Hydroxyurea (CHEM003724)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-09-11 05:15:44 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003724
Identification
Common NameHydroxyurea
ClassSmall Molecule
DescriptionAn antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antineoplastic Agent
  • Antisickling Agent
  • Drug
  • Enzyme Inhibitor
  • Metabolite
  • Nucleic Acid Synthesis Inhibitor
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Carbamohydroxamic acidChEBI
Carbamohydroximic acidChEBI
Carbamoyl oximeChEBI
Carbamyl hydroxamateChEBI
HidroxicarbamidaChEBI
HydreaChEBI
HydroxycarbamidChEBI
HydroxycarbamideChEBI
HydroxycarbamidumChEBI
HydroxyharnstoffChEBI
N-CarbamoylhydroxylamineChEBI
N-HYDROXYUREAChEBI
OxyureaChEBI
DroxiaKegg
CarbamohydroxamateGenerator
CarbamohydroximateGenerator
Carbamyl hydroxamic acidGenerator
Carbamohydroxyamic acidHMDB
HUHMDB
HydroxicarbamidumHMDB
HydroxycarbamineHMDB
HydroxylureaHMDB
IdrossicarbamideHMDB
OncocarbideHMDB
Chemical FormulaCH4N2O2
Average Molecular Mass76.055 g/mol
Monoisotopic Mass76.027 g/mol
CAS Registry Number127-07-1
IUPAC Namehydroxyurea
Traditional Namehydroxyurea
SMILESNC(=O)NO
InChI IdentifierInChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
InChI KeyVSNHCAURESNICA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassNot Available
Direct ParentCarboximidic acids and derivatives
Alternative Parents
Substituents
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • 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 Point133-136°C
Boiling PointNot Available
Solubility1E+006 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility269 g/LALOGPS
logP-1.8ALOGPS
logP-1.4ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.35 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.91 m³·mol⁻¹ChemAxon
Polarizability5.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0059-3950000000-0418fbb00ea645e9e0ceSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3950000000-0418fbb00ea645e9e0ceSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-be691e1a11d76d687cc5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-725178d2fb4e3ae0a710Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-15e079ef519fdae75dabSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-f39d1396b2b03d5846c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ox-9000000000-b5fb6577ca88b375ebeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-6093ebde62cb84552dd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-5f85466dc663205c60f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-fb233b42b45077d2475dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tf-9000000000-868a329446e04867fc56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-6245f3456e3558782716Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-722afb6d05d2ca0794f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f6792fcc64ed7bdb2466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-fbd92a2a1457de08f558Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-9000000000-ff7708ba70751a23d1ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fd9f25340762315b4515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Toxicity Profile
Route of ExposureWell absorbed from the gastrointestinal tract.
Mechanism of ToxicityHydroxyurea is converted to a free radical nitroxide (NO) in vivo, and transported by diffusion into cells where it quenches the tyrosyl free radical at the active site of the M2 protein subunit of ribonucleotide reductase, inactivating the enzyme. The entire replicase complex, including ribonucleotide reductase, is inactivated and DNA synthesis is selectively inhibited, producing cell death in S phase and synchronization of the fraction of cells that survive. Repair of DNA damaged by chemicals or irradiation is also inhibited by hydroxyurea, offering potential synergy between hydroxyurea and radiation or alkylating agents. Hydroxyurea also increases the level of fetal hemoglobin, leading to a reduction in the incidence of vasoocclusive crises in sickle cell anemia. Levels of fetal hemoglobin increase in response to activation of soluble guanylyl cyclase (sGC) by hydroxyurea-derived NO.
MetabolismHepatic. Route of Elimination: Renal excretion is a pathway of elimination. Half Life: 3-4 hours
Toxicity ValuesOral, mouse: LD50 = 7330 mg/kg; Oral, rat: LD50 = 5760 mg/kg
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesFor management of melanoma, resistant chronic myelocytic leukemia, and recurrent, metastatic, or inoperable carcinoma of the ovary and Sickle-cell anemia.
Minimum Risk LevelNot Available
Health EffectsTeratogenicity: Teratogenic effects have occurred in experimental animals. Hydroxyurea use during a small number of human pregnancies has been reported. Adverse effects have not been observed in any of the exposed newborns. Reproductive Effects: Adverse reproductive effects have occurred in experimental animals. Mutagenicity: Mutagenic effects have occurred in experimental animals.Mutagenic effects have occurred in humans.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01005
HMDB IDHMDB0015140
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDHYDROXY-UREA
METLIN IDNot Available
PDB IDNHY
Wikipedia LinkHydroxyurea
Chemspider ID3530
ChEBI ID44423
PubChem Compound ID3657
Kegg Compound IDC07044
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Dee W. Brooks, Andrew O. Stewart, Richard A. Craig, “Substituted aryl- and heteroarylalkenyl-N-hydroxyurea inhibitors of leukotriene biosynthesis.” U.S. Patent US5506261, issued October, 1990.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11285159
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11298103
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11364534
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11365149
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11391710
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12107454
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14988684
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15772364
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15994344
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16356682
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22983419
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23318979
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23643402
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23696560
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=9271088