115207
Hydroxyurea
98%
Synonym(s):
Hydroxycarbamide
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About This Item
Linear Formula:
NH2CONHOH
CAS Number:
Molecular Weight:
76.05
EC Number:
204-821-7
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
1741548
InChI
1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
InChI key
VSNHCAURESNICA-UHFFFAOYSA-N
SMILES string
NC(=O)NO
assay
98%
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Application
Inhibitor of DNA synthesis.
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.
Regulatory Information
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Carl E Wagner et al.
Journal of medicinal chemistry, 52(19), 5950-5966 (2009-10-02)
This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use
Hugo Martinez-Rojano et al.
Antimicrobial agents and chemotherapy, 52(10), 3642-3647 (2008-08-13)
Leishmania mexicana is a protozoan parasite that causes a disease in humans with frequent relapses after treatment. It is also highly resistant to the currently available drugs. For this reason, there is an urgent need for more effective antileishmanial drugs.
Kesavan Krishnan et al.
Bioorganic & medicinal chemistry letters, 18(23), 6248-6250 (2008-11-04)
Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1:1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were
Howard M Stern et al.
Nature chemical biology, 1(7), 366-370 (2005-12-24)
Bmyb is a ubiquitously expressed transcription factor involved in cellular proliferation and cancer. Loss of bmyb function in the zebrafish mutant crash&burn (crb) results in decreased cyclin B1 expression, mitotic arrest and genome instability. These phenotypic observations in crb mutants
Claudia Temperini et al.
Bioorganic & medicinal chemistry letters, 16(16), 4316-4320 (2006-06-09)
N-Hydroxyurea binds both to carbonic anhydrase (CA) and to matrix metalloproteinases (MMPs). X-ray crystallography showed N-hydroxyurea to bind in a bidentate mode by means of the oxygen and nitrogen atoms of the NHOH moiety to the Zn(II) ion of CA
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