Identification

Name
Urea
Accession Number
DB03904  (EXPT03203)
Type
Small Molecule
Groups
Approved
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
Synonyms
Not Available
External IDs
E-927A / INS NO.927A / INS-927A / NSC-34375
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Calmurid CrmCream100 mgTopicalGalderma1994-12-311999-07-27Canada
Carbamex 330mgmsTablet330 mgOralTherapeutic Foods Co.1989-12-152009-07-24Canada
Urederm Cream 10%Cream10 %TopicalChartwell Industries (Canada) Ltd.1995-12-312009-06-19Canada
Uremol 10 Crm 10%Cream10 %TopicalTrans Canaderm Inc.1987-12-312000-10-27Canada
Uremol 10 Lotion 10%Lotion10 %TopicalTrans Canaderm Inc.1979-12-312000-10-27Canada
Velvelan Crm 10%Cream10 %TopicalMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1978-12-311997-08-14Canada
Velvelan Lot 10%Lotion10 %TopicalMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1978-12-311997-08-14Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AluveaCream39 g/100gTopicalMerz Pharmaceuticals2011-04-15Not applicableUs
Carb-O-PhilicCream20 g/100gTopicalGeritrex Llc2015-01-212016-01-05Us
Carb-O-PhilicCream10 g/100gTopicalGeritrex Llc2015-01-202016-01-05Us
CEM-UreaSolution.45 mL/mLTopicalPru Gen Pharmaceuticals2011-07-01Not applicableUs
Gehwol FUSSKRAFT Callus SoftenerLiquid250 mg/mLTopicalEduard Gerlach Gmb H2008-03-242017-04-14Us
Gehwol med CallusCream180 mg/mLTopicalEduard Gerlach Gmb H2010-07-082017-04-14Us
Gehwol med LipidroCream100 mg/mLTopicalEduard Gerlach Gmb H2005-06-252017-04-14Us
Gordons Urea 40Ointment.4 g/gTopicalGordon Laboratories2010-07-16Not applicableUs
Hydro 35Aerosol, foam35 g/100gTopicalExeltis Usa Dermatology, Llc2009-06-20Not applicableUs
KeralacCream470 mg/gTopicalBrava2011-07-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Calmurid HC CrmUrea (100 mg) + Hydrocortisone (10 mg)CreamTopicalGalderma1994-12-312000-08-02Canada
Dr. Scholl's Cracked Heel Relief CreamUrea (5 %) + Benzalkonium chloride (0.13 %) + Lidocaine (2 %)CreamTopicalSchering Plough2003-03-292012-07-24Canada
Flexitol Heel BalmUrea (25.0 %) + Lanolin (9.88 %) + Petrolatum (9.88 %)CreamTopicalLaderma Trading Pty Ltd.2006-08-212012-06-27Canada
Heel BalmUrea (10.0 %) + Lanolin (9.88 %) + Petrolatum (9.88 %)CreamTopicalTanta Pharmaceuticals IncNot applicableNot applicableCanada
Hydrophil OntUrea (5 %) + Mineral oil (64.5 %)OintmentTopicalOmega Laboratories Ltd1983-12-31Not applicableCanada
Kerasal Topical SolutionUrea (2 %) + Salicylic acid (2 %)LiquidTopicalSpectropharm Dermatology, A Division Of Draxis Health Inc.1992-12-312001-08-13Canada
PedipakUrea + CiclopiroxKitTotal Pharmacy Supply, Inc.2007-09-182016-02-04Us
Psoricare Crm 3%Urea (10 %) + Allantoin (2 %) + Salicylic acid (3 %)CreamTopicalAvacare, Division Of Jeunique International Inc.1984-12-311997-11-10Canada
Sultrin Triple Sulfa CrmUrea (0.64 %) + Sulfabenzamide (3.7 %) + Sulfacetamide (2.86 %) + Sulfathiazole (3.42 %)CreamVaginalOrtho Pharmaceutical, Division Of Janssen Ortho Inc.1946-12-311999-04-14Canada
Thomas Formula No 17Urea (1.7 %) + Benzyl alcohol (.84 %) + Salicylic acid (.4503 %)LiquidTopicalThomas Hair And Scalp Specialists1974-12-311997-01-08Canada
Categories
UNII
8W8T17847W
CAS number
57-13-6
Weight
Average: 60.0553
Monoisotopic: 60.03236276
Chemical Formula
CH4N2O
InChI Key
XSQUKJJJFZCRTK-UHFFFAOYSA-N
InChI
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
IUPAC Name
urea
SMILES
NC(N)=O

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]

