Diclofenac Acid
M01A - NSAIDs and antirheumatic products, non-steroids
ATC M01AB05
Small molecule
approved 1988
Oral
Parenteral
Topical
Natural product
Black-box warning
JFDA label: Tratul Cap
⚠ Black-Box Warning
- neurotoxicity — ChEMBL drug_warning (Black Box Warning) | United States
- gastrointestinal toxicity — ChEMBL drug_warning (Black Box Warning) | United States
- cardiotoxicity — ChEMBL drug_warning (Black Box Warning) | United States
Mechanism of Action
Inhibitor of Cyclooxygenase — Cyclooxygenase inhibitor
| Target | Action | Gene / class |
|---|
| Cyclooxygenase efficacy |
INHIBITOR |
|
Indications
Approved
- Acute Pain — pain
- Arthralgia — Arthralgia
- Arthritis, Rheumatoid — rheumatoid arthritis
- Cataract — cataract
- Dysmenorrhea — Dysmenorrhea
- Eye Diseases — eye inflammation
- Inflammation — inflammation
- Keratosis, Actinic — actinic keratosis
- Migraine Disorders — migraine disorder
- Myalgia — Myalgia
- Osteoarthritis — osteoarthritis
- Rheumatic Diseases — rheumatic disease
- Sprains and Strains — sprain
Off-label
- Bile Duct Diseases
- Carcinoma
- Carcinoma, Basal Cell
- Infertility
- Mastodynia
- Osteoarthritis, Hip
- Osteoarthritis, Knee
- Pulmonary Embolism
- Renal Colic
- Spondylitis, Ankylosing
- Stomach Ulcer
- Toothache
- Wounds and Injuries
Pregnancy & Lactation
Chemistry & Properties
| Formula | C14H11Cl2NO2 |
|---|
| Molecular weight | 296.15 g/mol |
|---|
| IUPAC name | 2-[2-(2,6-dichloroanilino)phenyl]acetic acid |
|---|
| CAS | 15307-86-5 |
|---|
| PubChem CID | 3033 |
|---|
| InChIKey | DCOPUUMXTXDBNB-UHFFFAOYSA-N |
|---|
| logP | 4.36 (XLogP 4.4) |
|---|
| Polar surface area | 49.33 Ų |
|---|
| H-bond acceptors / donors | 2 / 2 |
|---|
| Drug-likeness (QED) | 0.88 |
|---|
| Lipinski violations | 0 |
|---|
SMILES
O=C(O)Cc1ccccc1Nc1c(Cl)cccc1ClBiology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | No (logBB -1.3) |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|
| CYP1A2 | Substrate |
— |
| CYP2B6 | Substrate |
— |
| CYP2C19 | Substrate |
— |
| CYP2C9 | Inhibitor |
— |
| CYP2C9 | Substrate |
— |
| CYP3A4 | Substrate |
— |
Receptor binding (top 4)
| Target | Action | Affinity |
|---|
| COX-1 (PTGS1) |
Inhibitor |
pIC50 7.9 |
| COX-2 (PTGS2) |
Inhibitor |
pIC50 7.7 |
| Peroxisome proliferator-activated receptor-γ (PPARG) |
Antagonist |
pKi 6.2 |
| TRPM3 (TRPM3) |
Channel blocker |
pIC50 5.2 |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)
Registered Products (1)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|
| Tratul Cap
|
Capsule 50 mg |
20 cap |
Kurdi Drug Store |
4.590 |