5-Fluorouracil
5-Fluorouracil
CAS: 51-21-8
Molecular Formula: C4H3FN2O2
5-Fluorouracil - Names and Identifiers
| Name | 5-Fluorouracil |
| Synonyms | 5-faracil Fluoracil Tegadifure Fluoroplex 5-Flouracyl Fluorouracil 5-Fluorouracil fluoro-uracile Fluorouracilum 5-fluoro uracil Fluorouracil, 5- [180]-5-Fluorouracil 5-fluoro-2,4-pyrimidinedione 5-fluoropyrimidine-2,4-dione 2,4-dioxo-5-fluoropyrimidine 3h)-pyrimidinedione,5-fluoro-4(1h 5-Fluoro-2,4-(1H,3H)-pyrimidindion 1-fluoropyrimidine-2,4(1H,3H)-dione 5-Fluoro-2,4(1H,3H)-pyrimidinedione 2,4(1H,3H)-Pyrimidinedione, 5-fluoro- |
| CAS | 51-21-8 |
| EINECS | 200-085-6 |
| InChI | InChI=1/C4H3FN2O2/c5-7-2-1-3(8)6-4(7)9/h1-2H,(H,6,8,9) |
| InChIKey | GHASVSINZRGABV-UHFFFAOYSA-N |
5-Fluorouracil - Physico-chemical Properties
| Molecular Formula | C4H3FN2O2 |
| Molar Mass | 130.08 |
| Density | 1.4593 (estimate) |
| Melting Point | 282-286 °C (dec.) (lit.) |
| Boling Point | 190-200°C/0.1mmHg |
| Water Solubility | 12.2 g/L 20 ºC |
| Solubility | Slightly soluble in ethanol. It is almost insoluble in chloroform and dissolved in sodium hydroxide solution. |
| Appearance | White or white-like crystalline powder |
| Color | white |
| Merck | 14,4181 |
| BRN | 127172 |
| pKa | pKa 8.0±0.1 (H2O) (Uncertain);3.0±0.1(H2O) (Uncertain) |
| PH | 4.3-5.3 (10g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Light sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases. |
| Sensitive | Air Sensitive |
| Refractive Index | 1.542 |
| MDL | MFCD00006018 |
| Physical and Chemical Properties | melting point 282-286°C (dec.)(lit.) |
| Use | For digestive system cancer, head and neck cancer, gynecological cancer, lung cancer, liver cancer, bladder cancer and skin cancer treatment |
5-Fluorouracil - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R52 - Harmful to aquatic organisms R25 - Toxic if swallowed |
| Safety Description | 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. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | YR0350000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | T |
| HS Code | 29335995 |
| Hazard Note | Irritant/Highly Toxic |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 230 mg/kg |
5-Fluorouracil - Reference
| Reference Show more | 1. Xie, Hao, Gui, Wei, Ming, Chen, Mei, Zhen, et al. Synergistic Anti-tumor effect of three polysaccharides in vitro [J]. Food Science 2013(15):289-294. 2. Wan Yongxing, Zhu, Jin Li, Sun Tongming, et al. Synthesis and photo-control properties of 4-(5 '-fluorouracil methyl)-3-nitrobenzoic acid [J]. Chemical reagents 2019(11). 3. Zhang Lujie, Guo Yibing, Shi Lu, et al. Release behavior of 5-fluorouracil from P (γ-pga-co-nipaam) hydrogel [J]. Journal of Functional Polymers, 2015(01):91-96. 4. Zhong Sien, Liu, Yang, Cao, Chie et al. Inhibitory effects of three polysaccharide degradation complexes on proliferation of HeLa cells in vitro [J]. Modern food science and technology 2018 034(010):72-80 7. 5. Ruan Shanming, Shen Min, He Wang, Yi Lin Hong, Zheng Liping, Li monting, Zhang Kai. Effect of optimized intervention of traditional Chinese medicine detoxification method on overall survival time and expression of Caspase-3, ROCK2 and mTOR in BALB/c colon cancer mice [J]. Chinese Journal of Traditional Chinese Medicine, 2013, 28(06):1714-1718. 6. Ruan Shanming, Shen Min, He Wang, Yi Lin Hong, Zheng Liping, Li monting, Zhang Kai. Experimental study on optimal intervention of Chinese Medicine detoxification method on CEA and sCD44 in BALB/c colon cancer mice [J]. World Traditional Chinese Medicine 2013 8(03):313-317. 7. Xie Fei, Cao, pure Chen, Meizhen et al. Optimization of protein removal process and antioxidant activity of Porphyra haitanensis polysaccharide by response surface methodology [J]. Food science 2016 37(22):77-84. 8. Ju Yaoyao, Cao, pure Chen, Meizhen, Ye, Astronomy. Optimization of extraction process of polysaccharide from Crispus and its inhibitory effect on tumor cells by response surface methodology [J]. Food Science, 2016, 37(08):57-62. 9. Wu cast, Yang Ruiqi, Chen Meizhen, etc. Antitumor effect of conjugated products of linoleic acid from Salicornia seed oil [J]. Food Science, 2012, 033(023):318-322. 10. Ju Yaoyao, Ye astronomy, Xie Fei, et al. Anti-tumor activity and mechanism of polysaccharide from Crispus Crispus in vivo [J]. Food Science, 2016, 037(005):208-213. 