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51-21-8

51-21-8 Structure

51-21-8 Structure
IdentificationMore
[Name]

5-Fluorouracil
[CAS]

51-21-8
[Synonyms]

1-FLUORO-1H-PYRIMIDINE-2,4-DIONE
2,4-DIHYDROXY-5-FLUOROPYRIMIDINE
5-FLUORO-1H-PYRIMIDINE-2,4-DIONE
5-FLUORO-2,4(1H,3H)-PYRIMIDINEDIONE
5-FLUORO-2,4-DIHYDROXYPYRIMIDINE
5-fluoro-2,4-pyrimidinedione
5-FLUOROPYRIMIDINE-2,4(1H,3H)-DIONE
5-Fluoropyrimidine-2,4-dione
5-FLUOROURACIL
5-FU
FLUOROURACIL
FU
[180]-5-Fluorouracil
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
2,4-dioxo-5-fluoropyrimidine
3h)-pyrimidinedione,5-fluoro-4(1h
5-faracil
5-Flouracyl
5-fluor-2,4(1h,3h)-pyrimidindion
5-Fluor-2,4-dihydroxypyrimidin
[EINECS(EC#)]

200-085-6
[Molecular Formula]

C4H3FN2O2
[MDL Number]

MFCD00006018
[Molecular Weight]

130.08
[MOL File]

51-21-8.mol
Chemical PropertiesBack Directory
[Appearance]

Crystalline
[Appearance]

Fluorouracil is a white crystalline solid. Practically odorless.
[mp ]

282-286 °C (dec.)(lit.)
[bp ]

190-200°C/0.1mmHg
[storage temp. ]

Store at 0-5
[solubility ]

H2O: 10 mg/mL, clear
[form ]

powder
[color ]

white
[Stability:]

Stable. Light sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases.
[Water Solubility ]

12.2 g/L 20 ºC
[Usage]

A potent antineoplastic agent in clinical use. Also an inhibitor of DNA synthesis
[Sensitive ]

Air Sensitive
[Merck ]

14,4181
[Detection Methods]

HPLC,NMR
[BRN ]

127172
[CAS DataBase Reference]

51-21-8(CAS DataBase Reference)
[NIST Chemistry Reference]

2,4-Pyrimidinedione, 5-fluoro-(51-21-8)
[EPA Substance Registry System]

51-21-8(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn,T,C,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

YR0350000
[F ]

10-23
[Hazard Note ]

Irritant/Highly Toxic
[TSCA ]

T
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

29335995
[Safety Profile]

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by parented and rectal routes. Experimental teratogenic and reproductive effects. Human systemic effects: EKG changes, bone marrow changes, cardiac, pulmonary, and gastrointestinal effects. Human mutation data reported. A human skin irritant. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of Fand NOx.
[Hazardous Substances Data]

51-21-8(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium methanolate-->Ethyl formate -->Ethyl fluoroacetate
[Preparation Products]

4-Amino-2-chloro-5-fluoropyrimidine-->Fluorocytosine-->Tegafur-->O,O'-BIS(TRIMETHYLSILYL)-5-FLUOROURACIL-->2,4-Dichloro-5-fluoropyrimidine-->2,4-DICHLORO-6-FLUOROPYRIMIDINE-->Floxuridine
Hazard InformationBack Directory
[General Description]

White to nearly white crystalline powder; practically odorless. Used as an anti neoplastic drug, chemosterilant for insects.
[Reactivity Profile]

FLUOROURACIL(51-21-8) may be sensitive to prolonged exposure to light. Solutions discolor on storage. This chemical can react with oxidizing agents and strong bases. Incompatible with methotrexate sodium.
[Air & Water Reactions]

Insoluble in water.
[Hazard]

Questionable carcinogen.
[Health Hazard]

Minimum toxic dose in humans is approximately 450 mg/kg (total dose) over 30 days for the ingested drug. Intravenous minimum toxic dose in humans is a total dose of 6 mg/kg over three days. Depression of white blood cells occurred after intravenous administrative of a total dose of 480 mg/kg over 32 days. Occasional neuropathy and cardiac toxicity have been reported. Do not use during pregnancy. Patients with impaired hepatic or renal function, with a history of high-dose pelvic irradiation or previous use of alkylating agents should be treated with extreme caution. Patients with nutritional deficiencies and protein depletion have a reduced tolerance to fluorouracil.
[Potential Exposure]

This material is used as an antineo plastic drug for cancer treatment and as a chemosterilant for insects.
[Fire Hazard]

Emits very toxic fumes of flourides and nitrogen oxides when heated to decomposition. Avoid decomposing heat.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Keep victim quiet and maintain normal body temperature.
[Shipping]

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
[Incompatibilities]

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, methotrexrate sodium, sources of heat.
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

