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Identification
NameUrea
Accession NumberDB03904  (EXPT03203)
Typesmall molecule
Groupsexperimental
Description

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. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number57-13-6
WeightAverage: 60.0553
Monoisotopic: 60.03236276
Chemical FormulaCH4N2O
InChI KeyInChIKey=XSQUKJJJFZCRTK-UHFFFAOYSA-N
InChI
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
IUPAC Name
urea
SMILES
NC(N)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsNot Available
SubstituentsNot Available
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
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]
PharmacodynamicsAs a humectant, urea draws water into the striatum corneum.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Ethacrynic Acid Action PathwayDrug actionSMP00097
Argininosuccinic AciduriaDiseaseSMP00003
Chlorothiazide Action PathwayDrug actionSMP00078
Polythiazide Action PathwayDrug actionSMP00080
Methyclothiazide Action PathwayDrug actionSMP00081
Bumetanide Action PathwayDrug actionSMP00088
Bendroflumethiazide Action PathwayDrug actionSMP00090
Quinethazone Action PathwayDrug actionSMP00091
Hydrochlorothiazide Action PathwayDrug actionSMP00100
Cyclothiazide Action PathwayDrug actionSMP00103
Metolazone Action PathwayDrug actionSMP00105
Hydroflumethiazide Action PathwayDrug actionSMP00108
Indapamide Action PathwayDrug actionSMP00110
Furosemide Action PathwayDrug actionSMP00115
Torsemide Action PathwayDrug actionSMP00118
Trichlormethiazide Action PathwayDrug actionSMP00121
Chlorthalidone Action PathwayDrug actionSMP00122
Triamterene Action PathwayDrug actionSMP00132
Amiloride Action PathwayDrug actionSMP00133
Spironolactone Action PathwayDrug actionSMP00134
Eplerenone Action PathwayDrug actionSMP00135
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)DiseaseSMP00362
L-arginine:glycine amidinotransferase deficiencyDiseaseSMP00507
Ornithine Aminotransferase Deficiency (OAT Deficiency)DiseaseSMP00363
Arginine and Proline MetabolismMetabolicSMP00020
D-Arginine and D-Ornithine MetabolismMetabolicSMP00036
ArgininemiaDiseaseSMP00357
Hyperornithinemia with gyrate atrophy (HOGA)DiseaseSMP00505
Blue diaper syndromeDiseaseSMP00583
Carbamoyl Phosphate Synthetase DeficiencyDiseaseSMP00002
Citrullinemia Type IDiseaseSMP00001
Creatine deficiency, guanidinoacetate methyltransferase deficiencyDiseaseSMP00504
Urea CycleMetabolicSMP00059
Glucose Transporter Defect (SGLT2)DiseaseSMP00245
Prolidase Deficiency (PD)DiseaseSMP00207
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)DiseaseSMP00188
Ornithine Transcarbamylase Deficiency (OTC Deficiency)DiseaseSMP00205
Hartnup DisorderDiseaseSMP00189
Kidney FunctionPhysiologicalSMP00483
Renal GlucosuriaDiseaseSMP00184
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]DiseaseSMP00506
Hyperprolinemia Type IIDiseaseSMP00360
Hyperprolinemia Type IDiseaseSMP00361
Prolinemia Type IIDiseaseSMP00208
IminoglycinuriaDiseaseSMP00193
IminoglycinuriaDiseaseSMP00584
Lysinuric Protein IntoleranceDiseaseSMP00197
Lysinuric protein intolerance (LPI)DiseaseSMP00585
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9513
Blood Brain Barrier + 0.981
Caco-2 permeable - 0.8956
P-glycoprotein substrate Non-substrate 0.8517
P-glycoprotein inhibitor I Non-inhibitor 0.982
P-glycoprotein inhibitor II Non-inhibitor 0.9875
Renal organic cation transporter Non-inhibitor 0.9343
CYP450 2C9 substrate Non-substrate 0.7982
CYP450 2D6 substrate Non-substrate 0.793
CYP450 3A4 substrate Non-substrate 0.8449
CYP450 1A2 substrate Non-inhibitor 0.9661
CYP450 2C9 substrate Non-inhibitor 0.8771
CYP450 2D6 substrate Non-inhibitor 0.9878
CYP450 2C19 substrate Non-inhibitor 0.974
CYP450 3A4 substrate Non-inhibitor 0.9724
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9695
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.6955
Biodegradation Ready biodegradable 0.5354
Rat acute toxicity 0.8822 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.981
hERG inhibition (predictor II) Non-inhibitor 0.9824
Pharmacoeconomics
Manufacturers
  • Hospira inc
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point132.7 °CPhysProp
water solubility5.45E+005 mg/L (at 25 °C)YALKOWSKY,SH (1989)
logP-2.11HANSCH,C ET AL. (1995)
logS0.96ADME Research, USCD
Caco2 permeability-5.34ADME Research, USCD
pKa0.1 (at 21 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
water solubility4.12e+02 g/lALOGPS
logP-1.8ALOGPS
logP-1.4ChemAxon
logS0.84ALOGPS
pKa (strongest acidic)15.73ChemAxon
pKa (strongest basic)-2.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count2ChemAxon
polar surface area69.11ChemAxon
rotatable bond count0ChemAxon
refractivity13.14ChemAxon
polarizability5.1ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Ryo Yoshida, Haruhiko Katoh, Seizo Sumida, Ichiki Takemoto, Junya Takahashi, Katsuzo Kamoshita, “Urea derivatives, and their production and use.” U.S. Patent US4334912, issued 0000.

US4334912
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00023
KEGG CompoundC00086
PubChem Compound1176
PubChem Substance46508687
BindingDB24961
ChEBI16199
ChEMBL
PharmGKBPA451831
HETURE
Drugs.comhttp://www.drugs.com/cons/urea-intravenous.html
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food InteractionsNot Available

1. Arginase-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Arginase-1 P05089 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Carbonic anhydrase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Carbonic anhydrase 2 P00918 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Structural polyprotein

Kind: protein

Organism: VEEV

Pharmacological action: unknown

Components

Name UniProt ID Details
Structural polyprotein P09592 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Catenin beta-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Catenin beta-1 P35222 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Sulfoxide reductase catalytic subunit YedY

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: unknown

Components

Name UniProt ID Details
Sulfoxide reductase catalytic subunit YedY Q8XB74 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Dihydrofolate reductase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydrofolate reductase P0ABQ4 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

1. Urea transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Urea transporter 2 Q15849 Details

References:

  1. Wall SM, Han JS, Chou CL, Knepper MA: Kinetics of urea and water permeability activation by vasopressin in rat terminal IMCD. Am J Physiol. 1992 Jun;262(6 Pt 2):F989-98. Pubmed

2. Urea transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Urea transporter 1 Q13336 Details

References:

  1. Ripoche P, Rousselet G: [Urea transporters]. Nephrologie. 1996;17(7):383-8. Pubmed
  2. Olives B, Mattei MG, Huet M, Neau P, Martial S, Cartron JP, Bailly P: Kidd blood group and urea transport function of human erythrocytes are carried by the same protein. J Biol Chem. 1995 Jun 30;270(26):15607-10. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23