Structured Indications
Not Available
Pharmacodynamics

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

Mechanism of action
TargetActionsOrganism
UArginase-1Not AvailableHuman
UCarbonic anhydrase 2Not AvailableHuman
UStructural polyproteinNot AvailableVEEV
UCatenin beta-1Not AvailableHuman
USulfoxide reductase catalytic subunit YedYNot AvailableEscherichia coli O157:H7
UDihydrofolate reductaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Argininosuccinic AciduriaDisease
Hydrochlorothiazide Action PathwayDrug action
Torsemide Action PathwayDrug action
Chlorthalidone Action PathwayDrug action
Triamterene Action PathwayDrug action
Spironolactone Action PathwayDrug action
Prolidase Deficiency (PD)Disease
Lysinuric protein intolerance (LPI)Disease
Arginine and Proline MetabolismMetabolic
Urea CycleMetabolic
Indapamide Action PathwayDrug action
Trichlormethiazide Action PathwayDrug action
Amiloride Action PathwayDrug action
Ornithine Transcarbamylase Deficiency (OTC Deficiency)Disease
Prolinemia Type IIDisease
Hyperprolinemia Type IDisease
D-Arginine and D-Ornithine MetabolismMetabolic
Quinethazone Action PathwayDrug action
Metolazone Action PathwayDrug action
Hartnup DisorderDisease
IminoglycinuriaDisease
ArgininemiaDisease
Blue diaper syndromeDisease
CystinuriaDisease
Citrullinemia Type IDisease
Carbamoyl Phosphate Synthetase DeficiencyDisease
Chlorothiazide Action PathwayDrug action
Ethacrynic Acid Action PathwayDrug action
Hydroflumethiazide Action PathwayDrug action
Furosemide Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB00294
KEGG Drug
D00023
KEGG Compound
C00086
PubChem Compound
1176
PubChem Substance
46508687
ChemSpider
1143
BindingDB
24961
ChEBI
16199
ChEMBL
CHEMBL985
PharmGKB
PA451831
HET
URE
Drugs.com
Drugs.com Drug Page
AHFS Codes
  • 84:28.00 — Keratolytic Agents
  • 40:28.12 — Osmotic Diuretics
PDB Entries
1bv3 / 1ddr / 1ep5 / 1hqg / 1xdq / 1xr8 / 1xr9 / 2f30 / 2f56 / 2i1j
show 55 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedNot AvailableRadiodermatitis1
2TerminatedTreatmentHand-foot Skin Reaction / Rash1
3CompletedPreventionHypertrophic Scars1
3CompletedTreatmentAtopic Dermatitis (AD)1
3Enrolling by InvitationPreventionRadiodermatitis1
3Enrolling by InvitationTreatmentRadiodermatitis1
4CompletedPreventionHand Eczema1
4CompletedTreatmentFoot Dermatoses1
4RecruitingTreatmentChronic Eczema1
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableCompletedTreatmentPsoriasis1
Not AvailableUnknown StatusTreatmentHyperglycemias / Infant, Low Birth Weight1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical100 mg
CreamTopical
CreamTopical10 g/100g
CreamTopical20 g/100g
TabletOral330 mg
SolutionTopical.45 mL/mL
LiquidTopical250 mg/mL
CreamTopical180 mg/mL
CreamTopical100 mg/mL
OintmentTopical.4 g/g
OintmentTopical
LiquidTopical
Kit
CreamTopical71 g/142g
CreamTopical375 mg/g
CreamVaginal
LotionTopical
Aerosol, foamTopical400 mg/g
SuspensionTopical400 mg/g
EmulsionTopical400 mg/g
FilmTopical400 mg/g
Aerosol, foamTopical20 g/100g
LotionTopical450 mg/g
GelTopical.45 mL/mL
ClothTopical450 mg/g
CreamTopical39 g/100g
CreamTopical390 mg/g
CreamTopical40 g/100g
CreamTopical400 mg/g
CreamTopical450 mg/g
CreamTopical500 mg/g
CreamTopical8.5 g/85g
EmulsionTopical50 g/100g
EmulsionTopical500 mg/mL
EmulsionTopical500 mg/g
GelTopical40 g/100mL
GelTopical400 mg/mL
GelTopical450 mg/mL
GelTopical450 mg/g
LotionTopical1 mL/10mL
LotionTopical40 g/100g
LotionTopical40 g/100mL
LotionTopical400 mg/mL
SolutionTopical400 mg/g
SuspensionTopical500 mg/g
CreamTopical470 mg/g
Aerosol, foamTopical35 g/100g
CreamTopical10 %
CreamTopical440 mg/g
CreamTopical410 mg/g
LotionTopical10 %
GelTopical6.726 g/15mL
OintmentTopical7.5 g/30g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)132.7 °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 Solubility412.0 mg/mLALOGPS
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 Area69.11 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.14 m3·mol-1ChemAxon
Polarizability5.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9513
Blood Brain Barrier+0.981
Caco-2 permeable-0.8956
P-glycoprotein substrateNon-substrate0.8517
P-glycoprotein inhibitor INon-inhibitor0.982
P-glycoprotein inhibitor IINon-inhibitor0.9875
Renal organic cation transporterNon-inhibitor0.9343
CYP450 2C9 substrateNon-substrate0.7982
CYP450 2D6 substrateNon-substrate0.793
CYP450 3A4 substrateNon-substrate0.8449
CYP450 1A2 substrateNon-inhibitor0.9661
CYP450 2C9 inhibitorNon-inhibitor0.8771
CYP450 2D6 inhibitorNon-inhibitor0.9878
CYP450 2C19 inhibitorNon-inhibitor0.974
CYP450 3A4 inhibitorNon-inhibitor0.9724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9695
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.6955
BiodegradationReady biodegradable0.5354
Rat acute toxicity0.8822 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.981