5-Fluoropyrimidine-2,4-dione(51-21-8).msds
Questions And AnswerBack Directory
[Antimetabolite]

5-fluorouracil is short for fluorouracil, and is pyrimidine antimetabolites, 5-fluorouracil as fluorouracil for pyrimidine antimetabolites, is currently clinically commonly used a chemotherapy drug, having effect on proliferation, can prevent the thymine formation, inhibition of DNA biosynthesis, thereby inhibiting the growth of cancer cells. Clinically, it is used to treat gastrointestinal tumors, such as stomach cancer, colon cancer, liver cancer and so on. In breast cancer, ovarian cancer, lung cancer, bladder cancer, cervical cancer, pancreatic cancer and so on are also effective. The Swiss production of skin cancer treatment ointment containing 5% of the goods, mainly used for actinic keratoses and senile keratosis, precancerous dermatitis, single and multiple shallow table basal cell carcinoma, radioactive skin lesion of carcinoma and superficial basal cell carcinoma.
5-fluorouracil first changes for 5-Fluoro 2 deoxy urea pyrimidine nucleotides in vivo and inhibition of thymidylate synthase, blocking the transformation of urea pyrimidine deoxyribonucleotide thymidine, which affects DNA biosynthesis. At the same time, it can be incorporation into RNA by blocking urea ethyl pyridine and whey acid was incorporated into the RNA to direct inhibition of RNA synthesis.
This medicine is mainly in the liver metabolism, most of the decomposed into carbon dioxide discharged from breathing, rarely excreted from urine. After oral, absorption is different; vein after administration, concentrations in plasma quickly drop in two hours; static note within 30 minutes can arrive in cerebrospinal fluid (CSF) and maintain for 3 hours; continuous intravenous infusion toxicity is lighter than intravenous injection; vein to the drug's effect is compared with oral high. Toxicity of 5-fluorouracil on the proliferation is greater than non proliferating cells, but no obvious cell cycle specificity. Resistance to 5-FU can increase essential activity of enzyme missing or thymidylate synthetase activity.
The above information is edited by the Chemicalbook Hayan.
[Pharmacokinetics]

Due to the instability of the absorption of 5-fluorouracil, the conventional the oral (in Europe can be obtained from oral preparation). General intravenous administration, We can also take transarterial Administration in order to directly reach the tumor (e.g. liver metastasis through hepatic artery) and injected directly into the body cavity infiltration liquid (such as ovarian cancer). Intravenous injection plasma half-life is 7.5~10 minutes, after 3 hours the drug in the plasma has not check did not change. Intracellular drug levels are last much longer.
Fluorouracil in the liver is used for metabolism; 60~80% in 8~12 hours as a respiratory carbon dioxide discharge and 15% in 6 hours technical unchanged from the urine discharge. The drug can enter into the exudate and cerebrospinal fluid (CSF). It has existed determination method for plasma fluorouracil.
[Indications]

It is clinical for breast cancer, digestive tract cancer, ovarian cancer and primary bronchogenic lung adenocarcinoma adjuvant chemotherapy and palliative care; is also in the treatment of malignant hydatidiform mole, choriocarcinoma, serous cancer of effusion in bladder cancer and head and neck malignant tumor and liver cancer chemotherapy drugs.
Dermatological topical containing 5% 5-fluorouracil ointment is used in the treatment of actinic keratosis, actinic cheilitis, Bowen's disease, erythroplasia of Queyrat, Bowenoid papulosis, condyloma acuminatum, vitiligo, lichen amyloidosis, disseminated superficial porokeratosis, warts, flat warts, psoriasis, color of dry skin disease, superficial basal cell epithelioma table etc.; intralesional injection in the treatment of keratoacanthoma keloid.
[Drug interaction]

Before using this drug, first it is used methotrexate, 5-fluorouracil nucleotide formation is increased by increasing the content of intracellular phosphoribosyl pyrophosphate. Allopurinol can change the role of fluorouracil. Its metabolites, oxypurinol, can inhibit orotate phosphoribosyl transferase and thus reduce the toxicity and may improve the therapeutic index. Increase in thymidine and other nucleoside combination of fluorouracil and RNA and thymidine by dihydropyrimidine dehydrogenase can delay fluorouracil decomposition. However, the drug combination did not significantly improve the clinical effect so far.
[Adverse reactions and precautions]

