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2D Structure
Also known as: Carbamide, 57-13-6, Carbonyldiamide, Isourea, Ureophil, Carbonyldiamine
Molecular Formula
CH4N2O
Molecular Weight
60.056  g/mol
InChI Key
XSQUKJJJFZCRTK-UHFFFAOYSA-N
FDA UNII
8W8T17847W

A compound formed in the liver from ammonia produced by the deamination of amino acids. It is the principal end product of protein catabolism and constitutes about one half of the total urinary solids.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
urea
2.1.2 InChI
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
2.1.3 InChI Key
XSQUKJJJFZCRTK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(=O)(N)N
2.2 Other Identifiers
2.2.1 UNII
8W8T17847W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Basodexan

2. Carbamide

3. Carmol

2.3.2 Depositor-Supplied Synonyms

1. Carbamide

2. 57-13-6

3. Carbonyldiamide

4. Isourea

5. Ureophil

6. Carbonyldiamine

7. Ureaphil

8. Carbamimidic Acid

9. Pseudourea

10. Urevert

11. Alphadrate

12. Aquadrate

13. Calmurid

14. Carbaderm

15. Keratinamin

16. Carbonyl Diamide

17. Pastaron

18. Urepearl

19. Carbamide Resin

20. Ultra Mide

21. Varioform Ii

22. Aqua Care

23. Prespersion, 75 Urea

24. B-i-k

25. Basodexan

26. Carmol

27. Harnstoff

28. Mocovina

29. Nutraplus

30. Supercel 3000

31. Aqua Care Hp

32. Ureacin-20

33. Ureacin-10 Lotion

34. Ureacin-40 Creme

35. Onychomal

36. Panafil

37. Polyurea

38. Hyanit

39. Caswell No. 902

40. Carbonyl Diamine

41. Nci-c02119

42. Ccris 989

43. Aminoketone

44. Aquacare

45. Hsdb 163

46. Carbamimic Acid

47. Bubber Shet

48. Elaqua Xx

49. Keratinamin Kowa

50. Nsc 34375

51. Benural 70

52. Urea Ammonium Nitrate Solution

53. Epa Pesticide Chemical Code 085702

54. Ur

55. Ai3-01202

56. Carbamide;carbonyldiamide

57. Mfcd00008022

58. Nsc-34375

59. Azodicarboxylic Acid-diamide

60. Ins No.927a

61. E927b

62. (nh2)2co

63. Ins-927a

64. 37955-36-5

65. Helicosol

66. Chebi:16199

67. Urea Solution

68. E-927a

69. 8w8t17847w

70. 4744-36-9

71. Ncgc00090892-01

72. Dsstox_cid_1426

73. Dsstox_rid_76155

74. Mocovina [czech]

75. Dsstox_gsid_21426

76. Ure

77. Harnstoff [german]

78. Urea [jan]

79. Ureum

80. Antisepsis Bolus

81. Sterile Urea

82. Cas-57-13-6

83. Urea [usp:jan]

84. Urea, Acs

85. Einecs 200-315-5

86. Uree

87. Isoharnstoff

88. Cerovel

89. Karbamid

90. Urepeal

91. Uroderm

92. Amino Ketone

93. Amino-ketone

94. Urea Perhydrate

95. Pastaron Soft

96. Urea, Ultrapure

97. E-cardamoni

98. Aquacare Hp

99. Unii-8w8t17847w

100. Urepeal L

101. Carbamide Solution

102. Urea, Homopolymer

103. Beta-i-k

104. Pastaron 10

105. Pastaron 20

106. Pastaron (tn)

107. Pastaron 20 Soft

108. Carbonamidimidic Acid

109. Carmol 40

110. Cerovel (salt/mix)

111. Panafil (salt/mix)

112. Rubinol St 010

113. Urea, P.a.

114. Optigen 1200

115. Urea, 2m

116. Urea,(s)

117. Spectrum_000672

118. Urea [vandf]

119. Wln: Zvz

120. Carbamimidic Acid (van)

121. Spectrum2_001192

122. Spectrum3_001791

123. Spectrum4_001168

124. Spectrum5_001862

125. Urea (jp17/usp)

126. Urea, Analytical Standard

127. Urea, For Electrophoresis

128. Urea [hpus]

129. Urea [hsdb]

130. Urea [inci]

131. Urea (8ci,9ci)

132. Urea [fcc]

133. Urea [usp-rs]

134. Urea [who-dd]

135. Eucerin 10% Urea Lotion

136. Chembl985

137. Urea [ii]

138. Urea [mart.]

139. Urea [mi]

140. Ec 200-315-5

141. Urea [orange Book]

142. H2n-co-nh2

143. H2nc(o)nh2

144. Urea [ep Monograph]

145. Urea [usp Impurity]

146. Urea A.c.s. Reagent Grade

147. H2n-c(oh)=nh

148. Bspbio_003341

149. Kbiogr_001775

150. Kbioss_001152

151. U-cort Component Urea

152. Urea [usp Monograph]

153. Urea, Puriss., 99.5%

154. Mls001076688

155. Divk1c_000086

156. H2n-c(=nh)-oh

157. Ho-c(=nh)-nh2

158. Spectrum1500604

159. Urea, Ar, >=99%

160. Urea, Lr, >=99%

161. Spbio_001263