hERG inhibition (predictor II)Non-inhibitor0.9824
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0900000000-234545ed5860ba077237
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0079-3900000000-0ef80e5f5cd9dd6bd213
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-02tc-9000000000-d69da17ffbb84fb6bdca
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-234545ed5860ba077237
GC-MS Spectrum - GC-MSGC-MSsplash10-0079-3900000000-0ef80e5f5cd9dd6bd213
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1900000000-d805e3019d86aaf9fec0
Mass Spectrum (Electron Ionization)MSsplash10-02tc-9000000000-871569893ccfa5dd5395
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-9000000000-8f09c5d6f5e002dfa52e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-03dl-9000000000-3d983e9f9115869f55c8
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-9404d66c59d266164c23
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-4bdf0d3bd74007ba840a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-7184b34bac3a316d9fea
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-37fd015e8c20febde95a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-2fc4ec950c571662bb31
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-3443c9c73d9a3f03e398
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-11d83d6bda76c25ec73f
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-9000000000-828ab6c68e3a46ccbd88
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as ureas. These are compounds containing two amine groups joined by a carbonyl (C=O) functional group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic carbonic acids and derivatives
Sub Class
Ureas
Direct Parent
Ureas
Alternative Parents
Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Urea / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Carbonyl group / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
one-carbon compound, isourea (CHEBI:48376) / a small molecule (UREA)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Manganese ion binding
Specific Function
Not Available
Gene Name
ARG1
Uniprot ID
P05089
Uniprot Name
Arginase-1
Molecular Weight
34734.655 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
VEEV
Pharmacological action
Unknown
General Function
Structural molecule activity
Specific Function
Capsid protein possesses a protease activity that results in its autocatalytic cleavage from the nascent structural protein. Following its self-cleavage, the capsid protein transiently associates w...
Gene Name
Not Available
Uniprot ID
P09592
Uniprot Name
Structural polyprotein
Molecular Weight
138349.755 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription regulatory region dna binding
Specific Function
Key downstream component of the canonical Wnt signaling pathway. In the absence of Wnt, forms a complex with AXIN1, AXIN2, APC, CSNK1A1 and GSK3B that promotes phosphorylation on N-terminal Ser and...
Gene Name
CTNNB1
Uniprot ID
P35222
Uniprot Name
Catenin beta-1
Molecular Weight
85495.94 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Escherichia coli O157:H7
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on a sulfur group of donors
Specific Function
The exact function is not known. Can catalyze the reduction of a variety of substrates like dimethyl sulfoxide, trimethylamine N-oxide, phenylmethyl sulfoxide and L-methionine sulfoxide. Cannot red...
Gene Name
yedY
Uniprot ID
Q8XB74
Uniprot Name
Sulfoxide reductase catalytic subunit YedY
Molecular Weight
37356.555 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
folA
Uniprot ID
P0ABQ4
Uniprot Name
Dihydrofolate reductase
Molecular Weight
17999.21 Da
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:17139284]
  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:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Urea transmembrane transporter activity
Specific Function
Specialized low-affinity vasopressin-regulated urea transporter. Mediates rapid transepithelial urea transport across the inner medullary collecting duct and plays a major role in the urinary conce...
Gene Name
SLC14A2
Uniprot ID
Q15849
Uniprot Name
Urea transporter 2
Molecular Weight
101207.965 Da
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:1320335]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Water transmembrane transporter activity
Specific Function
Urea channel that facilitates transmembrane urea transport down a concentration gradient. A constriction of the transmembrane channel functions as selectivity filter through which urea is expected ...
Gene Name
SLC14A1
Uniprot ID
Q13336
Uniprot Name
Urea transporter 1
Molecular Weight
42527.93 Da
References
  1. Ripoche P, Rousselet G: [Urea transporters]. Nephrologie. 1996;17(7):383-8. [PubMed:9019665]
  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:7797558]

Drug created on June 13, 2005 07:24 / Updated on January 14, 2018 10:04