Systematic (IUPAC) name
Clinical data
Trade names Lopurin, Zyloprim
AHFS/ monograph
MedlinePlus a682673
Pregnancy cat. C(USA)
Legal status -only (US)
Routes tablet (100, 300 mg)
Pharmacokinetic data
Bioavailability 78±20%
Protein binding Negligible
Metabolism hepatic (80% oxypurinol, 10% allopurinol ribosides)
Half-life 2 hours (oxypurinol 18-30 hours)
CAS number 315-30-0 YesY
ATC code M04AA01
PubChem CID 2094
DrugBank DB00437
ChemSpider 2010 YesY
KEGG D00224 YesY
ChEBI CHEBI:40279 YesY
Chemical data
Formula C5H4N4O 
Mol. mass 136.112 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Allopurinol is a drug used primarily to treat hyperuricemia (excess uric acid in blood plasma) and its complications, including chronic gout.[1]


Mechanism of action

Allopurinol is a purine analog; it is a structural isomer of hypoxanthine (a naturally occurring purine in the body) and is an inhibitor of the enzyme xanthine oxidase.[1] Xanthine oxidase is responsible for the successive oxidation of hypoxanthine and xanthine, resulting in the production of uric acid, the product of human purine metabolism.[1] In addition to blocking uric acid production, inhibition of xanthine oxidase causes an increase in hypoxanthine and xanthine, which are converted to closely related purine ribotides adenosine and guanosine monophosphates. Increased levels of these ribotides causes feedback inhibition of amidophosphoribosyl transferase, the first and rate-limiting enzyme of purine biosynthesis. Allopurinol, therefore, decreases both uric acid formation and purine synthesis.


The primary use of allopurinol is to treat hyperuricemia (excess uric acid in blood plasma) and its complications. Allopurinol does not alleviate acute attacks of gout, but is useful in chronic gout to prevent future attacks. Likewise, allopurinol commonly is used as prophylaxis with chemotherapeutic treatments (Ex: mercaptopurine and thioguanine), which can rapidly produce severe hyperuricemia. Other established indications for allopurinol therapy include ischemic reperfusion injury, kidney stones with a uric acid component (uric acid nephrolithiasis), and protozoal infections (Leishmaniasis).

Because allopurinol is not a uricosuric, it can be used in patients with poor kidney function. However, allopurinol has two important disadvantages: Its dosing is complex,[2] and some patients will be hypersensitive to it. Therefore, use of this drug requires careful monitoring.

Allopurinol can be used in patients with poor kidney function, but it may also help them. A study of allopurinol use in patients with chronic kidney disease suggested that "Allopurinol decreases C-reactive protein and slows down the progression of renal disease in patients with chronic kidney disease. In addition, allopurinol reduces cardiovascular and hospitalization risk in these subjects."[3]

A recent study has suggested that allopurinol can help reduce the effects of angina in ischaemic heart disease by reducing the workload on the heart.[4]


Allopurinol is rapidly metabolized by its target, xanthine oxidase, to its active metabolite oxypurinol, which is also an inhibitor of xanthine oxidase. Allopurinol is almost completely metabolized to oxypurinol within two hours of oral administration, whereas oxypurinol is slowly excreted by the kidneys over 18-30 hours. For this reason, oxypurinol is believed to be responsible for the majority of allopurinol's effect.


Side-effects of allopurinol are rare, though significant when they occur. A small percentage of people develop a rash and must discontinue this drug. The most serious adverse effect is a hypersensitivity syndrome consisting of fever, skin rash, eosinophilia, hepatitis, worsened renal function, and, in some cases, allopurinol hypersensitivity syndrome. Allopurinol is one of the drugs commonly known to cause Stevens-Johnson syndrome (SJS) and toxic epidermal necrolysis (TENS), two life-threatening dermatological conditions.

Study finds HLA-B*5801 allele as a genetic marker for severe cutaneous adverse reactions which includes Steven Johnson Syndrome and toxic epidermal necrosis caused by allopurinol.[5]

Allopurinol can cause severe pancytopenia if given with azathioprine or mercaptopurine, due to inhibition of xanthine oxidase, which metabolizes these drugs.

