N-Hydroxyurea
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04547 |
| CAS | 127-07-1 |
| Molecular Weight | 76.05 |
| Molecular Formula | CH4N2O2 |
| Purity | >98% |
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Description
Hydroxyurea is an antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase.
Specification
| Synonyms | NSC-32065; Hydroxycarbamide; Hydrea; 1-Hydroxyurea; Oxyurea; Biosupressin; Carbamohydroxamic acid; Litalir; N-Carbamoylhydroxylamine; Droxia; Siklos; Carbamoyl Oxime; Cytodrox; Hidrix |
| Storage | Store at 2-8°C under inert atmosphere |
| IUPAC Name | hydroxyurea |
| Canonical SMILES | C(=O)(N)NO |
| InChI | InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4) |
| InChI Key | VSNHCAURESNICA-UHFFFAOYSA-N |
Properties
| Appearance | White to Off-white Solid |
| Application | Antineoplastic agents; antisickling agents; enzyme inhibitors; nucleic acid synthesis inhibitors |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 136.04°C (Predicted) |
| Melting Point | 133-136°C (dec.) |
| Flash Point | 88.1±22.6 °C |
| Density | 1.457±0.06 g/cm3 (Predicted) |
| Solubility | Slightly soluble in DMSO, Water |
| LogP | -1.8 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | 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. |
| Toxicity | LD50 = 7330 mg/kg (Oral, mouse); LD50 = 5760 mg/kg (Oral, rat). |
Reference Reading
1.Ingenol mebutate in the treatment of 'Hydroxyurea-induced Squamous Dysplasia': a single centre experience.
Grandi V1, Delfino C1, Pimpinelli N1. J Eur Acad Dermatol Venereol. 2016 Apr 13. doi: 10.1111/jdv.13616. [Epub ahead of print]
BACKGROUND: 'Hydroxyurea-induced Squamous Dysplasia' (HISD) is a cutaneous side-effect related to chronic oral treatment with Hydroxyurea. Ingenol mebutate gel is a topical drug approved for the treatment of multiple, non-hypertrophic actinic keratoses (AK) localized within a limited cancerization field. Since HISD may be considered as a drug-induced variant of classic AK, ingenol mebutate is likely to have therapeutic effects.
2.Hydroxyurea for Treatment of Nephrotic Syndrome Associated With Polycythemia Vera.
Hundemer GL1, Rosales IA2, Chen YB3, Colvin RB2, Tolkoff-Rubin NE4. Am J Kidney Dis. 2016 Apr 29. pii: S0272-6386(16)30023-3. doi: 10.1053/j.ajkd.2016.02.056. [Epub ahead of print]
Myeloproliferative disorders are a rare cause of focal segmental glomerulosclerosis (FSGS), although the mechanism is unclear. Hydroxyurea is commonly used in these disorders for its cytoreductive properties; however, the effect of this treatment on proteinuria or kidney function remains unclear in cases of myeloproliferative disorder-associated FSGS. We describe the clinical course of a patient with polycythemia vera and nephrotic-range proteinuria, demonstrated to have FSGS on biopsy. The patient had a distant history of granulomatosis with polyangiitis (Wegener's), for which he routinely had his kidney function and proteinuria measured, allowing for early detection of nephrotic syndrome soon after being diagnosed with polycythemia vera. Treatment with hydroxyurea resulted in rapid improvement in proteinuria that correlated with a decrease in hematocrit. This response was replicated 2 additional times when the patient was taken off and then restarted on hydroxyurea therapy.
Spectrum
GC-MS Spectrum - GC-MS (3 TMS)
Experimental Conditions
Instrument Type: GC-MS
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 1226.93
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Derivative Type: 3 TMS
Derivative Formula: C10H28N2O2Si3
Derivative Molecular Weight: 292.598
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 1226.93
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Derivative Type: 3 TMS
Derivative Formula: C10H28N2O2Si3
Derivative Molecular Weight: 292.598
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: CH4N2O2
Molecular Weight (Monoisotopic Mass): 76.0273 Da
Molecular Weight (Avergae Mass): 76.0547 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: CH4N2O2
Molecular Weight (Monoisotopic Mass): 76.0273 Da
Molecular Weight (Avergae Mass): 76.0547 Da
LC-MS/MS Spectrum - LC-ESI-QQ , positive
Experimental Conditions
Instrument Type: LC-ESI-QQ
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: CH4N2O2
Molecular Weight (Monoisotopic Mass): 76.0273 Da
Molecular Weight (Avergae Mass): 76.0547 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: CH4N2O2
Molecular Weight (Monoisotopic Mass): 76.0273 Da
Molecular Weight (Avergae Mass): 76.0547 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
