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    Chemistry

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    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
    Urea API
    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

    Urea API

    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

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