Allopurinol can lower blood pressure in mild hypertension.[6]

It is suspected to cause congenital malformations when used during pregnancy, and should be avoided whenever possible by women trying to conceive.[7]

Brand names

Allopurinol has been marketed in the United States since August 19, 1966, when it was first approved by FDA under the trade name of Zyloprim.[8] Allopurinol was marketed at the time by Burroughs-Wellcome. Allopurinol is now a generic drug sold under a variety of brand names including Allohexal, Allosig, Milurit, Alloril, Progout, Zyloprim, Zyloric, Zyrik and Aluron.[9]


  1. ^ a b c Pacher, P.; Nivorozhkin, A; Szabó, C (2006). "Therapeutic Effects of Xanthine Oxidase Inhibitors: Renaissance Half a Century after the Discovery of Allopurinol". Pharmacological Reviews 58 (1): 87–114. doi:10.1124/pr.58.1.6. PMC 2233605. PMID 16507884. 
  2. ^ Dalbeth, Nicola; Stamp, Lisa (2007). "Allopurinol Dosing in Renal Impairment: Walking the Tightrope Between Adequate Urate Lowering and Adverse Events". Seminars in Dialysis 20 (5): 391–5. doi:10.1111/j.1525-139X.2007.00270.x. PMID 17897242. 
  3. ^ Goicoechea, M.; De Vinuesa, S. G.; Verdalles, U.; Ruiz-Caro, C.; Ampuero, J.; Rincon, A.; Arroyo, D.; Luno, J. (2010). "Effect of Allopurinol in Chronic Kidney Disease Progression and Cardiovascular Risk". Clinical Journal of the American Society of Nephrology 5 (8): 1388–93. doi:10.2215/CJN.01580210. PMC 2924417. PMID 20538833. 
  4. ^ Gout drug 'can prevent angina pain of heart disease', BBC News
  5. ^ Hung, SI; Chung, WH; Liou, LB; Chu, CC; Lin, M; Huang, HP; Lin, YL; Lan, JL et al. (2005). "HLA-B*5801 allele as a genetic marker for severe cutaneous adverse reactions caused by allopurinol". Proceedings of the National Academy of Sciences of the United States of America 102 (11): 4134–9. doi:10.1073/pnas.0409500102. PMC 554812. PMID 15743917. 
  6. ^ Feig, D. I.; Soletsky, B.; Johnson, R. J. (2008). "Effect of Allopurinol on Blood Pressure of Adolescents with Newly Diagnosed Essential Hypertension: A Randomized Trial". JAMA: the Journal of the American Medical Association 300 (8): 924–32. doi:10.1001/jama.300.8.924. Lay summary – Journal Watch (September 3, 2008). 
  7. ^ Kozenko, Mariya; Grynspan, David; Oluyomi-Obi, Titi; Sitar, Daniel; Elliott, Alison M.; Chodirker, Bernard N. (2011). "Potential teratogenic effects of allopurinol: A case report". American Journal of Medical Genetics Part A 155 (9): 2247–52. doi:10.1002/ajmg.a.34139. PMID 21815259. 
  8. ^
  9. ^

Further reading

External links

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Look at other dictionaries:

  • Allopurinol — Général Nom IUPAC 1,2 dihydro 4H pyrazolo[3,4 d]pyrimidin 4 one No CAS …   Wikipédia en Français

  • Allopurinol — Saltar a navegación, búsqueda Estructura química del allopurinol. Allopurinol es un compuesto químico empleado como medicamento frente a la hiperuricemia (exceso de ácido úrico en plasma sanguíneo) y sus complicaciones, como la gota …   Wikipedia Español

  • allopurinol — ● allopurinol nom masculin Médicament qui inhibe la synthèse de l acide urique dans l organisme. (Il est utilisé dans le traitement de la goutte.) …   Encyclopédie Universelle

  • allopurinol — [al′ō pyoor′ə nôl΄, al′ō pyoor′ənōl΄; al΄əpyoor′ə nôl΄, al΄əpyoor′ə nōl΄] n. a white, powdery drug that is an isomer of hypoxanthine and inhibits the production of uric acid: used to treat gout …   English World dictionary

  • Allopurinol — Strukturformel Allgemeines Freiname Allopurinol Andere Namen …   Deutsch Wikipedia

  • allopurinol — /al euh pyoor euh nawl , nol /, n. Pharm. a substance, C5H4N4O, used primarily in the treatment of chronic gout to decrease the synthesis of uric acid. [1960 65; appar. ALLO + PURINE + OL1] * * * ▪ chemical compound       drug used in the… …   Universalium

  • Allopurinol — Al|lo|pu|ri|nol [↑ allo (1), ↑ Purin u. ↑ ol (1)]; das; s: Freiname für einen als Hemmstoff der ↑ Xanthin Oxidase u. als ↑ Urikostatikum bei Gicht eingesetzten Purin Antimetaboliten. * * * Allopurinol …   Universal-Lexikon

  • allopurinol — Inhibitor of xanthine oxidase to inhibit uric acid formation; used in the treatment of gout and to retard the rapid metabolic degradation of 6 mercaptopurine. * * * al·lo·pu·ri·nol …   Medical dictionary

  • allopurinol — noun Etymology: all + purine + 1 ol Date: 1964 a drug C5H4N4O used to promote excretion of uric acid …   New Collegiate Dictionary

  • allopurinol — (= 4 hydroxypyrazolo (3,4 d) pyrimidine) A xanthine oxidase inhibitor used in the treatment of gout …   Dictionary of molecular biology

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