| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H11Cl2NO2 |
| Molecular Weight | 296.149 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=C(NC2=C(Cl)C=CC=C2Cl)C=CC=C1
InChI
InChIKey=DCOPUUMXTXDBNB-UHFFFAOYSA-N
InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
| Molecular Formula | C14H11Cl2NO2 |
| Molecular Weight | 296.149 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Diclofenac is a nonsteroidal anti-inflammatory drug (NSAID) of the phenylacetic acid class with anti-inflammatory, analgesic, and antipyretic properties. Contrary to the action of many traditional NSAIDs, diclofenac inhibits cyclooxygenase (COX)-2 enzyme with greater potency than it does COX-1. In addition diclofenac can inhibit the thromboxane-prostanoid receptor, affect arachidonic acid release and uptake, inhibit lipoxygenase enzymes, and activate the nitric oxide-cGMP antinociceptive pathway. Other novel mechanisms of action may include the inhibition of substrate P, inhibition of peroxisome proliferator activated receptor gamma (PPARgamma), blockage of acid-sensing ion channels, alteration of interleukin-6 production, and inhibition of N-methyl-D-aspartate (NMDA) receptor hyperalgesia. Similar to other NSAIDs, diclofenac is associated with serious dose-dependent gastrointestinal, cardiovascular, and renal adverse effects. Since its introduction in 1973, a number of different diclofenac-containing drug products have been developed with the goal of improving efficacy, tolerability, and patient convenience. Delayed- and extended-release forms of diclofenac sodium were initially developed with the goal of improving the safety profile of diclofenac and providing convenient, once-daily dosing for the treatment of patients with chronic pain. New drug products consisting of diclofenac potassium salt were associated with faster absorption and rapid onset of pain relief. These include diclofenac potassium immediate-release tablets, diclofenac potassium liquid-filled soft gel capsules, and diclofenac potassium powder for oral solution. The advent of topical formulations of diclofenac enabled local treatment of pain and inflammation while minimizing systemic absorption of diclofenac. SoluMatrix diclofenac, consisting of submicron particles of diclofenac free acid and a proprietary combination of excipients, was developed to provide analgesic efficacy at reduced doses associated with lower systemic absorption. The drug's likely impact on the Asian vulture population was widely reported. The dramatic mortality was attributed largely to renal failure caused by exposure to diclofenac in livestock carcasses on which the birds fed. Although not the most endearing species, vultures are important environmental scavengers and, since veterinary use of diclofenac was stopped in the region in 2006, the decline in vulture numbers has slowed.
CNS Activity
Originator
Approval Year
AUC
T1/2
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Patents
Sample Use Guides
For topical dosage form (gel):
For actinic keratosis using Solaraze® 3% gel:
Adults—Apply to affected skin area two times a day.
Children—Use and dose must be determined by your doctor.
For osteoarthritis of the hands, elbows, or wrists using Voltaren® 1% gel:
Adults—Apply 2 grams to the affected skin areas four times a day (a total of 8 grams each day). However, the total dose should not exceed 32 grams per day over all affected joints. Use the enclosed dosing card to measure the appropriate dose.
Children—Use and dose must be determined by your doctor.
For osteoarthritis of the knees, ankles, or feet using Voltaren® 1% gel:
Adults—Apply 4 grams to the affected skin areas four times a day (a total of 16 grams each day). However, the total dose should not exceed 32 grams per day over all affected joints. Use the enclosed dosing card to measure the appropriate dose.
Children—Use and dose must be determined by your doctor.
For topical dosage form (solution):
For osteoarthritis of the knee:
Adults—40 drops (10 drops at a time) on each affected knee four times a day.
Children—Use and dose must be determined by your doctor.
For transdermal dosage form (skin patch):
For acute pain:
Adults—One patch applied to the painful area two times a day.
Children—Use and dose must be determined by your doctor.
For oral dosage form (capsules):
For acute pain:
Adults—18 or 35 milligrams (mg) three times a day.
Children—Use and dose must be determined by your doctor.
For osteoarthritis:
Adults—35 milligrams (mg) three times a day.
Children—Use and dose must be determined by your doctor.
For oral dosage forms (delayed-release tablets, enteric-coated tablets):
For ankylosing spondylitis:
Adults—25 milligrams (mg) four times a day, with an extra 25 mg dose at bedtime if necessary.
Children—Use and dose must be determined by your doctor.
For osteoarthritis:
Adults—50 milligrams (mg) two or three times a day, or 75 mg two times a day.
Children—Use and dose must be determined by your doctor.
For rheumatoid arthritis:
Adults—50 milligrams (mg) three or four times a day, or 75 mg two times a day.
Children—Use and dose must be determined by your doctor.
For oral dosage form (immediate-release tablets):
For osteoarthritis:
Adults—50 milligrams (mg) two or three times a day.
Children—Use and dose must be determined by your doctor.
For pain or menstrual cramps:
Adults—50 milligrams (mg) three times a day. Your doctor may direct you to take 100 mg for the first dose only.
Children—Use and dose must be determined by your doctor.
For rheumatoid arthritis:
Adults—50 milligrams (mg) three or four times a day.
Children—Use and dose must be determined by your doctor.
For oral dosage form (solution):
For migraine headaches:
Adults—One packet (50 milligrams) as a single, one time dose.
Children—Use and dose must be determined by your doctor.
Route of Administration:
Other
Acute (24 h) diclofenac toxicity in a range of (10-1000 μM) concentrations was assesed in primary human hepatocytes. The chronic (9 repeated doses) toxicity at one clinically relevant and another higher concentration (6.4 and 100 μM) was also tested. Acute 24 h assessment revealed toxicity only for the highest tested concentration (1 mM). Upon repeated dose exposure, toxic effects were observed even at a low, clinically relevant concentration (6.4 μM).
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