Diazolidinyl urea (T3D3626)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-11-23 23:08:08 UTC
Update Date2014-12-24 20:26:14 UTC
Accession NumberT3D3626
Identification
Common NameDiazolidinyl urea
ClassSmall Molecule
DescriptionDiazolidinyl urea is an antimicrobial preservative that acts as a formaldehyde releaser. It is used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben. Diazolidinyl urea may cause contact dermatitis. Its toxicity is also due to it's ability to release formaldehyde, which is believed to be carcinogenic. (3)
Compound Type
  • Amide
  • Amine
  • Cosmetic Toxin
  • Household Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Diazolidinylurea
Germall 11
Germall II
Imidazolidinyl urea 11
N-(1,3-Bis(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl)-N,n'-bis(hydroxymethyl) urea
Chemical FormulaC8H14N4O7
Average Molecular Mass278.219 g/mol
Monoisotopic Mass278.086 g/mol
CAS Registry Number78491-02-8
IUPAC Name1-[1,3-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1,3-bis(hydroxymethyl)urea
Traditional Namediazolidinyl urea
SMILESOCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O
InChI IdentifierInChI=1S/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18)
InChI KeyInChIKey=SOROIESOUPGGFO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as allantoins. These are heterocyclic compounds containing an imiazolidine ring substituted by a ketone group at positions 2 and 5, and an urea at position 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentAllantoins
Alternative Parents
Substituents
  • Allantoin
  • Alpha-amino acid or derivatives
  • Ureide
  • N-acyl urea
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Alkanolamine
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1000 mg/mL at 25°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility29.1 g/LALOGPS
logP-2.2ALOGPS
logP-3.8ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.88 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.02 m³·mol⁻¹ChemAxon
Polarizability24.28 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-145fdee36d825d8eb8f02016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-0970000000-c286f9a082ee211e393e2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0930000000-fe1c7215f52092ff48e72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016s-0190000000-2ae8acf690107ac94f312016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2090000000-c8ec0d76384135b500892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-4920000000-3b81c399001b1e89090b2016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityDiazolidinyl urea is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (2, 3)
MetabolismFormaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans (for formaldehyde). (1)
Uses/SourcesDiazolidinyl urea is an antimicrobial preservative used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben. (3)
Minimum Risk LevelNot Available
Health EffectsDiazolidinyl urea releases formaldehyde, a known human carcinogen. (2, 3)
SymptomsSome people have a contact allergy to diazolidinyl urea, causing dermatitis. (3)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID62277
ChEMBL IDNot Available
ChemSpider ID56078
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDiazolidinyl_urea
References
Synthesis ReferenceNot Available
MSDST3D3626.pdf
General References
  1. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  2. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  3. Wikipedia. Diazolidinyl urea. Last Updated 29 October 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. RNA
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. Diazolidinyl urea. Last Updated 29 October 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. Diazolidinyl urea. Last Updated 29 October 2009. [Link]
Target Details
3. Androgen receptor
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.10 uMOT_AR_ARSRC1_0960Odyssey Thera
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]