CELECOXIB

Search structure
Trade Names:
Synonyms:
Status: Approved (1998) Withdrawn (2011)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01XX33
UNII: JCX84Q7J1L

Structure
InChI Key RZEKVGVHFLEQIL-UHFFFAOYSA-N
Smile Cc1ccc(-c2cc(C(F)(F)F)nn2-c2ccc(S(N)(=O)=O)cc2)cc1
InChI
InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H14F3N3O2S
Molecular Weight 381.38
AlogP 3.51
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 77.98
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase-2 inhibitor DailyMed
Primary Target
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 10000 - - -
Enzyme Isomerase
- 425-540 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PDK1 subfamily
- 48000-48000 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase p38 subfamily
- 810 - - -
Enzyme Lyase
- 21-21 - 21-21000 -
Enzyme Oxidoreductase
- 1-3600 - - 0-100
Enzyme
- 1-3600 - 21-21000 0-100
Epigenetic regulator Eraser Histone deacetylase HDAC class I
- 1185 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
- 1637 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- 1637 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
- 1637 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 10600 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - - 95
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22-143
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 8
Transporter Electrochemical transporter
- - - - 22-143
Transporter Primary active transporter Oxidoreduction-driven transporters
- 280-540 - - 100

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hemorrhage 4 D006470 ClinicalTrials
Osteoarthritis 4 D010003 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Migraine Disorders 4 D008881 ClinicalTrials
Peptic Ulcer 4 D010437 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Pharyngitis 3 D010612 ClinicalTrials
Liver Neoplasms 3 D008113 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Head and Neck Neoplasms 3 D006258 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Gout 3 D006073 ClinicalTrials
Memory Disorders 3 D008569 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Pancreatic Neoplasms 3 D010190 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Nasopharyngeal Neoplasms 3 D009303 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Depression, Postpartum 3 D019052 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Adenoma 3 D000236 ClinicalTrials
Tobacco Use Disorder 3 D014029 ClinicalTrials
Hand-Foot Syndrome 3 D060831 ClinicalTrials
Macular Degeneration 3 D008268 ClinicalTrials
Osteoarthritis, Hip 3 D015207 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Influenza, Human 3 D007251 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Bipolar Disorder 3 D001714 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Pre-Eclampsia 2 D011225 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Lymphangioleiomyomatosis 2 D018192 ClinicalTrials
Prostatic Hyperplasia 2 D011470 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Paraproteinemias 2 D010265 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Papillomavirus Infections 2 D030361 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Temporomandibular Joint Disorders 2 D013705 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Graves Ophthalmopathy 2 D049970 ClinicalTrials
Stomatitis 2 D013280 ClinicalTrials
Neurofibromatosis 1 2 D009456 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Muscular Atrophy, Spinal 2 D009134 ClinicalTrials
Facial Pain 2 D005157 ClinicalTrials
Rotator Cuff Injuries 2 D000070636 ClinicalTrials
Tonsillitis 2 D014069 ClinicalTrials
Toothache 2 D014098 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Papilloma 2 D010212 ClinicalTrials
Uterine Neoplasms 2 D014594 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Squamous Intraepithelial Lesions 2 D000081483 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 2 D000077195 ClinicalTrials
Obsessive-Compulsive Disorder 2 D009771 ClinicalTrials
Back Pain 2 D001416 ClinicalTrials
Cervical Intraepithelial Neoplasia 2 D018290 ClinicalTrials
Uterine Cervical Neoplasms 1 D002583 ClinicalTrials
Myeloproliferative Disorders 1 D009196 ClinicalTrials
Keratosis, Actinic 1 D055623 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Hypotension, Orthostatic 1 D007024 ClinicalTrials
Neuroblastoma 1 D009447 ClinicalTrials
Hepatolenticular Degeneration 1 D006527 ClinicalTrials
Carcinoma, Hepatocellular 1 D006528 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Breast Carcinoma In Situ 1 D000071960 ClinicalTrials
Uterine Cervical Neoplasms 1 D002583 ClinicalTrials
Mouth Neoplasms 1 D009062 ClinicalTrials
Depressive Disorder, Major 0 D003865 ClinicalTrials
Obesity 0 D009765 ClinicalTrials

