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    Chemistry

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    Also known as: 97-59-6, 5-ureidohydantoin, Glyoxyldiureide, 1-(2,5-dioxoimidazolidin-4-yl)urea, Cordianine, Allantol
    Molecular Formula
    C4H6N4O3
    Molecular Weight
    158.12  g/mol
    InChI Key
    POJWUDADGALRAB-UHFFFAOYSA-N
    FDA UNII
    344S277G0Z
    Glyoxyldiureide
    A urea hydantoin that is found in URINE and PLANTS and is used in dermatological preparations.
    1 2D Structure

    Glyoxyldiureide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2,5-dioxoimidazolidin-4-yl)urea
    2.1.2 InChI
    InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
    2.1.3 InChI Key
    POJWUDADGALRAB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1(C(=O)NC(=O)N1)NC(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    344S277G0Z
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Herpecin L

    2. Herpecin-l

    3. Herpecinl

    4. Sebical

    5. Woun'dres

    2.3.2 Depositor-Supplied Synonyms

    1. 97-59-6

    2. 5-ureidohydantoin

    3. Glyoxyldiureide

    4. 1-(2,5-dioxoimidazolidin-4-yl)urea

    5. Cordianine

    6. Allantol

    7. Glyoxyldiureid

    8. Sebical

    9. Alantan

    10. Avc/dienestrolcream

    11. Urea, (2,5-dioxo-4-imidazolidinyl)-

    12. Hydantoin, 5-ureido-

    13. Psoralon

    14. Septalan

    15. Cutemol Emollient

    16. Uniderm A

    17. (2,5-dioxo-4-imidazolidinyl)urea

    18. Glyoxylic(acid) Diureide

    19. (2,5-dioxoimidazolidin-4-yl)urea

    20. Glyoxylic Diureide

    21. Nsc 7606

    22. Caswell No. 024

    23. Dl-allantoin

    24. 5-ureido-2,4-imidazolidindion

    25. N-(2,5-dioxo-4-imidazolidinyl)urea

    26. Alwextin

    27. Ccris 1958

    28. 2,5-dioxo-4-imidazolidinyl-urea

    29. Fancol Toin

    30. 5-ureidohydrantoin

    31. Epa Pesticide Chemical Code 085701

    32. (+/-)-allantoin

    33. 4-ureido-2,5-imidazolidinedione

    34. Ai3-15281

    35. Nsc7606

    36. Allantoin (jan/usp)

    37. Nsc-7606

    38. Idelalisib Metabolite M1a

    39. N-(2,5-dioxoimidazolidin-4-yl)urea

    40. 97-59-6 (racemic)

    41. Mls000737882

    42. 5377-33-3

    43. 5-ureido-2,4-imidazolidindione

    44. Chebi:15676

    45. 344s277g0z

    46. Urea, N-(2,5-dioxo-4-imidazolidinyl)-

    47. Dsstox_cid_43

    48. Herpecin L

    49. D00121

    50. Dsstox_rid_75334

    51. Dsstox_gsid_20043

    52. Allantoin [usan:ban]

    53. Smr000528073

    54. Sr-01000766252

    55. Einecs 202-592-8

    56. Mfcd00005260

    57. Brn 0102364

    58. Unii-344s277g0z

    59. Hsdb 7490

    60. Allantoin [usan:usp:ban:jan]

    61. Cas-97-59-6

    62. Prestwick_11

    63. Ncgc00016358-01

    64. Allation,(s)

    65. 5-ureido-hydantoin

    66. Allantoin (8ci)

    67. Spectrum_001078

    68. Allantoin [jan]

    69. Allantoin [ii]

    70. Allantoin [mi]

    71. Allantoin [hsdb]

    72. Allantoin [inci]

    73. Allantoin [usan]

    74. Prestwick0_000002

    75. Prestwick1_000002

    76. Prestwick2_000002

    77. Prestwick3_000002

    78. Spectrum2_000219

    79. Spectrum3_000876

    80. Spectrum4_000716

    81. Spectrum5_001526

    82. Allantoin [vandf]

    83. Allantoin [mart.]

    84. Bmse000437

    85. Ec 202-592-8

    86. Allantoin [usp-rs]

    87. Allantoin [who-dd]

    88. Schembl3208

    89. Oprea1_621175

    90. Bspbio_000003

    91. Bspbio_002551

    92. Kbiogr_001271

    93. Kbioss_001558

    94. 5-25-15-00338 (beilstein Handbook Reference)