The main toxic effect of fluorouracil is involving the gastrointestinal tract and blood cell generation system. Anorexia, nausea and vomiting were common. Stomatitis, pharyngo esophageal inflammation and diarrhea are withdrawal indication, otherwise there will be serious oropharyngeal and intestinal ulcers. Intravenous administration of gastrointestinal toxicity is often limiting dose. On the contrary, huge doses of intravenous injection, white cell reduction is the dose limiting toxicity. Low white cell counts often appear in medication for the first time after 7 to 14 days. Thrombocytopenia is not too obvious, appeared in 7~17. Monitoring of blood cell count is necessary.
Other adverse reactions are hair loss, dermatitis and pigment calm. There were acute and chronic conjunctivitis. Reversible cerebellar ataxia occurs in 1% of patients, possibly is related to the dose, occur at any time of the treatment process (often a few months later). After Cerebellar signs in the withdrawal can be last for a few of weeks. Myocardial ischemia occasionally appeared in the 5-FU intravenous drip. The drug in animals is caused by abnormal and may be carcinogenic.
Damage to the liver function of patients (e.g. extensive liver metastasis) fluorouracil should be reduced; The nutritional status of patients with poor medication should be cautious.
Using daily intermittent intravenous drip for 4~5d, can greatly reduce the toxic effects of blood. However, the results of clinical research mean rapid injection or intravenous drip method in the treatment of superiority. Long term intravenous drip infusion can be accompanied by pain, erythema and skin scaling of hand-foot comprehensive syndrome.
This medicine to FDA pregnancy category D.
[Fluorofur]

Fluorofur is fluorine urea pyrimidine derivatives, and effect is similar with fluorouracil, but chemotherapy index double higher than fluorouracil and toxicity is only the 1/4 to 1/6 of fluorouracil. It is suitable for gastrointestinal cancer and breast cancer. There are oral, intravenous and anal suppository three formulations.
[Chemical property]

It is white or white crystalline powder. Mp is 282-283℃ (decomposition), 0.1 mol/L hydrochloric acid solution has maximum absorption at 265nm wavelength. It is slightly soluble in water and ethanol, insoluble in chloroform and ether, soluble in dilute hydrochloric acid and sodium hydroxide solution. Medium toxicity, LD50 (mouse, i.p.) is 230mg/kg.
[Uses]

1. It is used for biochemical studies and antitumor drugs.
2. It is the anti tumor drug, also used for synthesis of flucytosine. 5-fluorouracil can be used in the study of rice in the biochemical studies, ear differentiation, genetic metabolic measurement, plant growth development research.
3. It is used for the digestive system cancer, head and neck cancer, gynecological cancer, lung cancer, liver cancer, treatment of bladder cancer and skin cancer.
4. Antimetabolite antitumor drugs.
5. Anti tumor drugs. There is a certain effect on a variety of tumors such as digestive tract cancer, breast cancer, ovarian cancer, chorionic epithelial cancer, cervical cancer, hepatocellular carcinoma, bladder cancer, skin cancer (topical), leukoplakia (topical) etc. Adverse reactions mainly are bone marrow transplantation, digestive tract reaction, serious person can have diarrhea, local injection site phlebitis, a few of which have nervous system reactions such as cerebellar degeneration and ataxia. The course of medication should strictly check the blood.
[Methods of production]

1. It is obtained by fluoride ethyl acetate by condensation, cyclization and hydrolysis.
(1). Condensation, cyclization. Sodium methoxide is input dry stainless steel reaction pot, stirring under vacuum concentration to sodium methoxide into white powder, cooling to 50℃, adding toluene, then cold to below 10℃, dropping ethyl formate. After adding remained below 10℃, dripping ethyl fluoroacetate. Completely, at about 30℃ stirring reaction for 8 hours. Static, obtain pale yellow thick mixture. In the condensation product, adding methanol and methyl isobutyl urea sulfate, stirring and heating to 66-70℃, reflux reaction for 6h. Atmospheric recovering methanol to the reaction material showing a thin paste, then vacuum distilled to viscous so far. Heating, dissolving in water, adding activated charcoal, filtered, and the filtrate with concentrated hydrochloric acid to pH3-4, crystallization, cooling and filtering, use cold water to wash the filter cake, using boiling water to regulate plasma immersion to recognize, filtering, water washing, drying, to 5-fluorouracil (-4-hydroxy-2-four oxygen pyrimidine C5H5FN2O2. (2). The hydrolysis of the cyclization product 5-Fluoro-4-hydroxy-2-methoxy pyrimidine and adding 20% hydrochloric acid in 60℃are hydrolysis for 4h, after processing to obtain 5-fluorouracil.
2. 2-methylthio-5-fluorouracil is under acidic conditions and reflux system to obtain 5-fluorouracil.
Spectrum DetailBack Directory
[Spectrum Detail]

5-Fluorouracil(51-21-8)MS
5-Fluorouracil(51-21-8)1HNMR
5-Fluorouracil(51-21-8)IR2
5-Fluorouracil(51-21-8)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

5-Fluorouracil, 99%(51-21-8)
[Alfa Aesar]

5-Fluorouracil, 99%(51-21-8)
[Sigma Aldrich]

51-21-8(sigmaaldrich)
[TCI AMERICA]

5-Fluorouracil,>99.0%(LC)(T)(51-21-8)
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