Diflunisal

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Image:Diflunisal-2D-skeletal.png
Diflunisal
Systematic (IUPAC) name
5-(2,4-difluorophenyl)-2-hydroxy-benzoic acid
Identifiers
CAS number	22494-42-4
ATC code	N02BA11
PubChem	3059
DrugBank	APRD00922
Chemical data
Formula	C₁₃H₈F₂O₃
Mol. mass	250.198 g/mol
Pharmacokinetic data
Bioavailability	80-90%
Protein binding	>99%
Metabolism	Hepatic
Half life	8 to 12 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) C(US)
Legal status	POM(UK) ℞-only(US)
Routes	Oral

Diflunisal is a generic NSAID (non-steroidal anti-inflammatory drug). It is often used under the brand name Dolobid marketed by Merck & Co. Diflunisal acts by inhibiting the production of prostaglandin, a hormone that creates inflammation and stimulates the neuro receptors for pain. Though diflunisal has an onset of 1 hour, and maximum analgesia at 2 to 3 hours, the diflunisal plasma levels will not be steady until repeated doesages are achieved. To increase the rate at which the diflunisal plasma levels become steady, a loading dose is usually used. It is primarily used to treat symptoms of arthritis.

Overdose

Deaths that have occurred from diflunisal usually involved mixed drugs and or extremely high dosages. The oral LD₅₀ is 500 mg/kg. Symptoms of overdose include, coma, tachycardia, stupor, and vomiting. The lowest dose without the presence of other medicines which caused death was 15 grams. Mixed with other medicines, a death at 7.5 grams has also occurred. Diflunisal usually comes in 250 or 500 mg, thus it is relatively hard to overdose by accident.

Abuse

This medication has no side effects like those of recreational drugs.

Indicated for:

Pain, mild-moderate
Osteoarthritis
Rheumatoid arthritis
Injury to tendons
Inflammation

Do not cut/crush/chew. Monitor blood pressure. Use lowest effective dose for shortest duration.

Side effects:

Cardiovascular:

Irregular heart beat (!)
This medication may increase risk of serious and potentially fatal cardiovascular thrombotic events, MI, and stroke (!)
Risk may increase with duration of use (!)
Increased risk for Cardiovascular disease history (!)
Contraindicated for Heart Bypass peri-op pain (!)

Ear, nose, and throat:

Ringing in the ears (!)

Eye:

Yellowing of eyes (!)

Gastrointestinal:

Increased risk of serious GI adverse events including bleeding, ulceration, and stomach or intestine perforation which can be fatal: may occur at any time during use and without warning. Elderly at greater risk for serious GI events (!)
Abdominal pain and cramps
Constipation
Gas & Flatulence
Diarrhea
Nausea & Vomiting
Dyspepsia

Central Nervous System:

Drowsiness
Dizziness
Headache
Insomnia
Fatigue
Somnolence

Psychiatric:

Nervousness

Skin:

Swelling of the feet, ankles, lower legs, and hands (!)
Yellowing of skin (!)
Rash
Ecchymosis

Contraindications:

Hypersensitivity to aspirin/NSAID-induced asthma or urticaria
Aspirin triad
Pregnancy 3rd trimester
CABG surgery (peri-op pain)

Cautions:

Cardiovascular disease
Cardiac risk factors
Hypertension
Congestive Heart Failure
Elderly or debilitated
Impaired liver function
Impaired kidney function
Dehydration
Fluid retention
GI bleed history/PUD
Asthma
Coagulopathy
Smoker

Corticosteriod use
Anticoagulant use
Alcohol use
Diuretic use
ACE Inhibitor use

Prolonged use

Precautions:

If symptoms labeled, (!), appear, stop usage immediately and contact your doctor.
Overdose is possible and deaths have occurred.
Do not take while on other pain medications.
Do not take while pregnant or breast feeding.

External links

http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a684037.html
http://www.medsafe.govt.nz/Profs/Datasheet/discontinued/ansaltab.htm
Dolobid Prescribing Information (manufacturer's website)
Dolobid Medication Guide (manufacturer's website)
Diflunisal (patient information)

v • d • e Non-steroidal anti-inflammatory drug (NSAID) products (primarily M01A and M02A, also N02BA)
Salicylates	Aspirin (acetylsalicylic acid) · Aloxiprin · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Methyl salicylate · Salsalate · Salicin · Salicylamide · Sodium salicylate
Arylalkanoic acids	Diclofenac · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Etodolac · Indometacin · Indomethacin farnesil · Nabumetone · Oxametacin · Proglumetacin · Sulindac · Tolmetin
2-Arylpropionic acids (profens)	Ibuprofen · Alminoprofen · Benoxaprofen · Carprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuproxam · Indoprofen^† · Ketoprofen · Ketorolac · Loxoprofen · Miroprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tarenflurbil · Tiaprofenic acid
N-Arylanthranilic acids (fenamic acids)	Mefenamic acid · Flufenamic acid · Meclofenamic acid · Tolfenamic acid
Pyrazolidine derivatives	Phenylbutazone · Ampyrone · Azapropazone · Clofezone · Kebuzone · Metamizole^† · Mofebutazone · Oxyphenbutazone · Phenazone · Sulfinpyrazone
Oxicams	Piroxicam · Droxicam · Lornoxicam · Meloxicam · Tenoxicam
COX -2 inhibitors	Celecoxib · Deracoxib^‡ · Etoricoxib · Firocoxib^‡ · Lumiracoxib^† · Parecoxib · Rofecoxib^† · Valdecoxib^†
Sulphonanilides	Nimesulide
Topically used products	Bendazac · Diclofenac · Etofenamate · Felbinac · Flurbiprofen · Ibuprofen · Indometacin · Ketoprofen · Naproxen · Piroxicam · Suprofen
Others	Fluproquazone · COX-inhibiting nitric oxide donator
Items listed in bold indicate initially developed compounds of specific groups. ^†Withdrawn drugs. ^‡Veterinary use medications.