11. Zhang Tingting, Zhou Zhuoyan, Li Junfeng, etc. Effect of Jiedu quyu Ziyin decoction on tumor growth and immune function in H22 tumor-bearing mice [J]. Zhejiang Journal of Traditional Chinese Medicine, 2019, 54(03):176-177. 12. He Baoyuan, Zhang Baoyan, Li Shan, Xue Haiyan. Preparation and drug release properties of 5-fluorouracil loaded chitosan/gelatin microparticles [J]. Chemical Progress (Phase 7):2151-2155. 13. Xie Fei, Li Wei, Chen Meizhen, et al. Antitumor activity and mechanism of polysaccharides from wild cicada [J]. Food Science, 2016, 37(13):209-213. 14. Liu Wen-jing, Yang Wen, Liu Fei, et al. Preliminary Study on anti-tumor active substances in rats [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2017, 10(v.19;No.162):17-20. 15. In summer, Han Haixia, Feng Wei, Fang Lijun, Fu Xia. Therapeutic effect and mechanism of polyphylla saponin VII on pancreatic cancer in nude mice [J]. Journal of Guangzhou University of Traditional Chinese Medicine, 2021,38(04):785-790. 16. Zhang, Huidan, et al. "Heavy ion mutagenesis combined with triclosan screening provides a new strategy for improving the arachidonic acid yield in mortierella alpina." BMC biotechnology 18.1 (2018): 1-9. 17. Gao, Xiaoxu, et al. "Comparative analysis of chemical composition, anti-inflammatory activity and antitumor activity in essential oils from Siegesbeckia orientalis, S. glabrescens and S. pubescens with an ITS sequence analysis." Molecules 23.9 (2018): 2185 18. Ni, Wenfeng, et al. "Dual-targeting nanoparticles: codelivery of curcumin and 5-fluorouracil for synergistic treatment of hepatocarcinoma ." Journal of pharmaceutical sciences 108.3 (2019): 1284-1295.https://doi.org/10.1016/j.xphs.2018.10.042 19. [IF=6.304] Jiang Ying et al."Furanodienone induces G0/G1 arrest and causes apoptosis via the ROS/MAPKs-mediated caspase-dependent pathway in human colorectal cancer cells: a study in vitro and in vivo."Cell Death Dis. 2017 May;8(5):e2815-e2815 20. [IF=4.411] Xiaoxu Gao et al."Comparative Analysis of Chemical Composition Anti-Inflammatory Activity and Antitumor Activity in Essential Oils from Siegesbeckia orientalis, S. glabrescens and S. pubescens with an ITS Sequence Analysis."Molecules. 2018 Sep;23(9):2185 21. [IF=3.534] Wenfeng Ni et al."Dual-Targeting Nanoparticles: Codelivery of Curcumin and 5-Fluorouracil for Synergistic Treatment of Hepatocarcinoma."J Pharm Sci-Us. 2019 Mar;108:1284 22. [IF=2.563] Zhang Huidan et al."Heavy ion mutagenesis combined with triclosan screening provides a new strategy for improving the arachidonic acid yield in Mortierella alpina."Bmc Biotechnol. 2018 Dec;18(1):1-9 23. [IF=6.331] Zhi Liao et al."Hydroxychloroquine based chemical drug for combination therapy with 5-Fu for inhibiting the pathway of Akt/mTOR in autophagy process on colon cancer."J Mater Chem B. 2021 May;: 24. [IF=5.81] Huixia Feng et al."Exploring Multifunctional Bioactive Components from Podophyllum sinense Using Multi-Target Ultrafiltration."Front Pharmacol. 2021; 12: 749189 25. [IF=4.076] Xinyuan Wang et al."Novel Formulations of the Antiviral Drug Favipiravir: Improving Permeability and Tabletability."Cryst Growth Des. 2021;21(7):3807-3817 26. [IF=3.565] Bolin Yang et al."Inhibiting EMT, stemness and cell cycle involved in baicalin-induced growth inhibition and apoptosis in colorectal cancer cells."J Cancer. 2020; 11(8): 2303-2317 27. [IF=3.565] Liqiang Qian et al."Anti-tumor Activity of Bufalin by Inhibiting c-MET Mediated MEK/ERK and PI3K/AKT Signaling Pathways in Gallbladder Cancer."J Cancer. 2020; 11(11): 3114-3123 28. [IF=2.898] Zhe Deng et al."Synergistic anti-liver cancer effects of curcumin and total ginsenosides."World J Gastro Oncol. 2020 Oct 15; 12(10): 1091-1103 29. [IF=1.679] Zhong-Bo Zhou et al."Two new polycyclic polyprenylated acylphloroglucinols from Hypericum curvisepalum N. Robson."Phytochem Lett. 2022 Apr;48:43 30. [IF=7.376] Chengtao Sun et al."Dihydrotanshinone I inhibits ovarian tumor growth by activating oxidative stress through Keap1-mediated Nrf2 ubiquitination degradation."Free Radical Bio Med. 2022 Feb;180:220 |
5-Fluorouracil - Nature
Open Data Verified Data
- This product is white or off-white crystalline or crystalline powder. Slightly soluble in water, slightly soluble in ethanol, almost insoluble in chloroform; Dissolved in dilute hydrochloric acid or sodium hydroxide solution. Melting point 281~284 °c (decomposition).
