1.0
Renal and urinary disorders Haematuria
Renal and urinary disorders Haematuria 1.0
Respiratory, thoracic and mediastinal disorders Pneumothorax
Skin and subcutaneous tissue disorders Pruritus 1.0
Renal and urinary disorders Renal failure 1.0
Investigations Urine output
Metabolism and nutrition disorders Hypokalaemia 0.987
Cardiac disorders Oedema peripheral 0.746
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Abdominal discomfort 0.658
Respiratory, thoracic and mediastinal disorders Cough 0.658
Respiratory, thoracic and mediastinal disorders Cough

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
13.17
Injury, poisoning and procedural complications
11.34
General disorders and administration site conditions
11.15
Vascular disorders
7.79
Skin and subcutaneous tissue disorders
7.5
Immune system disorders
7.27
Nervous system disorders
6.66
Respiratory, thoracic and mediastinal disorders
5.43
Psychiatric disorders
4.46
Cardiac disorders
3.84
Investigations
2.93
Renal and urinary disorders
2.87
Infections and infestations
2.52
Musculoskeletal and connective tissue disorders
2.24
Metabolism and nutrition disorders
2.1

Cross References

Resources Reference
CAS NUMBER 15687-27-1
ChEBI 5855
ChEMBL CHEMBL521
DrugBank DB01050
DrugCentral 1407
EPA CompTox DTXSID5020732
FDA SRS WK2XYI10QM
Human Metabolome Database HMDB0001925
Guide to Pharmacology 2713
KEGG C01588
PDB IBP
PharmGKB PA449957
PubChem 3672
SureChEMBL SCHEMBL3001
ZINC ZINC38141759
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