162. Alphaderm Component Urea

163. Gtpl4539

164. Carmol Hc Component Urea

165. Dtxsid4021426

166. Urea Component Of U-cort

167. Urea, >=99.0%

168. Urea, Molecular Biology Reagent

169. Bdbm24961

170. Chebi:48376

171. Hms500e08

172. Kbio1_000086

173. Kbio2_001152

174. Kbio2_003720

175. Kbio2_006288

176. Kbio3_002843

177. Calmurid Hc Component Urea

178. Urea 100 Microg/ml In Methanol

179. Ninds_000086

180. Hms1921i17

181. Hms2092c08

182. Hms2232p21

183. Pharmakon1600-01500604

184. Urea Component Of Alphaderm

185. Component Of Artra Ashy Skin Cream

186. Urea Component Of Carmol Hc

187. Amy37159

188. Bcp30439

189. Cs-b1800

190. Hy-y0271

191. Nsc34375

192. Str00449

193. Urea, Tested According To Ph.eur.

194. Zinc8214514

195. Tox21_111036

196. Tox21_202158

197. Tox21_300035

198. C0165

199. Ccg-40265

200. Nsc757375

201. S3687

202. Stl194286

203. Urea Component Of Calmurid Hc

204. Urea, Reagentplus(r), >=99.5%

205. Akos009031424

206. Urea, Nist(r) Srm(r) 2141

207. Urea, Saj First Grade, >=98.0%

208. Db03904

209. Nsc-757375

210. Urea, Jis Special Grade, >=99.0%

211. Urea, Meets Usp Testing Specifications

212. Urea, Vetec(tm) Reagent Grade, 99%

213. Idi1_000086

214. Urea Solution, 40 % (w/v) In H2o

215. Basodexan Pound>>carmol Pound>>carbamide

216. Ncgc00090892-02

217. Ncgc00090892-03

218. Ncgc00090892-04

219. Ncgc00090892-05

220. Ncgc00090892-06

221. Ncgc00254181-01

222. Ncgc00259707-01

223. Urea Solution, Bioultra, ~8 M In H2o

224. Smr000499585

225. Urea, Acs Reagent, 99.0-100.5%

226. 4,4-(3-oxapentanediyldioxy)dibenzaldehyde

227. Allantoin Impurity B [ep Impurity]

228. Sbi-0051552.p002

229. Urea, Bioreagent, Suitable For Cell Culture

230. B7781

231. Fluorouracil Impurity G [ep Impurity]

232. Ft-0645129

233. Ft-0675737

234. Ft-0675738

235. U0073

236. U0077

237. Urea, Reagentplus(r), >=99.5%, Pellets

238. Urea Solution, For Microbiology, 40% In H2o

239. C00086

240. Component Of Artra Ashy Skin Cream (salt/mix)

241. D00023

242. D70446

243. M02656

244. Q48318

245. Urea, P.a., Acs Reagent, 99.0-100.5%

246. Ab00052123_05

247. Sr-01000762961

248. Urea, Nist(r) Srm(r) 912a, Clinical Standard

249. Sr-01000762961-2

250. Urea, British Pharmacopoeia (bp) Reference Standard

251. Urea, European Pharmacopoeia (ep) Reference Standard

252. F0001-1490

253. Urea, Bioultra, For Molecular Biology, >=99.5% (t)

254. Urea, Bioxtra, Ph 7.5-9.5 (20 C, 5 M In H2o)

255. Urea, Nist Srm 2152, Combustion Calorimetric Standard

256. Z230747540

257. Urea, United States Pharmacopeia (usp) Reference Standard

258. 6e4eb293-4363-4d38-bf3b-1397372c31e5

259. Urea, 8 M (after Reconstitution With 16 Ml High Purity Water)

260. Urea, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99.5%

261. Urea, Pharmaceutical Secondary Standard; Certified Reference Material

262. Urea, Powder, Bioreagent, For Molecular Biology, Suitable For Cell Culture

263. Urea, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Usp, 99.0-100.5%, 99.0-101.0% (calc. On Dry Substance)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 60.056 g/mol
Molecular Formula CH4N2O
XLogP3-1.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass60.032362755 g/mol
Monoisotopic Mass60.032362755 g/mol
Topological Polar Surface Area69.1 Ų
Heavy Atom Count4
Formal Charge0
Complexity29
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Dermatologic Agents; Diuretics, Osmotic

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


UREA IS /USED LESS COMMONLY THAN OTHER OSMOTIC AGENTS/ FOR THE SHORT-TERM REDUCTION OF INTRAOCULAR PRESSURE & VITREOUS VOL ... IN ANGLE-CLOSURE GLAUCOMA .. PRIOR TO SURGERY ... IN CHRONIC GLAUCOMA ... PRE- AND POSTOPERATIVE TREATMENT.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1825


DOSE--USUAL, IV INFUSION, 100 MG TO 1 G/KG DAILY, AS 30% SOLN IN DEXTROSE INJECTION @ RATE NOT EXCEEDING 4 ML/MIN.

