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Basic Information
CAS No.: 127-07-1
Name: Hydroxyurea
Article Data: 60
Molecular Structure:
Molecular Structure of 127-07-1 (Hydroxyurea)
Formula: CH4N2O2
Molecular Weight: 76.055
Synonyms: Urea,hydroxy- (6CI,8CI,9CI);Biosupressin;Carbamohydroxamic acid;Carbamohydroximicacid;Carbamoyl oxime;Droxia;Hydrea;Hydreia;Hydroxycarbamide;Hydroxylamine, N-(aminocarbonyl)-;Hydura;Hydurea;Onco-Carbide;Oxyrea;Oxyurea;
EINECS: 204-821-7
Density: 1.457 g/cm3
Melting Point: 135-140 °C
Boiling Point: 136.04°C (rough estimate)
Solubility: water: 50 mg/mL
Appearance: off-white crystalline solid
Hazard Symbols: ToxicT,HarmfulXn
Risk Codes: 46-63-61-40
Safety: 53-36/37-45-36-22
PSA: 75.35000
LogP: 0.13510
Synthetic route
126669-78-1

N-(trimethylsiloxy)-N,N'-bis(trimethylsilyl)urea

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With ethanol96%
126669-76-9

N-(trimethylsiloxy)-N'-(trimethylsilyl)urea

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With ethanol at 20℃; for 15h;94%
1118-02-1

trimethylsilyl isocyanate

4-(1-phenylethoxy)-2-hydroxyacetophenone

A

N-hydroxy-N-[1-(4-(1-phenylethoxy)-2-hydroxyphenyl)-ethyl]urea

B

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With pyridine; hydrogenchloride; hydroxylamine hydrochloride; hydroxylamine In tetrahydrofuran; ethanol; dichloromethane; water; tolueneA n/a
B 78%
598-55-0

methyl carbamate

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With hydroxylamine; sodium hydroxide In water at 20℃; for 3.7h; Time;62.3%
420-05-3

cyanic acid

A

127-07-1

N-hydroxyurea

B

683-62-5

amino carbamate

Conditions
ConditionsYield
With diethyl ether; hydroxylamine
590-28-3

potassium cyanate

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With hydroxylamine sulfate
With hydroxylamine hydrochloride
590-28-3

potassium cyanate

A

127-07-1

N-hydroxyurea

B

683-62-5

amino carbamate

Conditions
ConditionsYield
With hydroxylamine hydrochloride; water
127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With hydroxylamine hydrochloride; water
With Fe(3+), Cu(2+), H2SO4 In not given other Radiation; 20°C; vac.; X-ray irradiatin; concn. of urea 4.6 until 9.1 M in 0.1 N H2SO4;
51-79-6

urethane

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride
With potassium hydroxide; hydroxylamine sulfate
75-13-8

isocyanic acid

127-07-1

N-hydroxyurea

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride
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Consensus Reports

NCI Carcinogenesis Studies (ipr); No Evidence: mouse CANCAR    Cancer. 40 (1977),1935. . NCI Carcinogenesis Studies (ipr); Equivocal Evidence: rat CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Specification

The Hydroxyurea, with the CAS registry number 127-07-1, is also known as Urea, N-hydroxy-. It belongs to the product categories of Miscellaneous Biochemicals; Pharmacetical; Aliphatics; Nucleotides and Nucleosides; Hydroxylamines; Hydroxylamines (N-Substituted); Bases & Related Reagents; Nitric Oxide Reagents; Nucleotides; Carbonyl Compounds; Organic Building Blocks; Ureas; DNA Synthesis Inhibitors; DNA Synthesis Inhibitors Cancer Research; Antitumor Agents; Apoptosis and Cell Cycle; DNA Metabolism; Aids Aided Treatment; Amines. Its EINECS registry number is 204-821-7. This chemical's molecular formula is CH4N2O2 and molecular weight is 76.05. What's more, its IUPAC name is called 1-Hydroxyurea. It should be stored in a cool, dry and well-ventilated place. This chemical can be prepared by Ethyl Carbamate with hydroxylamine hydrochloride.

Physical properties about Hydroxyurea are: (1)ACD/LogP: -1.8; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.80; (4)ACD/LogD (pH 7.4): -1.80; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.50; (8)ACD/KOC (pH 7.4): 2.49; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 75.35 Å2; (13)Index of Refraction: 1.501; (14)Molar Refractivity: 15.376 cm3; (15)Molar Volume: 52.161 cm3; (16)Polarizability: 6.096×10-24 cm3; (17)Surface Tension: 69.72 dyne/cm; (18)Density: 1.458 g/cm3.

Uses of Hydroxyurea: (1) it is used as an anticancer drug; (2) it is used to produce other chemicals. For example, it can react with 2-methyl-3-oxo-butyric acid ethyl ester to get 1-hydroxy-5,6-dimethyl-1H-pyrimidine-2,4-dione. This reaction needs reagent NaOEt and solvent ethanol at ambient temperature. The reaction time is 72 hours. The yield is 60 %.

Hydroxyurea can react with 2-methyl-3-oxo-butyric acid ethyl ester to get 1-hydroxy-5,6-dimethyl-1H-pyrimidine-2,4-dione.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health at low levels and may cause heritable genetic damage. It has a carcinogenic effect and may cause harm to the unborn child. Therefore, you should wear suitable protective clothing and gloves. In addition, you should avoid exposuring and obtain special instructions before using it. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N)NO
(2) InChI: InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
(3) InChIKey: VSNHCAURESNICA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 1gm/kg (1000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
dog LD50 oral > 2gm/kg (2000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
human TDLo intravenous 86mg/kg (86mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: OTHER CHANGES
Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 369, 1973.
human TDLo oral 80mg/kg/D (80mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Cancer Chemotherapy Reports. Vol. 29, Pg. 103, 1963.
man TDLo oral 14mg/kg (14mg/kg)   Annals of Pharmacotherpy. Vol. 29, Pg. 132, 1995.
man TDLo oral 450mg/kg/21D- (450mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"
Netherlands Journal of Medicine. Vol. 51, Pg. 110, 1997.
man TDLo unreported 64mg/kg/3D-I (64mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: COUGH
Australian and New Zealand Journal of Medicine. Vol. 28, Pg. 347, 1998.
mouse LD10 subcutaneous 2400mg/kg (2400mg/kg)   European Journal of Cancer. Vol. 10, Pg. 667, 1974.
mouse LD50 intraperitoneal 5800mg/kg (5800mg/kg)   Cancer Research. Vol. 39, Pg. 3575, 1979.
mouse LD50 intravenous 2350mg/kg (2350mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
mouse LD50 oral 7330mg/kg (7330mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 intraperitoneal > 4700mg/kg (4700mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 645, 1968.
rat LD50 intravenous 4730mg/kg (4730mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 oral 5760mg/kg (5760mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 unreported 4300mg/kg (4300mg/kg)   Proceedings of the American Association for Cancer Research. Vol. 4, Pg. 10, 1963.
women TDLo oral 600mg/kg/30D- (600mg/kg)   Netherlands Journal of Medicine. Vol. 51, Pg. 110, 1997.
women TDLo oral 600mg/kg/30D- (600mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Netherlands Journal of Medicine. Vol. 51, Pg. 110, 1997.