Organic compound
Uric acid
|
![](//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Fluorescent_uric_acid.JPG/180px-Fluorescent_uric_acid.JPG)
Crystals of urate in polarized light
|
Names
|
Preferred IUPAC name
7,9-Dihydro-1
H
-purine-2,6,8(3
H
)-trione
|
Other names
2,6,8-Trioxypurine; 2,6,8-Trihydroxypurine; 2,6,8-Trioxopurine; 1
H
-Purine-2,6,8-trione
|
Identifiers
|
|
|
|
|
3DMet
|
|
|
156158
|
ChEBI
|
|
ChEMBL
|
|
ChemSpider
|
|
DrugBank
|
|
ECHA InfoCard
|
100.000.655
|
EC Number
|
|
|
|
KEGG
|
|
MeSH
|
Uric+Acid
|
|
|
UNII
|
|
|
|
InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h5,12H,(H,9,10)(H,7,8,11)
N
Key: DZGSAURIFGGOJK-UHFFFAOYSA-N
N
|
lactam
form: O=C1Nc2nc(=O)nc2C(=O)N1
intermediate form: Oc0nc(O)nc1c0NC(=O)N1
lactim
form: Oc0nc(O)nc1c0N=C(O)N1
urate monoanion: Oc0nc(O)nc1c0N=C([O-])N1
|
Properties
|
|
C
5
H
4
N
4
O
3
|
Molar mass
|
168.112
g·mol
?1
|
Appearance
|
White crystals
|
Melting point
|
300 °C (572 °F; 573 K)
|
|
6 mg/100 mL (at 20 °C)
|
log
P
|
?1.107
|
Acidity
(p
K
a
)
|
5.6
|
Basicity
(p
K
b
)
|
8.4
|
|
?6.62
×
10
?5
cm
3
mol
?1
|
Thermochemistry
|
|
166.15 J K
?1
mol
?1
(at 24.0 °C)
|
|
173.2 J K
?1
mol
?1
|
|
?619.69 to ?617.93 kJ mol
?1
|
|
?1921.2 to ?1919.56 kJ mol
?1
|
Except where otherwise noted, data are given for materials in their
standard state
(at 25 °C [77 °F], 100 kPa).
|
Chemical compound
Uric acid
is a
heterocyclic compound
of
carbon
,
nitrogen
,
oxygen
, and
hydrogen
with the
formula
C
5
H
4
N
4
O
3
. It forms ions and salts known as
urates
and
acid urates
, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown of
purine
nucleotides
, and it is a normal component of
urine
[1]
.
High blood concentrations of uric acid
can lead to
gout
and are associated with other medical conditions, including
diabetes
and the formation of ammonium acid urate
kidney stones
.
Chemistry
[
edit
]
Uric acid was first isolated from
kidney stones
in 1776 by Swedish chemist
Carl Wilhelm Scheele
.
[2]
In 1882, the Ukrainian chemist
Ivan Horbaczewski
first synthesized uric acid by melting
urea
with
glycine
.
[3]
Uric acid displays lactam?lactim
tautomerism
.
[4]
Uric acid crystallizes in the lactam form,
[5]
with
computational chemistry
also indicating that tautomer to be the most stable.
[6]
Uric acid is a
diprotic acid
with
p
K
a1
= 5.4 and p
K
a2
= 10.3.
[7]
At physiological pH, urate predominates in solution.
Lactam ion, a stable tautomer of uric acid
Urate ion, a tautomer of uric acid
Biochemistry
[
edit
]
The enzyme
xanthine oxidase
(XO)
catalyzes
the formation of uric acid from
xanthine
and
hypoxanthine
. XO, which is found in mammals, functions primarily as a dehydrogenase and rarely as an oxidase, despite its name.
[8]
) Xanthine in turn is produced from other
purines
. Xanthine oxidase is a large enzyme whose
active site
consists of the metal
molybdenum
bound to
sulfur
and oxygen.
[9]
Uric acid is released in
hypoxic
conditions (low oxygen saturation).
[10]
Water solubility
[
edit
]
In general, the water
solubility
of uric acid and its
alkali metal
and
alkaline earth
salts
is rather low. All these salts exhibit greater solubility in hot water than cold, allowing for easy recrystallization. This low solubility is significant for the
etiology
of gout. The solubility of the acid and its salts in
ethanol
is very low or negligible. In ethanol/water mixtures, the solubilities are somewhere between the end values for pure ethanol and pure water.
