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Encyclopedia > Phenacetin
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) (decomposes)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Phenacetin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

Phenacetin, introduced in 1887, was used principally as an analgesic, and was the first fever reducer to go on the market. 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 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. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... 1887 (MDCCCLXXXVII) is a common year starting on Saturday (click on link for calendar) of the Gregorian calendar or a common year starting on Monday of the Julian calendar. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... An inotrope is an agent which increases or decreases the force or energy of muscular contractions. ... Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ... Rheumatoid arthritis (RA) is traditionally considered a chronic, inflammatory autoimmune disorder that causes the immune system to attack the joints. ... The abdominal cutaneous nerve entrapment syndrome (ACNES) consists of pain caused by entrapment of the abdominal segmental nerves within the rectus abdominis muscle. ... For other uses, see Ataxia (disambiguation). ...


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. Animal model refers to a non-human animal with a disease that is similar to a human condition. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... Transitional cell carcinoma is a type of cancer that originates in the kidney, bladder or ureter. ... The renal pelvis represents the dilated proximal part of the ureter. ... Glucose-6-phosphate dehydrogenase (G6PD) deficiency is an X-linked recessive hereditary disease featuring nonimmune hemolytic anemia in response to a number of causes. ... {{otheruses4|1=medical hemoglobin]] into the surrounding fluid (plasma, in vivo). ... IGM might be an acronym or abbreviation for: The polymeric immunoglobulin, IgM International Grandmaster, a chess ranking intergalactic medium Intragroup medium - see: Intracluster medium IG Metall - the dominant German metalworkers union IGM is an acronym created by Robinson Technologies for several early BBS door games, including Legend of the Red... Human red blood cells Red blood cells are the most common type of blood cell and are the vertebrate bodys principal means of delivering oxygen to body tissues via the blood. ... Look up Complement in Wiktionary, the free dictionary. ...


Synthesis (Northern Kentucky University)


ETHER SYNTHESIS: CONVERSION OF ACETAMINOPHEN INTO PHENACETIN Required Pre-lab readings: Ege, 5th Ed., sect 13.4, pp 498-501; Morhig, Chapter 19. Techniques you must be prepared to use: reflux; extraction; rotary evaporation; recrystallization. In the reaction today you will be converting 4-acetamidophenol (Acetaminophen) into ethyl 4- acetamidophenyl ether (Phenacetin). Both compounds are ingredients in many over-the-counter analgesics. This reaction is an example of the Williamson ether synthesis. For most ether syntheses strong bases such as amide ion are necessary to generate the nucleophile.


In a 50 mL round-bottomed flask place 12 mmol of liquid ethyl iodide, 15 mL of methyl ethyl ketone (2-butanone; MEK) as solvent, Acetaminophen (1.5 g; ?? mmol.), and powered anhydrous K2CO3 (2.5 g; ?? mmol). Mechanically stir this mixture and reflux for 1 hour. After the reflux is complete cool the flask in an ice/water bath and gravity filter the contents into a separatory funnel. Use small amounts of ether to insure that you have quantitatively transferred all the organic material from the flask to the funnel. Wash the organic phase with 5% aq. NaOH (what is the purpose of this step?), then dry it (Na2SO4) and decant into a flask and remove the solvents by rotary evaporation. The product is purified by recrystallization from water. Allow the purified product to air dry.


Phenacetin was widely used until the third quarter of the twentieth century, but was then largely replaced by non-carcinogenic drugs. Some branded phenacetin-based preparations continued to be sold, but with the phenacetin replaced by safer alternatives. A popular brand of phenacetin was Roche's Saridon, which was reformulated in 1983 to contain propyphenazone, paracetamol and caffeine. Paracetamol is a metabolite of phenacetin with similar analgesic and antipyretic effects, but the new formulation has not been found to have phenacetin's carcinogenicity. Hoffmann-La Roche, Ltd. ... Saridon is an analgesic combination containing 150 mg of propyphenazone, 250 mg of paracetamol and 50 mg of caffeine. ... Year 1983 (MCMLXXXIII) was a common year starting on Saturday (link displays the 1983 Gregorian calendar). ... Propyphenazone or Isopropylantipyrine (C14H18N2O, 1,2-dihydro-1,5-dimethyl-4-(isopropyl)-2-phenyl-pyrazol-3-one) is a metabolite of phenacetin with similar analgesic and antipyretic effects. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN), is the active metabolite of phenacetin, a so-called coal tar analgesic. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ...


Connection between chronic phenacetin use and renal papillary necrosis

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. Renal papillary necrosis is a form of nephropathy involving the death (necrosis) of the renal papilla. ... In the kidney, the renal papilla is the location where the kidneys converge at a traffic intersection. ...


Use as a filler for illegal cocaine

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] A cutting agent is a chemical used to cut (adulterate) illicit drugs with something less expensive than the drug itself. ... Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. ...


Notes and references

  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. ^ "Cancer chemical in street cocaine", BBC News, 23 November 2006. 
  • Carcinogen report from the NIH
  • Safety (MSDS) data for phenacetin

  Results from FactBites:
 
AllRefer Health - Analgesic Nephropathy (Nephropathy - Analgesic, Phenacetin Nephritis) (609 words)
It is usually a result of prolonged or chronic ingestion of analgesics, especially over-the-counter (OTC) medications that contain phenacetin or acetaminophen and nonsteroidal antiinflammatory drugs (NSAIDs) including aspirin or ibuprofen.
The incidence has decreased significantly since phenacetin is no longer widely available in OTC preparations.
Risk factors include use of OTC analgesics containing more than one active ingredient, chronic headache, chronic backache or musculoskeletal pain, pain with menstrual periods, emotional and/or behavioral changes, and history of dependent behaviors including smoking, alcoholism, and excessive use of tranquilizers.
Phenacetin and Analgesic Mixtures containing Phenacetin (IARC Summary & Evaluation, Supplement7, 1987) (774 words)
Phenacetin given orally induced benign and malignant tumours of the urinary tract in mice [ref: 20] and rats [ref: 1,21] and of the nasal cavity in rats [ref: 1].
In rats, phenacetin alone or in combination with phenazone slightly increased the incidences of renal-cell and renal-pelvic tumours; rats treated with phenacetin, phenazone and caffeine in combination developed hepatomas [ref: 22].
Phenacetin was mutagenic to bacteria when tested in the presence of a metabolic system derived from hamster but not mouse or rat liver.
  More results at FactBites »

 
 

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