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H8627

Sigma-Aldrich

Hydroxyurea

98% (elemental analysis), powder, RNR inhibitor

Synonym(s):

Hydroxycarbamide

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About This Item

Linear Formula:
NH2CONHOH
CAS Number:
127-07-1
Molecular Weight:
76.05
Beilstein/REAXYS Number:
1741548
EC Number:
204-821-7
MDL number:
MFCD00007943
UNSPSC Code:
12352200
PubChem Substance ID:
24278474
NACRES:
NA.77

product name

Hydroxyurea, 98%, powder

assay

98%

form

powder

color

white

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

SMILES string

NC(=O)NO

InChI

1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)

InChI key

VSNHCAURESNICA-UHFFFAOYSA-N

Gene Information

human ... CA1(759) , CA2(760) , CYP1A2(1544) , RRM1(6240) , RRM2(6241) , RRM2B(50484)

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General description

Hydroxyurea is a hydroxylated analog of urea. It is beneficial in increasing fetal hemoglobin (HbF) levels, which in turn reduces the frequency of severe crises and the need for blood transfusions in sickle cell anemia patients. Hydroxyurea exhibits cell-cycle specificity for the S phase, leading to cell arrest at G1 to S. This non-alkylating S phase-specific myelosuppressive agent has a mechanism of action that is not specific to platelets.

Application

Hydroxyurea has been used:
  • for cell cycle synchronization in MCF-7 human breast carcinoma cells, Schizosaccharomyces pombe, primary root of seedling
  • as a drug for treating the parasite Leishmania mexicana in cell viability and cell cycle assay
  • as an inhibitor in the cell adhesion and motility assay in Caki control and CD9 knockdown cells

Biochem/physiol Actions

Anti-neoplastic. Inactivates ribonucleoside reductase by forming a free radical nitroxide that binds a tyrosyl free radical in the active site of the enzyme. This blocks the synthesis of deoxynucleotides, which inhibits DNA synthesis and induces synchronization or cell death in S-phase.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H340,H361

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Flow cytometric chromosome sorting in plants: the next generation
Vrana J, et al.
Methods, 57(3), 331-337 (2012)
Hydroxyurea Toxicity
Jinna S and Khandhar PB
StatPearls [Internet] (2019)
The utility of tetraspanin CD9 as a biomarker for metastatic clear cell renal cell carcinoma
Garner JM, et al.
Biochemical and Biophysical Research Communications, 471(1), 21-25 (2016)
Mus81, Rhp51(Rad51), and Rqh1 form an epistatic pathway required for the S-phase DNA damage checkpoint.
Willis N and Rhind N
Molecular Biology of the Cell, 20(3), 819-833 (2009)
Protein tyrosine nitration in the cell cycle
Jia M, et al.
Biochemical and Biophysical Research Communications, 413(2), 270-276 (2011)
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Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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