Solubility of urate salts (grams of water per gram of compound)
Compound
|
Cold water
|
Boiling water
|
Uric acid
|
15,000
|
2,000
|
Ammonium hydrogen urate
|
?
|
1,600
|
Lithium hydrogen urate
|
370
|
39
|
Sodium hydrogen urate
|
1,175
|
124
|
Potassium hydrogen urate
|
790
|
75
|
Magnesium dihydrogen diurate
|
3,750
|
160
|
Calcium dihydrogen diurate
|
603
|
276
|
Disodium urate
|
77
|
?
|
Dipotassium urate
|
44
|
35
|
Calcium urate
|
1,500
|
1,440
|
Strontium urate
|
4,300
|
1,790
|
Barium urate
|
7,900
|
2,700
|
The figures given indicate what mass of water is required to dissolve a unit mass of compound indicated. The lower the number, the more soluble the substance in the said solvent.
[11]
[12]
[13]
Genetic and physiological diversity
[
edit
]
Primates
[
edit
]
In
humans
uric acid (actually hydrogen urate ion) is the final
oxidation
(breakdown) product of
purine metabolism
and is excreted in urine, whereas in most other
mammals
, the enzyme
uricase
further oxidizes uric acid to
allantoin
.
[14]
The loss of uricase in higher primates parallels the similar loss of the ability to synthesize
ascorbic acid
, leading to the suggestion that urate may partially substitute for ascorbate in such species.
[15]
Both uric acid and ascorbic acid are strong
reducing agents
(
electron donors
) and potent
antioxidants
. In humans, over half the antioxidant capacity of
blood plasma
comes from hydrogen urate ion.
[16]
Humans
[
edit
]
The normal concentration range of uric acid (or hydrogen urate ion) in human blood is 25 to 80 mg/L for men and 15 to 60 mg/L for women
[17]
(but see below for slightly different values). An individual can have serum values as high as 96 mg/L and not have gout.
[18]
In humans, about 70% of daily uric acid disposal occurs via the kidneys, and in 5?25% of humans, impaired renal (kidney) excretion leads to
hyperuricemia
.
[19]
Normal excretion of uric acid in the urine is 270 to 360 mg per day (concentration of 270 to 360 mg/L if one litre of urine is produced per day ? higher than the solubility of uric acid because it is in the form of dissolved acid urates), roughly 1% as much as the daily excretion of
urea
.
[20]
Dogs
[
edit
]
The
Dalmatian
has a genetic defect in uric acid uptake by the
liver
and
kidneys
, resulting in decreased conversion to
allantoin
, so this breed excretes uric acid, and not allantoin, in the urine.
[21]
Birds, reptiles and desert-dwelling mammals
[
edit
]
In
birds
and
reptiles
, and in some desert-dwelling mammals (such as the
kangaroo rat
), uric acid also is the end product of purine metabolism, but it is excreted in
feces
as a dry mass. This involves a complex
metabolic pathway
that is energetically costly in comparison to processing of other nitrogenous wastes such as
urea
(from the
urea cycle
) or
ammonia
, but has the advantages of reducing water loss and preventing dehydration.
[22]
Invertebrates
[
edit
]
Platynereis dumerilii
, a marine
polychaete
worm, uses uric acid as a sexual
pheromone
. The female of the species releases uric acid into the water during
mating
, which induces males to release sperm.
[23]
Genetics
[
edit
]
Although foods such as meat and seafood can elevate serum urate levels, genetic variation is a much greater contributor to high serum urate.
[24]
[25]
A proportion of people have mutations in the urate transport proteins responsible for the excretion of uric acid by the kidneys. Variants of a number of genes, linked to serum urate, have so far been identified:
SLC2A9
;
ABCG2
;
SLC17A1
;
SLC22A11
;
SLC22A12
;
SLC16A9
;
GCKR
;
LRRC16A
; and
PDZK1
.
[26]
[27]
[28]
GLUT9, encoded by the
SLC2A9
gene, is known to transport both uric acid and
fructose
.
[19]
[29]
[30]
Myogenic
hyperuricemia
, as a result of the
purine nucleotide cycle
running when ATP reservoirs in muscle cells are low, is a common pathophysiologic feature of
glycogenoses
, such as
GSD-III
, which is a
metabolic myopathy
impairing the ability of ATP (energy) production for muscle cells.
[31]
In these metabolic myopathies, myogenic hyperuricemia is exercise-induced; inosine, hypoxanthine and uric acid increase in plasma after exercise and decrease over hours with rest.
[31]
Excess AMP (adenosine monophosphate) is converted into uric acid.
AMP → IMP → Inosine → Hypoxanthine → Xanthine → Uric Acid
Clinical significance and research
[
edit
]
In human
blood plasma
, the
reference range
of uric acid is typically 3.4?7.2 mg per 100 mL(200?430 μmol/L) for men, and 2.4?6.1 mg per 100 mL for women (140?360 μmol/L).