Related Entries

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Gastrointestinal disorder 36.0
Infections and infestations Infection 27.0
Infections and infestations Infestation 27.0
Gastrointestinal disorders Gastrointestinal disorder 26.0
Infections and infestations Infection 25.0
Infections and infestations Infestation 25.0
Gastrointestinal disorders Gastrointestinal disorder 24.0
Nervous system disorders Nervous system disorder 21.0
Nervous system disorders Headache
Nervous system disorders Headache 20.2
Infections and infestations Infection 20.0
Infections and infestations Infestation 20.0
Musculoskeletal and connective tissue disorders Bone disorder 17.0
Nervous system disorders Nervous system disorder 17.0
Nervous system disorders Headache 16.0
Nervous system disorders Headache 15.8
Nervous system disorders Headache 15.5
Nervous system disorders Headache 15.4
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 15.0
Nervous system disorders Headache 14.5
Nervous system disorders Headache 13.0
Gastrointestinal disorders Dyspepsia 12.8
Vascular disorders Hypertension 12.5
Gastrointestinal disorders Dyspepsia 12.2
Investigations Body temperature increased 11.0
Gastrointestinal disorders Nausea 11.0
Nervous system disorders Nervous system disorder 11.0
Gastrointestinal disorders Vomiting 11.0
Gastrointestinal disorders Dyspepsia 10.9
Gastrointestinal disorders Diarrhoea 10.5
Gastrointestinal disorders Abdominal pain upper 10.0
Musculoskeletal and connective tissue disorders Bone disorder 10.0
Nervous system disorders Headache 10.0
Infections and infestations Infection 9.9
Infections and infestations Upper respiratory tract infection 9.9
Vascular disorders Hypertension
Infections and infestations Infection 9.8
Infections and infestations Upper respiratory tract infection 9.8
Gastrointestinal disorders Diarrhoea 9.3
Gastrointestinal disorders Abdominal pain 9.0
Investigations Body temperature increased 9.0
Gastrointestinal disorders Gastrointestinal pain 9.0
Gastrointestinal disorders Dyspepsia 8.8
Infections and infestations Infection 8.1
Infections and infestations Upper respiratory tract infection 8.1
Gastrointestinal disorders Abdominal pain upper 8.0
Investigations Body temperature increased 8.0
Musculoskeletal and connective tissue disorders Bone disorder 8.0
Respiratory, thoracic and mediastinal disorders Cough 8.0
Gastrointestinal disorders Diarrhoea 8.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 8.0
Gastrointestinal disorders Abdominal pain 7.7
Gastrointestinal disorders Gastrointestinal pain 7.7
Gastrointestinal disorders Abdominal pain 7.0
Musculoskeletal and connective tissue disorders Arthralgia 7.0
Respiratory, thoracic and mediastinal disorders Cough 7.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 7.0
Gastrointestinal disorders Nausea 7.0
Ear and labyrinth disorders Vertigo 7.0
Gastrointestinal disorders Nausea 6.8
Infections and infestations Infection
Infections and infestations Infection 6.7
Gastrointestinal disorders Nausea 6.7
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Dyspepsia
Vascular disorders Hypertension 6.1
Gastrointestinal disorders Abdominal pain upper 6.0
Infections and infestations Nasopharyngitis 6.0
Gastrointestinal disorders Nausea 6.0
Gastrointestinal disorders Vomiting 6.0
Gastrointestinal disorders Diarrhoea 5.8
Infections and infestations Sinusitis 5.8
Gastrointestinal disorders Diarrhoea 5.6
Infections and infestations Sinusitis 5.4
Gastrointestinal disorders Diarrhoea 5.3
Gastrointestinal disorders Nausea
Gastrointestinal disorders Diarrhoea 5.0
Eye disorders Eye disorder 5.0
Infections and infestations Nasopharyngitis 5.0
Infections and infestations Sinusitis 5.0
Gastrointestinal disorders Gastrooesophageal reflux disease 4.7
Infections and infestations Sinusitis
Infections and infestations Sinusitis 4.3
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 4.1
Gastrointestinal disorders Flatulence 4.1
Gastrointestinal disorders Gastrointestinal pain 4.1
Gastrointestinal disorders Abdominal pain 4.0
Musculoskeletal and connective tissue disorders Arthralgia 4.0
Gastrointestinal disorders Diarrhoea 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Gastrointestinal disorders Nausea 4.0
