VALDECOXIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2001) Withdrawn (2004)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: M01AH03
UNII: 2919279Q3W

Structure
InChI Key LNPDTQAFDNKSHK-UHFFFAOYSA-N
Smile Cc1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1
InChI
InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14N2O3S
Molecular Weight 314.37
AlogP 2.96
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 86.19
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase-2 inhibitor
Primary Target
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Lyase
- 43-4574 - 43-43000 -
Enzyme Oxidoreductase
- 5-660 - - 37-98
Enzyme Transferase
- - - - 6.971-26.26
Enzyme
- 5-660 - 43-43000 37-98
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 2.21-7
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 2927 - 2903 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 120.37
Transporter Primary active transporter Oxidoreduction-driven transporters
- 1100 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Pharyngitis 3 D010612 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Pancreatitis 2 D010195 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Abdominal pain 17.0
Gastrointestinal disorders Gastrointestinal pain 17.0
Gastrointestinal disorders Dyspepsia 15.0
Gastrointestinal disorders Dyspepsia 13.4
Gastrointestinal disorders Dyspepsia 12.9
Gastrointestinal disorders Diarrhoea 10.8
Gastrointestinal disorders Abdominal pain 10.1
Gastrointestinal disorders Gastrointestinal pain 10.1
Gastrointestinal disorders Nausea 8.7
Gastrointestinal disorders Nausea 8.4
Gastrointestinal disorders Abdominal pain 8.2
Gastrointestinal disorders Gastrointestinal pain 8.2
Gastrointestinal disorders Dyspepsia 7.9
Gastrointestinal disorders Flatulence 7.7
Gastrointestinal disorders Nausea 7.7
Nervous system disorders Headache
Gastrointestinal disorders Abdominal pain 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Gastrointestinal disorders Nausea 7.0
Infections and infestations Upper respiratory tract infection 6.7
Nervous system disorders Headache 6.6
Infections and infestations Upper respiratory tract infection 6.4
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Upper respiratory tract infection 6.3
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Nausea
Nervous system disorders Headache 5.5
Gastrointestinal disorders Diarrhoea 5.4
Gastrointestinal disorders Flatulence 5.4
Nervous system disorders Headache 4.8
Gastrointestinal disorders Diarrhoea 4.7
Nervous system disorders Headache 4.3
Infections and infestations Upper respiratory tract infection 4.3
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness 4.2
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Diarrhoea 3.9
Cardiac disorders Dizziness 3.4
Infections and infestations Sinusitis 3.4
Cardiac disorders Oedema peripheral 3.2
Gastrointestinal disorders Flatulence 3.1
General disorders and administration site conditions Influenza like illness 3.1
Gastrointestinal disorders Abdominal distension 3.0
Gastrointestinal disorders Abdominal distension 2.9
Gastrointestinal disorders Flatulence 2.9
General disorders and administration site conditions Influenza like illness 2.9
Cardiac disorders Oedema peripheral 2.9
Musculoskeletal and connective tissue disorders Back pain 2.8
Cardiac disorders Dizziness 2.7
Cardiac disorders Dizziness 2.6
Infections and infestations Sinusitis 2.6
Gastrointestinal disorders Abdominal distension 2.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.4
Musculoskeletal and connective tissue disorders Myalgia 2.4
Cardiac disorders Oedema peripheral 2.4
General disorders and administration site conditions Influenza like illness
Infections and infestations Sinusitis
Gastrointestinal disorders Abdominal distension 2.1
Cardiac disorders Dizziness
Cardiac disorders Oedema peripheral 2.1
Gastrointestinal disorders Abdominal distension
General disorders and administration site conditions Influenza like illness 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 1.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Skin and subcutaneous tissue disorders Dermatitis 1.5
Skin and subcutaneous tissue disorders Rash 1.5
Musculoskeletal and connective tissue disorders Back pain 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.4
Musculoskeletal and connective tissue disorders Myalgia 1.4
Skin and subcutaneous tissue disorders Rash 1.4
Infections and infestations Sinusitis 1.1
Musculoskeletal and connective tissue disorders Back pain 1.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Cardiac disorders Oedema peripheral
Skin and subcutaneous tissue disorders Dermatitis 0.5
Skin and subcutaneous tissue disorders Rash 0.5

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Eye disorders
19.54
Nervous system disorders
17.24
Vascular disorders
13.79
Skin and subcutaneous tissue disorders
9.2
General disorders and administration site conditions
5.75
Immune system disorders
5.75
Gastrointestinal disorders
4.6
Cardiac disorders
3.45
Psychiatric disorders
3.45
Respiratory, thoracic and mediastinal disorders
3.45
Infections and infestations
2.3
Injury, poisoning and procedural complications
2.3
Investigations
2.3
Metabolism and nutrition disorders
2.3
Renal and urinary disorders
2.3

Cross References

Resources Reference
CAS NUMBER 181695-72-7
ChEBI 63634
ChEMBL CHEMBL865
DrugBank DB00580
DrugCentral 2799
EPA CompTox DTXSID6044226
FDA SRS 2919279Q3W
Human Metabolome Database HMDB05033
Guide to Pharmacology 2894
KEGG D02709
PDB COX
PharmGKB PA10226
PubChem 119607
SureChEMBL SCHEMBL3356
ZINC ZINC000000006694
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