Urea C-13

Identification

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Name
Urea C-13
Accession Number
DB09510
Type
Small Molecule
Groups
Approved
Description

Urea 13C is a urea molecule radiolabelled with the non-radioactive element carbon-13. It is currently used for the Urea Breath Test (UBT) and is available as a rapid diagnostic test (marketed as Pranactin-Citric) for the detection of Helicobacter pylori infections. H pylori is a common stomach bacteria that has been linked to a variety of upper gastrointestinal disorders such as gastritis, gastric and peptic ulcers, stomach cancer, and gastric mucosa-associated lymphoid-tissue (MALT) lymphoma. The UBT is indicated to confirm H. pylori infection and to monitor post-treatment for its eradication.

Radiolabelled urea is available in two forms as 13C and 14C. Both forms can be used within the Urea Breath Test, however some may prefer 13C as it is non-radioactive compared to 14C, which may be preferable in pregnant women and children.

The Urea Breath Test is based on the ability of the H. pylori enzyme urease to cleave urea into ammonia and carbon dioxide. As the urease enzyme is not present in mammalian cells, the presence of urease (and the products of urea cleavage) in the stomach is evidence that H. pylori bacteria are present. To detect H. pylori, urea labeled with 13C is swallowed by the patient. If gastric urease from H. pylori is present, urea is split to form CO2 and NH3 at the interface between the gastric epithelium and lumen and 13CO2 is absorbed into the blood and exhaled in the breath. Exhaled breath samples can then be collected and measured for the presence of radioactivity.

Structure
Thumb
Synonyms
  • (13C)urea
  • 13C-urea
  • Carbon 13 urea
  • Carbon-13 urea
  • Urea (13C)
  • Urea 13 C
  • Urea C 13
  • Urea-13C
  • Urea, C-13
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Helicobacter Test InfaiPowder, for solution75 mgOralInfai, Institut Für Biomedizinische Analytik & Nmr Imaging Gmb H1997-08-14Not applicableEu
Helicobacter Test InfaiPowder, for solution75 mgOralInfai, Institut Für Biomedizinische Analytik & Nmr Imaging Gmb H1997-08-14Not applicableEu
Helicobacter Test InfaiPowder, for solution75 mgOralInfai, Institut Für Biomedizinische Analytik & Nmr Imaging Gmb H1997-08-14Not applicableEu
Helicobacter Test InfaiPowder, for solution75 mgOralInfai, Institut Für Biomedizinische Analytik & Nmr Imaging Gmb H1997-08-14Not applicableEu
Helicobacter Test Infai for Children Of The Age 3-11Powder, for solution45 mgOralInfai, Institut Für Biomedizinische Analytik & Nmr Imaging Gmb H1997-08-14Not applicableEu
Pranactin-CitricPowder, for solution75 mg/3000mgOralOtsuka Pharmaceutical Co., Ltd.2001-05-10Not applicableUs
PylobactellTablet100 mgOralTorbet Laboratories Limited1998-05-07Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
IDkit HP ONEUrea C-13 (75 mg/1) + Citric acid monohydrate (4 g/1)KitOralExalenz Bioscience Ltd.2009-12-28Not applicableUs
Categories
UNII
W6KX9E6D8X
CAS number
Not Available
Weight
Average: 61.048
Monoisotopic: 61.035717592
Chemical Formula
CH4N2O
InChI Key
XSQUKJJJFZCRTK-OUBTZVSYSA-N
InChI
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)/i1+1
IUPAC Name
(13C)carbamimidic acid
SMILES
N[13C](O)=N

Pharmacology

Indication

Urea-13C is indicated for use in the qualitative detection of urease associated with Helicobacter pylori in the human stomach and as an aid in the initial diagnosis and post-treatment monitoring of Helicobacter pylori infection in adult patients. The test may be used for monitoring treatment if used at least four (4) weeks following completion of therapy. For these purposes, the system utilizes an Infrared Spectrophotometer for the measurement of the ratio of 13CO2 to 12CO2 in breath samples.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

The Urea Breath Test is based on the ability of the H. pylori enzyme urease to cleave urea into ammonia and carbon dioxide. As the urease enzyme is not present in mammalian cells, the presence of urease (and the products of urea cleavage) in the stomach is evidence that H. pylori bacteria are present. To detect H. pylori, urea labeled with 13C is swallowed by the patient. If gastric urease from H. pylori is present, urea is split to form CO2 and NH3 at the interface between the gastric epithelium and lumen and 13CO2 is absorbed into the blood and exhaled in the breath. Exhaled breath samples can then be collected and measured for the presence of radioactivity.

TargetActionsOrganism
AUrease
substrate
Helicobacter pylori
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Ferwana M, Abdulmajeed I, Alhajiahmed A, Madani W, Firwana B, Hasan R, Altayar O, Limburg PJ, Murad MH, Knawy B: Accuracy of urea breath test in Helicobacter pylori infection: meta-analysis. World J Gastroenterol. 2015 Jan 28;21(4):1305-14. doi: 10.3748/wjg.v21.i4.1305. [PubMed:25632206]
  2. Raju GS, Smith MJ, Morton D, Bardhan KD: Mini-dose (1-microCi) 14C-urea breath test for the detection of Helicobacter pylori. Am J Gastroenterol. 1994 Jul;89(7):1027-31. [PubMed:8017360]
External Links
KEGG Drug
D01749
PubChem Compound
636363
PubChem Substance
347827869
ChemSpider
552162
ChEBI
32285
ChEMBL
CHEMBL2096648
Wikipedia
Urea_breath_test
FDA label
Download (3.98 MB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Powder, for solutionOral75 mg
Powder, for solutionOral45 mg
KitOral
Powder, for solutionOral75 mg/3000mg
TabletOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.8 mg/mLALOGPS
logP-1.5ALOGPS
logP-2.1ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)0.55ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area70.1 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.2 m3·mol-1ChemAxon
Polarizability5.13 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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
urea (CHEBI:32285)

Targets

Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Yes
Actions
Substrate
General Function
Not Available
Specific Function
Nickel cation binding
Gene Name
ureB
Uniprot ID
Q8KT33
Uniprot Name
Urease
Molecular Weight
40196.87 Da

Drug created on November 30, 2015 12:10 / Updated on July 13, 2019 00:54