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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

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 Formula	C₄H₆N₄O₃
Molecular Weight	158.12 g/mol
XLogP3	-2.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	158.04399007 g/mol
Monoisotopic Mass	158.04399007 g/mol
Topological Polar Surface Area	113 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	225
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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