hydroxyurea

• ChemBase ID: 878
• Molecular Formular: CH4N2O2
• Molecular Mass: 76.05466
• Monoisotopic Mass: 76.02727738
• SMILES: ONC(=O)N
• Canonical SMILES: NC(=O)NO
• InChI: InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
• InChIKey: VSNHCAURESNICA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hydroxyurea
• IUPAC Traditional name: hydroxyurea
• Brand Name: Biosupressin; Droxia; Hidrix; Hydrea; Hydreia; Hydura; Hydurea; Litaler; Litalir; Onco-Carbide; Oxyurea; Ureaphil
• Synonyms: Hydroxyurea; N-HYDROXY UREA; 1-hydroxyurea; Carrbamoyl Oxime; N-(Aminocarbonyl) Hydroxyamine; Oxyurea; Hydrea; Biosupressin; Cytodrox; Carbamoyl Oxime; Carbamyl Hydroxamate; HU; Hydroxicarbamidum; Hydroxycarbamide; Hydroxycarbamine; Hydroxylurea; Idrossicarbamide [Dcit]; Carbamohydroxamic Acid; Carbamohydroximic Acid; Carbamohydroxyamic Acid; N-Carbamoylhydroxylamine; N-Hydroxyurea; Sterile Urea; Hydroxyurea; Hydroxyurea 99%; Droxia; Hidrix; Hydreia; N-(Aminocarbonyl)hydroxylamine; Hydura; Hydurea; Litaler; Litalir; NCI C04831; NSC 32065; SK 22591; SQ 1089; Hydroxy Urea; 羟基脲

Database IDs

• CAS Number: 127-07-1
• EC Number: 204-821-7
• MDL Number: MFCD00007943
• Beilstein Number: 1741548
• Merck Index: 144848
• PubChem SID: 24278474; 46506927; 24879294; 160964341
• PubChem CID: 3657

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.140479
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -1.3670254
• LogD (pH = 7.4): -1.3677943
• Log P: -1.3670156
• Molar Refractivity: 14.9072 cm^3
• Polarizability: 5.76081 Å^3
• Polar Surface Area: 75.35 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.83
• LOG S: 0.55
• Solubility (Water): 2.69e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1E+006 mg/L; DMSO; H2O: soluble50 mg/mL; Water
• Apperance: Off-White Solid; white powder
• Melting Point: 133-136°C (dec.); 133-136°C; 135°C; 135-140 °C; ca 140°C dec.
• Hydrophobicity(logP): -1.6; -1.8

Safety Information

• Storage Condition: -20°C; 2-8°C; Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Toxic/Moisture Sensitive
• RTECS: YT4900000
• European Hazard Symbols: Toxic (T); Irritant (Xi); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 46-61; 46-63; R:36/37/38-40-46
• Safety Statements: 53-20-36-45; 53-36/37-45; S:20-25-26-37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 否
• GHS Pictograms: GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H340-H360; H340-H361; H361
• GHS Precautionary statements: P201-P281-P308 + P313; P281; P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760), CYP1A2(1544), RRM1(6240)

Product Information

• Purity: ≥98% (TLC); ≥98.0% (N); 95%; 95+%; 98%
• Salt Data: Free Base
• Linear Formula: NH2CONHOH

DETAILS

MP Biomedicals - 05223590

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102023

Crystalline
Inhibitor of DNA synthesis.

DrugBank - DB01005

• Drug Groups: approved
• Description: An antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase. [PubChem]
• Indication: For management of melanoma, resistant chronic myelocytic leukemia, and recurrent, metastatic, or inoperable carcinoma of the ovary and Sickle-cell anemia.
• Pharmacology: Hydroxyurea has dose-dependent synergistic activity with cisplatin in vitro. In vivo Hydroxyurea showed activity in combination with cisplatin against the LX-1 and CALU-6 human lung xenografts, but minimal activity was seen with the NCI-H460 or NCI-H520 xenografts. Hydroxyurea was synergistic with cisplatin in the Lewis lung murine xenograft. Sequential exposure to Hydroxyurea 4 hours before cisplatin produced the greatest interaction.
• Toxicity: Oral, mouse: LD₅₀ = 7330 mg/kg; Oral, rat: LD₅₀ = 5760 mg/kg; Teratogenicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Well absorbed from the gastrointestinal tract.
• Half Life: 3-4 hours
• Elimination: Renal excretion is a pathway of elimination.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1896

Research Area: Cancer
Biological Activity:
Hydroxyurea(Cytodrox) is an antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase. Hydroxyurea 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. [1]

Sigma Aldrich - H8627

包装
1, 5, 10, 25, 100 g in poly bottle
Biochem/physiol Actions
抗肿瘤剂。通过形成自由基硝基氧灭活核糖核苷还原酶，自由基硝基氧可结合到酶活性位点的酪氨酰自由基。这可阻断脱氧核苷酸的合成，从而抑制 DNA 合成，并且诱导细胞周期同步化或 S-期细胞死亡。

Sigma Aldrich - 115207

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.

Sigma Aldrich - 55291

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.

Toronto Research Chemicals - H991000

An anti-neoplastic - inhibits ribonucleoside reductase and DNA replication. A potential therapy for sickle cell anemia which involves the nitrosylation of sickle cell hemoglobin. Horseradish peroxidase catalyzes nitric oxide formation from hydroxyurea in

REFERENCES

• http://www.drugbank.ca/drugs/DB01005
• Ratcliffe, W., et al.: Lancet, 339, 164 (1992)
• Roodman, G., et al.: Cancer, 80, 1557 (1992)
• Horwitz, M., et al.: J. Clin. Endocrinol. Metab., 2003, 88, 1603 (1992)