    95. Mls002473300

    96. Allantoin, Analytical Standard

    97. Divk1c_000281

    98. Spectrum1500801

    99. Allantoin-[13c2,15n4]

    100. Spbio_000237

    101. Spbio_001924

    102. Bpbio1_000005

    103. Chembl593429

    104. Allantoin [ep Monograph]

    105. Dtxsid3020043

    106. Sd 101 [who-dd]

    107. 5-ureidohydantoin;glyoxyldiureide

    108. Hms500o03

    109. Kbio1_000281

    110. Kbio2_001558

    111. Kbio2_004126

    112. Kbio2_006694

    113. Kbio3_002051

    114. Sd 101

    115. Allantoin [usp Monograph]

    116. Allantoin, >=98.0% (n)

    117. Ninds_000281

    118. Urea,5-dioxo-4-imidazolidinyl)-

    119. Hms1568a05

    120. Hms1921i10

    121. Hms2092k16

    122. Hms2095a05

    123. Hms2268n08

    124. Hms3712a05

    125. Hms3885m08

    126. Pharmakon1600-01500801

    127. Amy13912

    128. Bcp31832

    129. Component Of Skin-balm (salt/mix)

    130. Hy-n0543

    131. 2,5-imidazolidinedione, 4-ureido-

    132. Tox21_110395

    133. Tox21_202087

    134. Tox21_302912

    135. Bbl027508

    136. Ccg-39781

    137. Nsc757792

    138. S3856

    139. Stl373778

    140. Akos000120642

    141. Akos016038547

    142. Tox21_110395_1

    143. Cs-7741

    144. Db11100

    145. Nsc-757792

    146. Sdccgmls-0066595.p001

    147. 1-(2,5-dioxoimidazolidin-4-yl);urea

    148. Idi1_000281

    149. Allantoin, P.a., 98.5-101.0%

    150. N-(2,5-dioxo-4-imidazolidinyl)urea #

    151. Ncgc00094854-01

    152. Ncgc00094854-02

    153. Ncgc00094854-03

    154. Ncgc00094854-04

    155. Ncgc00094854-05

    156. Ncgc00094854-06

    157. Ncgc00094854-07

    158. Ncgc00256403-01

    159. Ncgc00259636-01

    160. Ac-11040

    161. As-13865

    162. Nci60_041675

    163. Sodium Methanethiolate (~20% In Water)

    164. N-(2,5-dioxo-4(1h)-imidazolidinyl)urea

    165. Sbi-0051759.p002

    166. A0211

    167. Ab00052307

    168. Ft-0604592

    169. C01551

    170. D85069

    171. Urea, (2,5-dioxo-4-imidazolidinyl)- (9ci)

    172. Ab00052307_11

    173. 3-hydroxy-2-propyl-4-pentenoic Acid Ethyl Ester

    174. Q409804

    175. J-522839

    176. Sr-01000766252-2

    177. Sr-01000766252-3

    178. Sr-01000766252-4

    179. W-100104

    180. Allantoin, European Pharmacopoeia (ep) Reference Standard

    181. A999f0d6-0285-41d9-a6ba-b705987b663c

    182. Allantoin, United States Pharmacopeia (usp) Reference Standard

    183. Allantoin, Pharmaceutical Secondary Standard; Certified Reference Material

    184. 5-ureidohydantoin; Glyoxyldiureide; Glyoxylic Diureide; Cordianine; Glyoxyldiureid; (2,5-dioxo-4-imidazolidinyl)urea

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 158.12 g/mol
    Molecular Formula C4H6N4O3
    XLogP3-2.2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass158.04399007 g/mol
    Monoisotopic Mass158.04399007 g/mol
    Topological Polar Surface Area113 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity225
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    A urea hydantoin that is found in URINE and PLANTS and is used in dermatological preparations.

    National Library of Medicine, SIS; ChemIDplus Record for Allantoin ( 97-59-6), MESH Heading. Available from, as of February 1, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp

    Allantoin, a component in Comfrey, stimulates tissue repair and wound healing through cell proliferation. Allantoin has also had significant effect on cellular multiplication in degenerating and regenerating peripheral nerves.

    PDR for Herbal Medicines; Medical Economics Co., Montvale, NJ. p. 212 (2000)

    In humans, the allantoin to uric acid ratio in plasma increases during oxidative stress, thus this ratio has been suggested to be an in vivo marker for oxidative stress in humans.

    PMID:16705445 Tsahar E et al; J Comp Physiol (B) 176 (7): 653-61 (2006)

    Diagnostic marker for oxidative stress during antituberculous (anti-TB) therapy.

    PMID:7546339 Walubo A et al; Biomed Environ Sci 8 (2): 106-13 (1995)

    For more Therapeutic Uses (Complete) data for ALLANTOIN (8 total), please visit the HSDB record page.

    4.2 Drug Warning

    Skin: For external use only. Ocular: Avoid contact with eyes. Sensitization: Mederma is contraindicated in individuals who have shown hypersensitivity to any of its components /Mederma/

    Merz Pharmaceuticals, LLC; Material Safety Data Sheet, Mederma. December 12, 2002

    4.3 Drug Indication

    Allantoin is commonly applied in a variety of topical vehicles or applications such as cosmetic creams, toothpastes, mouthwashes, shampoos, lipsticks, anti-acne products, and lotions for the purpose of moisturizing skin, enhancing the smoothness of skin, stimulating the healing of wounds, and soothing irritated skin.

    FDA Label

    Treatment of epidermolysis bullosa

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    There is no well controlled and appropriate data that can formally substantiate the pharmacodynamic properties of allantoin. Nevertheless, ongoing studies suggest that allantoin possesses moisturizing and keratolytic effects, as well as abilities to increase the water content of the extracellular matrix and enhance the desquamation of upper layers of dead skin cells, all of which are activities that can promote cell proliferation and facilitate wound healing.