- This product is the most commonly used uracil antimetabolite, in the body first through a series of reactions into fluorouracil deoxynucleotide, and then play an effect (affect DNA synthesis); it can also be converted into fluorouracil nucleoside in vivo and incorporated into RNA, thus interfering with protein synthesis. The main effect is in the S phase, but it also has a certain effect on other cells. Easy to penetrate the blood-brain barrier, easy to enter the brain tissue and tumor metastases. About 10% to 30% of the prototype is excreted in the urine, and about 60% to 80% is inactivated in the liver into CO2 and urea, which are excreted by the respiratory tract and urine respectively. This product has a wide anti-tumor spectrum.
Last Update：2024-01-02 23:10:35
5-Fluorouracil - Standard
Authoritative Data Verified Data
This product is 5-fluoro-2, 4 (1H,3H)-pyrimidinedione. The content of C4H3FN202 shall be between 97.0% and 103.0% based on the dry product.
Last Update：2024-01-02 23:10:35
5-Fluorouracil - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline or crystalline powder.
- This product is slightly soluble in water, slightly soluble in ethanol, almost insoluble in chloroform; Dissolved in dilute hydrochloric acid or sodium hydroxide solution.
absorption coefficient
take this product, precision weighing, plus O. 1 mol/L hydrochloric acid solution is dissolved and quantitatively diluted to prepare a solution containing about 12ug per 1 ml, and the absorbance is measured at the wavelength of 265nm by ultraviolet-visible spectrophotometry (General rule 0401), the absorption coefficient is 535 to 568.
Last Update：2022-01-01 13:40:35
5-Fluorouracil - Introduction
This product is first converted into 5-fluoro-2-deoxyuracil nucleotides in the body, which inhibits thymine nucleotide synthase and blocks the conversion of deoxyuracil nucleotides into deoxythymine nucleotides, thereby inhibiting DNA biosynthesis. In addition, by preventing the incorporation of uracil and rotic acid into RNA, the effect of inhibiting RNA synthesis is achieved. This product is a cell cycle specific drug, mainly inhibiting S phase cells.
Last Update：2022-10-16 17:25:40
5-Fluorouracil - Application
Open Data Verified Data
- anticancer drug. Suitable for the treatment of gastric cancer, rectal cancer, breast cancer, ovarian cancer, liver cancer.
- usage and dosage of 150 ~ 200mg each time, 3~4 times a day, a total of 20~30g.
Last Update：2025-08-19 16:24:40
5-Fluorouracil - Differential diagnosis
Authoritative Data Verified Data
- take 5ml of the aqueous solution (1-100) of this product, add 1 ml of bromine test solution, shake, the color of bromine solution will disappear; Add 2ml of barium hydroxide test solution, generate purple precipitate.
- take about 1 ml of saturated sulfuric acid solution of chromium trioxide, put it in a small test tube, turn the test tube, the solution should be evenly coated on the pipe wall; Add about 2mg of fine powder of this product, Micro heat, turn the test tube, the solution should not be evenly applied to the pipe wall, and similar oil scale exists in the pipe wall.
- take the test solution under the content determination item and measure it by ultraviolet-visible spectrophotometry (General rule 0401), which has the maximum absorption at the wavelength of 265nm, there is minimal absorption at a wavelength of 232nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 280).
Last Update：2022-01-01 13:40:36
5-Fluorouracil - Safety
Open Data Verified Data
The toxicity was less than that of fuflurouracil and myelosuppression was slight. A decrease in the number of white blood cells may occur when the amount is large. The more common adverse reactions are gastrointestinal reactions, such as Nausea, Vomit, generally not serious. If the reaction is strong, can be reduced or suspended after a few days. Liver and kidney dysfunction should be used with caution and close observation.
