Phenacetin

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Phenacetin
Systematic (IUPAC) name
N-(4-ethoxyphenyl)ethanamide
Identifiers
CAS number 62-44-2
ATC code N02BE03
PubChem 4754
DrugBank EXPT03306
Chemical data
Formula C10H13NO2 
Mol. mass 179.216 g/mol
Physical data
Melt. point 134-136 °C (-79 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

Phenacetin, introduced in 1887, is used principally as an analgesic. Typical doses of 300mg to 500mg a day result in an analgesic effect. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action of the heart, where it acts as a negative inotrope. It also is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type), intercostal neuralgia, and some forms of ataxia.

Phenacetin, and products containing phenacetin have been shown in an animal model to be carcinogenic. In humans, many case reports have implicated products containing phenacetin in urothelial neoplasms, especially transitional cell carcinoma of the renal pelvis. In one prospective series, phenacetin was associated with an increased risk of death due to urologic or renal diseases, death due to cancers, and death due to cardiovascular diseases.[1] In addition, people with glucose-6-phosphate dehydrogenase deficiency may experience acute hemolysis while taking this drug. Acute hemolysis is possible in the case of patients who develop an IgM response to Phenacetin leading to immune complexes that bind to erythrocytes in blood. The erythrocytes are then lysed when the complexes activate the complement cascade.

The most popular brand of phenacetin was Roche's Saridon. Due to its carcinogenic properties and a link to analgesic-induced nephropathy, Saridon was reformulated in 1983. The new formulation contains propyphenazone, paracetamol and caffeine. Both propyphenazone and paracetamol are metabolites of phenacetin with similar analgesic and antipyretic effects. The new formulation has not been shown to share phenacetin's carcinogenic side-effects.

Contents

Chronic use of phenacetin is known to lead to renal papillary necrosis.[2][3][4] This is a condition which results in destruction of some or all of the renal papillae in the kidneys.

Phenacetin is now being widely used as a cutting agent to adulterate illegally supplied cocaine due to the similar physical features of the two drugs. [5]

  1. ^ Dubach U, Rosner B, Stürmer T (1991). "An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987)". N Engl J Med 324 (3): 155-60. PMID 1984193. 
  2. ^ Cochran A, Lawson D, Linton A (1967). "Renal papillary necrosis following phenacetin excess.". Scott Med J 12 (7): 246-50. PMID 6036245. 
  3. ^ Tan G, Rabbino M, Hopper J (1964). "Is Phenacetin a Nephrotoxin? A Report on Twenty-three Users of the Drug.". Calif Med 101: 73-7. PMID 14180501. 
  4. ^ Brix A. "Renal papillary necrosis.". Toxicol Pathol 30 (6): 672-4. PMID 12512867. 
  5. ^ BBC News report, "Cancer chemical in street cocaine", 23 November 2006

v • d • e
Analgesics (N02A, N02B)
Opioids Bezitramide, Buprenorphine, Butorphanol, Dextromoramide, Dextropropoxyphene, Diamorphine, Dihydrocodeine, Fentanyl, Hydromorphone, Ketobemidone, Methadone, Morphine, Nalbufine, Nicomorphine, Opium, Oxycodone, Papaveretum, Pethidine, Piritramide, Tramadol (see also longer list)
Salicylic acid and derivatives Aspirin (Acetylsalicylic Acid), Diflunisal, Ethenzamide -- See also: NSAIDs
Pyrazolones Aminophenazone, Metamizole, Phenazone
Anilides Paracetamol (acetaminophen), Phenacetin
Others Ziconotide, Tetrahydrocannabinol, Ibuprofen, Ketoprofen, Mefenamic Acid, Naproxen, Diclofenac, Flurbiprofen, Diflunisal, Fenoprofen, Indomethacin, Ketorolac, Meclofenamate, Meloxicam, Piroxicam, Tolmetin
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