    5.2 MeSH Pharmacological Classification

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    In studies on human subjects, a recovery of 19% and 34% of allantoin in the urine was observed but only in two individuals and only after the administration of massive doses of allantoin. After intravenous administration, recovery in the urine was practically quantitative with doses of 75 to 600 mgm in the human model. After 240 mgm, excretion continued for 72 hours in human subjects and the results were similar in regards to subcutaneous injection.

    Route of Elimination

    Urinary clearance is the predominant excretion route.

    Clearance

    Some studies suggest that the average renal clearance of allantoin in normal, healthy human subjects is approximately 123 cc per minute. It is generally agreed upon that exogenously administered allantoin is rapidly excreted.

    Allantoin administered to dogs orally as solid or solution was excreted in the urine to an extent of between 35 and 92 per cent within 24 hours. No allantoin was recovered either in urine or feces when given to rabbits orally. In man the recovery was 19 and 34 per cent in two individuals after massive doses. After intravenous administration recovery in the urine was practically quantitative with doses of 75 to 600 mgm. in the dog and in man. After 240 mgm. in man excretion continued for 72 hours. The results were similar after subcutaneous injection. Uric acid injected intravenously into a dog was converted into allantoin within two hours.

    Young EG et al; J Pharmacol Exptl Ther 81 (1): 1-9 (1944)

    5.4 Metabolism/Metabolites

    Uricase is the enzyme that possesses the functionality to convert uric acid to allantoin. Considering humans do not possess any endogenous uricase, uric acid is the only final breakdown product in the purine degradation of unwanted waste product purine nucleotides. The presence of allantoin in human urine is subsequently the result of non-enzymatic processes on uric acid with reactive oxygen species. Such non-enzymatic processes are consequently potentially suitable biomarkers for measuring oxidative stress in chronic illnesses and aging. Furthermore, as allantoin is found endogenously and is part of basic, natural metabolic pathways, no accumulation is expected of it. Additionally, allantoin is not believed to be metabolized to a measurable extent in humans and animals.

    In humans, uric acid is the final breakdown product of unwanted purine nucleotides. Uric acid is the last stage in purine degradation, because humans lack the enzyme uricase which converts uric acid into allantoin.

    PMID:15493112 Hediger MA; Ther Umsch 61 (9): 541-5 (2004)

    Allantoin in the presence of calcium ions has been implicated as a potential toxic agent in Reye's syndrome. An investigation of possible alternative sources of allantoin in humans, which lack the enzyme uricase, has been initiated. Urate is a strong reducing agent which can reduce cytochrome c nonenzymatically, with the concomitant production of CO2 and H+. The stoichiometries measured for the various reactants and products were 1 urate:2 cytochrome c:1 H+:1 CO2. The initial reaction rate depended on the concentrations of both urate and cytochrome c, with reaction kinetics that were first order with respect to urate and second order with respect to cytochrome c. The participation of molecular oxygen in this reaction could not be detected. The pH and ionic strength optima for this reaction were determined to be 9.5-10.5 and 10(-5) M, respectively. Based on the results reported here, the following balanced equation can be written: urate-2 + 2 cytochrome c+3 + 2 H2O----allantoin + 2 cytochrome c+2 + H+ + HCO3-. /The authors/ propose that allantoin can be generated from the oxidation of urate by cytochrome c+3, and that this is a potential source of allantoin in human tissues.

    PMID:3028263 Martens ME et al; Arch Biochem Biophys 252 (1):91-6 (1987)

    Uric acid is the main nitrogenous waste product in birds but it is also known to be a potent antioxidant. Hominoid primates and birds lack the enzyme urate oxidase, which oxidizes uric acid to allantoin. Consequently, the presence of allantoin in their plasma results from non-enzymatic oxidation.

    PMID:16705445 Tsahar E et al; J Comp Physiol (B) 176 (7): 653-61 (2006)

    In most mammals purine degradation ultimately leads to the formation of allantoin. Humans lack the enzyme uricase, which catalyzes the conversion of uric acid to allantoin.

    PMID:16375732 Masseoud D et al; Curr Pharm Des 11 (32): 4117-24 (2005)

    For more Metabolism/Metabolites (Complete) data for ALLANTOIN (11 total), please visit the HSDB record page.

    5.5 Biological Half-Life

    When studied in cattle, sheep, and horses, the half-life of allantoin is in the range of 1 to 2.5 hours.

    5.6 Mechanism of Action

    There is no well controlled data that can formally substantiate the method of action. However, ongoing studies suggest that there may exist a histological wound healing profile induced by allantoin in rats that leads to the amelioration and fastening of the reestablishment of normal skin. This facilitation of wound healing is supported by observations that wounds inflicted to rat subjects to which topical allantoin preparations were applied histologically demonstrated increased vasodilation, presence of inflammatory exudates, number of inflammatory cells, angiogenesis, fibroblast proliferation, and increased collagen deposition when compared to rat subjects with wounds that did not receive any allantoin administration.

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