Infections and infestations Sinusitis 4.0
Gastrointestinal disorders Diarrhoea
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Flatulence 3.6
Gastrointestinal disorders Flatulence 3.5
Gastrointestinal disorders Nausea 3.5
Cardiac disorders Oedema peripheral 3.5
Gastrointestinal disorders Nausea 3.4
Gastrointestinal disorders Vomiting 3.2
Gastrointestinal disorders Gastrooesophageal reflux disease
Musculoskeletal and connective tissue disorders Arthralgia 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Gastrointestinal disorders Vomiting 3.0
Nervous system disorders Cerebrovascular accident 2.98
Nervous system disorders Insomnia 2.9
Gastrointestinal disorders Abdominal pain
Musculoskeletal and connective tissue disorders Back pain 2.8
Cardiac disorders Dyspnoea 2.8
Gastrointestinal disorders Gastrointestinal pain
Musculoskeletal and connective tissue disorders Back pain 2.6
Cardiac disorders Dizziness 2.6
Gastrointestinal disorders Pharyngitis 2.6
Nervous system disorders Cerebrovascular accident 2.48
Infections and infestations Rhinitis 2.4
Cardiac disorders Dizziness 2.3
Nervous system disorders Insomnia
Nervous system disorders Insomnia 2.3
Gastrointestinal disorders Pharyngitis 2.3
Infections and infestations Rhinitis 2.3
Nervous system disorders Cerebrovascular accident 2.25
Musculoskeletal and connective tissue disorders Back pain 2.2
Skin and subcutaneous tissue disorders Dermatitis 2.2
Gastrointestinal disorders Flatulence 2.2
Skin and subcutaneous tissue disorders Rash 2.2
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 2.1
Cardiac disorders Oedema peripheral 2.1
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 2.1
Gastrointestinal disorders Vomiting
Cardiac disorders Dizziness 2.0
Infections and infestations Rhinitis 2.0
Nervous system disorders Cerebrovascular accident
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.7
Gastrointestinal disorders Pharyngitis 1.7
Cardiac disorders Dyspnoea
Gastrointestinal disorders Pharyngitis 1.6
Nervous system disorders Insomnia 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.3
Cardiac disorders Dizziness 1.3
Nervous system disorders Insomnia 1.3
Skin and subcutaneous tissue disorders Rash 1.3
Infections and infestations Rhinitis
Infections and infestations Rhinitis 1.3
Skin and subcutaneous tissue disorders Dermatitis 1.2
Skin and subcutaneous tissue disorders Rash 1.2
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 1.1
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 1.1
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Flatulence
Cardiac disorders Oedema peripheral 1.0
Ear and labyrinth disorders Vertigo 1.0
Musculoskeletal and connective tissue disorders Back pain 0.9
Nervous system disorders Cerebrovascular accident
Infections and infestations Rhinitis 0.6
Cardiac disorders Cardiac failure 0.5
Cardiac disorders Cardiac failure 0.3
Vascular disorders Cerebrovascular disorder 0.3
Vascular disorders Deep vein thrombosis 0.3
Cardiac disorders Angina pectoris 0.2
Vascular disorders Angina unstable 0.2
Cardiac disorders Cardiac failure 0.2
Vascular disorders Deep vein thrombosis 0.2
Cardiac disorders Angina pectoris 0.1
Vascular disorders Angina unstable 0.1
Cardiac disorders Cardiac failure 0.1
Vascular disorders Cerebrovascular disorder 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
18.54
Musculoskeletal and connective tissue disorders
12.46
Nervous system disorders
8.15
Gastrointestinal disorders
7.82
Immune system disorders
7.65
Injury, poisoning and procedural complications
6.94
Skin and subcutaneous tissue disorders
5.42
Vascular disorders
4.94
Respiratory, thoracic and mediastinal disorders
4.36
Cardiac disorders
3.93
Psychiatric disorders
3.53
Infections and infestations
3.22
Investigations
3.02

Cross References

Resources Reference
CAS NUMBER 169590-42-5
ChEBI 41423
ChEMBL CHEMBL118
DrugBank DB00482
DrugCentral 568
EPA CompTox DTXSID0022777
FDA SRS JCX84Q7J1L
Human Metabolome Database HMDB0005014
Guide to Pharmacology 2892
KEGG C07589
PDB CEL
PharmGKB PA448871
PubChem 2662
SureChEMBL SCHEMBL3708
ZINC ZINC000002570895
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