[32]
Uric acid concentrations in blood plasma above and below the normal range are known as, respectively,
hyperuricemia
and
hypouricemia
. Likewise, uric acid concentrations in urine above and below normal are known as
hyperuricosuria
and hypouricosuria. Uric acid levels in saliva may be associated with blood uric acid levels.
[33]
High uric acid
[
edit
]
Hyperuricemia
(high levels of uric acid), which induces
gout
, has various potential origins:
Gout
[
edit
]
A 2011 survey in the United States indicated that 3.9% of the population had gout, whereas 21.4% had hyperuricemia without having symptoms.
[41]
Excess blood uric acid (serum urate) can induce
gout
,
[42]
a painful condition resulting from needle-like crystals of uric acid termed
monosodium urate crystals
[43]
precipitating in
joints
,
capillaries
,
skin
, and other tissues.
[44]
Gout can occur where serum uric acid levels are as low as 6 mg per 100 mL (357 μmol/L), but an individual can have serum values as high as 9.6 mg per 100 mL (565 μmol/L) and not have gout.
[18]
In humans, purines are metabolized into uric acid, which is then excreted in the urine. Consumption of large amounts of some types of purine-rich foods, particularly meat and seafood, increases gout risk.
[45]
Purine-rich foods include liver, kidney, and sweetbreads, and certain types of seafood, including anchovies, herring, sardines, mussels, scallops, trout, haddock, mackerel, and tuna.
[46]
Moderate intake of purine-rich vegetables, however, is not associated with an increased risk of gout.
[45]
One treatment for gout in the 19th century was administration of
lithium
salts;
[47]
lithium urate is more soluble. Today, inflammation during attacks is more commonly treated with
NSAIDs
,
colchicine
, or
corticosteroids
, and urate levels are managed with
allopurinol
.
[48]
Allopurinol, which weakly inhibits xanthine oxidase, is an analog of hypoxanthine that is hydroxylated by
xanthine oxidoreductase
at the 2-position to give oxipurinol.
[49]
Tumor lysis syndrome
[
edit
]
Tumor lysis syndrome
, an emergency condition that may result from
blood cancers
, produces high uric acid levels in blood when tumor cells release their contents into the blood, either spontaneously or following
chemotherapy
.
[39]
Tumor lysis syndrome may lead to
acute kidney injury
when uric acid crystals are deposited in the kidneys.
[39]
Treatment includes
hyperhydration
to dilute and excrete uric acid via
urine
,
rasburicase
to reduce levels of poorly soluble uric acid in blood, or
allopurinol
to inhibit
purine
catabolism
from adding to uric acid levels.
[39]
Lesch?Nyhan syndrome
[
edit
]
Lesch?Nyhan syndrome
, a rare inherited disorder, is also associated with high serum uric acid levels.
[50]
Spasticity, involuntary movement, and cognitive retardation as well as manifestations of gout are seen in this syndrome.
[51]
Cardiovascular disease
[
edit
]
Hyperuricemia is associated with an increase in
risk factors
for
cardiovascular disease
.
[52]
It is also possible that high levels of uric acid may have a causal role in the development of atherosclerotic cardiovascular disease, but this is controversial and the data are conflicting.
[53]
Uric acid stone formation
[
edit
]
Comparison of different types of urinary crystals.
Kidney stones
can form through deposits of sodium urate microcrystals.
[54]
Saturation levels of uric acid in blood may result in one form of
kidney stones
when the urate crystallizes in the kidney. These uric acid stones are
radiolucent
, so do not appear on an abdominal plain
X-ray
.
[55]
Uric acid crystals can also promote the formation of
calcium oxalate
stones, acting as "seed crystals".
[56]
Diabetes
[
edit
]
Hyperuricemia is associated with components of
metabolic syndrome
, including in children.
[57]
[58]
Low uric acid
[
edit
]
Low uric acid (
hypouricemia
) can have numerous causes. Low dietary
zinc
intakes cause lower uric acid levels. This effect can be even more pronounced in women taking oral contraceptive medication.
[59]
Sevelamer
, a drug indicated for prevention of
hyperphosphataemia
in people with
chronic kidney failure
, can significantly reduce serum uric acid.
[60]
Multiple sclerosis
[
edit
]
Meta-analysis
of 10 case-control studies found that the serum uric acid levels of patients with
multiple sclerosis
were significantly lower compared to those of healthy controls, possibly indicating a diagnostic
biomarker
for multiple sclerosis.
[61]
Normalizing low uric acid
[
edit
]
Correcting low or deficient zinc levels can help elevate
serum
uric acid.
[62]
See also
[
edit
]
References
[
edit
]
- ^
https://pubchem.ncbi.nlm.nih.gov/compound/Uric-Acid
- ^
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.
2
: 73.
- ^
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.
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.
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.
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