hydroxyurea

• ChemBase编号: 878
• 分子式: CH4N2O2
• 平均质量: 76.05466
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: hydroxyurea
• IUPAC传统名: hydroxyurea
• 商标名: Biosupressin; Droxia; Hidrix; Hydrea; Hydreia; Hydura; Hydurea; Litaler; Litalir; Onco-Carbide; Oxyurea; Ureaphil
• 别名: 羟基脲; 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

登记号

• CAS号: 127-07-1
• EC号: 204-821-7
• MDL号: MFCD00007943
• Beilstein号: 1741548
• 默克索引号: 144848
• PubChem SID: 24278474; 46506927; 24879294; 160964341
• PubChem CID: 3657

理论计算性质

JChem

• Acid pKa: 10.140479
• 质子受体: 2
• 质子供体: 3
• LogD (pH = 5.5): -1.3670254
• LogD (pH = 7.4): -1.3677943
• Log P: -1.3670156
• 摩尔折射率: 14.9072 cm^3
• 极化性: 5.76081 Å^3
• 极化表面积: 75.35 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.83
• LOG S: 0.55
• 溶解度: 2.69e+02 g/l

分子性质

理化性质

• 溶解度: 1E+006 mg/L; DMSO; H2O: soluble50 mg/mL; Water
• 外观: Off-White Solid; white powder
• 熔点: 133-136°C (dec.); 133-136°C; 135°C; 135-140 °C; ca 140°C dec.
• 疏水性(logP): -1.6; -1.8

安全信息

• 保存条件: -20°C; 2-8°C; Hygroscopic, Refrigerator, Under Inert Atmosphere
• 保存注意事项: Toxic/Moisture Sensitive
• RTECS编号: YT4900000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 澳大利亚Hazchem: 2X
• 危险公开号: 46-61; 46-63; R:36/37/38-40-46
• 安全公开号: 53-20-36-45; 53-36/37-45; S:20-25-26-37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• TSCA收录: 否
• GHS危险品标识: GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H340-H360; H340-H361; H361
• GHS警示性声明: P201-P281-P308 + P313; P281; P281-P201-P202-P308+P313-P405-P501A
• 个人保护装置: 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
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CA1(759), CA2(760), CYP1A2(1544), RRM1(6240)

产品相关信息

• 纯度: ≥98% (TLC); ≥98.0% (N); 95%; 95+%; 98%
• 成盐信息: Free Base
• 线性分子式: NH2CONHOH

详细说明

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
DNA 合成抑制剂。
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 - 55291

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。

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

参考文献

• 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)