GENNARO. REMINGTON'S PHARM SCI 17TH ED 1985 p 935


USED TOPICALLY IN THE TREATMENT OF PSORIASIS, ICHTHYOSIS, ATOPIC DERMATITIS, AND OTHER DRY, SCALY CONDITIONS.

GENNARO. REMINGTON'S PHARM SCI 17TH ED 1985 p 785


For more Therapeutic Uses (Complete) data for UREA (14 total), please visit the HSDB record page.


4.2 Drug Warning

UREA SHOULD NOT BE USED IN PATIENTS WITH SEVERELY IMPAIRED RENAL FUNCTION.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 936


UREA IS OFTEN RECONSTITUTED WITH INVERT SUGAR SOLN. INVERT SUGAR CONTAINS FRUCTOSE, WHICH CAN CAUSE SEVERE REACTION (HYPOGLYCEMIA, NAUSEA, VOMITING, TREMORS, COMA, & CONVULSIONS) IN PATIENTS WITH HEREDITARY FRUCTOSE INTOLERANCE (ALDOLASE DEFICIENCY).

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 936


In general osmotic diuretics are contraindicated in patients who are anuric due to severe renal disease or who are unresponsive to test doses of the drugs. Urea may cause thrombosis or pain if extravasation occurs, and it should not be admin to patients with impaired liver function because of the risk of elevation of blood ammonia levels. Both mannitol and urea are contraindicated in patients with active cranial bleeding.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 696


4.3 Minimum/Potential Fatal Human Dose

In ruminants unaccustomed to urea, ingestion of 0.3-0.5 g urea/kg may be toxic ... The toxic dose of urea in (presumably unaccustomed) cattle is 0.45 g/kg (50 g total dose) but that animals can ingest more urea than this if the dose is increased gradually.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 1029


4.4 Drug Indication

  • 10% hydrate skin
  • 15% accelerate fibrin degradation
  • 20-30% are antipruritic, break down keratin, decrease the thickness of the stratum corneum and are used in scaling conditions such as ichthysosis
  • 40% are proteolytic and may be used to dissolve and peel dystrophic nails

[Patient Self Care, 2010]


5 Pharmacology and Biochemistry
5.1 Pharmacology

As a humectant, urea draws water into the striatum corneum.


5.2 ATC Code

B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05B - I.v. solutions

B05BC - Solutions producing osmotic diuresis

B05BC02 - Carbamide


D - Dermatologicals

D02 - Emollients and protectives

D02A - Emollients and protectives

D02AE - Carbamide products

D02AE01 - Carbamide


5.3 Absorption, Distribution and Excretion

SOME SMALL, WATER SOL, BUT NONIONIZABLE COMPD SUCH AS UREA READILY TRAVERSE MAMMALIAN MEMBRANES, PROBABLY ALONG WITH WATER, BY WAY OF THE PORES. THIS FILTRATION PROCESS IS PARTICULARLY RAPID BETWEEN CAPILLARIES & EXTRACELLULAR FLUID.

Hayes, W.J., Jr., E.R. Laws Jr., (eds.). Handbook of Pesticide Toxicology Volume 1. General Principles. New York, NY: Academic Press, Inc., 1991., p. 127


... UREA ... PENETRATES OTHER CELLS RAPIDLY, ENTERS THE BRAIN ONLY VERY SLOWLY ...

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 51


... DISTRIBUTED APPROX IN TOTAL BODY WATER ... HAVE BEEN USED FOR MEASUREMENT OF TOTAL BODY WATER.

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 53


EXCRETION OF UREA DURING SWEATING IN MAN: 1.84 SWEAT/PLASMA RATIO WITH PKA @ 13.8. /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 143


For more Absorption, Distribution and Excretion (Complete) data for UREA (6 total), please visit the HSDB record page.


5.4 Mechanism of Action

... The primary mechanism of ammonia toxicosis appears to be inhibition of the citric acid cycle. There is an increase in anaerobic glycolysis, blood glucose, and blood lactate ... . Acidosis is manifested. The exact means by which ammonia blocks the citric acid cycle is not known. It is postulated that ammonia saturation of the glutamine-synthesizing system causes a backing-up in the citrate cycle, a decrease in its intermediates, and a decrease in energy production and cellular respiration, which leads to convulsions ... . The decrease of citrate cycle intermediates is postulated to result from reamination of pyruvic, ketoglutaric, and oxaloacetic acids.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 1031