Last Update：2022-01-01 11:12:33
5-Fluorouracil - Exam
Authoritative Data Verified Data
fluorine content
take this product about 15mg, precision weighing, according to the fluorine inspection method (General 0805) determination, fluorine content should be 13.1% ~ 14.6%.
clarity of the solution
take 0.10g of this product, Add 10ml of water to dissolve, the solution should be clear; If it is turbid, compared with No. 1 turbidity standard solution (General rule 0902 first method), it should not be more concentrated.
chloride
take 2.0g of this product, add 100ml of water, heat to dissolve, cool, filter; Take the filtrate 25ml, check according to law (General rule 0801), and standard sodium chloride solution 7.0ml of the control solution should not be more concentrated (0.014%).
sulfate
take 50ml of the filtrate remaining under the above chloride item and check it according to law (General 0802). Compared with the control solution made of 2.0ml of standard potassium sulfate solution, it should not be more concentrated (0.02%).
Related substances
take this product, add mobile phase to dissolve and dilute to make about O in each lml. A 1 mg solution was used as a test solution; An appropriate amount was quantitatively diluted with a mobile phase to prepare a solution containing about 0.25ug per 1 ml as a control solution. Test according to high performance liquid chromatography (General 0512). Silica gel was bonded with eighteen alkyl silane as filler, and water (adjusted to pH 0.05 with 3.5 mol/L phosphoric acid solution)-methanol (95:5) as mobile phase, and the detection wavelength was 265nm. The number of theoretical plates shall not be less than 2500 calculated by the fluorouracil peak, and the separation degree between the fluorouracil peak and the adjacent impurity peak shall meet the requirements. 20ul of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 5 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be more than 2 times (0.5%) the area of the main peak of the control solution, the sum of each impurity peak area shall not be greater than 3 times (0.75%) of the main peak area of the control solution.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
Heavy metals
take 0.50g of this product, inspection according to law (General rule 0821 third law), containing heavy metals shall not exceed 20 parts per million.
Last Update：2022-01-01 13:40:37
5-Fluorouracil - Content determination
Authoritative Data Verified Data
take this product, precision weighing, add 0.1 mol/L hydrochloric acid solution is dissolved and quantitatively diluted to prepare a solution containing about lOug per 1 ml, which is used as a test solution according to ultraviolet-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 265nm, and the absorption coefficient of C4H3FN202 was calculated as 552.
Last Update：2022-01-01 13:40:38
5-Fluorouracil - Category
Authoritative Data Verified Data
antineoplastic agents.
Last Update：2022-01-01 13:40:38
5-Fluorouracil - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 13:40:38
5-Fluorouracil - Fluorouracil cream
Authoritative Data Verified Data
This product contains fluorouracil (C4H3FN202) should be labeled the amount of 90.0% ~ 110.0%.
trait
This product is white cream.
identification
Take lg of this product, add 35ml of water, heat it on a water bath to melt it, cool it in an ice bath, filter it, evaporate the filtrate to dryness, and identify the residue under fluorouracil (1), (2) the test showed the same response.
examination
should comply with the relevant provisions under Cream (General rule 0109).
Content determination
take an appropriate amount of this product (approximately equivalent to fluorouracil O.lg), Precision weighing, adding lg of sodium chloride, heating and melting on a water bath, adding 50ml of water, boiling, dissolving fluorouracil, allowing to cool, filtering, placing the filtrate in a 200nd measuring flask, extract three times with the same method, wash the filter with water, wash the liquid and the measuring flask, dilute to the scale with water, shake well, take with precision, and measure according to the nitrogen determination method (General rule 0704 method 1). Each 1 ml of sulfuric acid titration solution (0.05mol/L) is equivalent to 6.504mg of C4H3FN202.
category
with fluorouracil.
specification
(l)4g:20mg (2)4g:lOOmg
storage
sealed and stored in a cool place.
Last Update：2022-01-01 13:40:39
5-Fluorouracil - Fluorouracil injection
Authoritative Data Verified Data
This product is a sterilized aqueous solution prepared by adding appropriate amount of sodium hydroxide to fluorouracil. The content of Fluorouracil (C4H3FN202) shall be between 93.0% and 107.0% of the labeled amount.
trait
This product is colorless or almost colorless clear liquid.
identification
- take 2ml of this product, add 1ml of bromine test solution, shake, the color of bromine solution will disappear; Add 2ml of barium hydroxide test solution, generate purple precipitate.
- take about 1ml of saturated sulfuric acid solution of chromium trioxide, put it in a small test tube, turn the test tube, the solution should be evenly coated on the tube wall; Add 2 drops of this product, slightly heat, turn the test tube, the solution should not be evenly applied to the pipe wall, and similar oil scale exists in the pipe wall.
- take the test solution under the content determination item and measure it by ultraviolet-visible spectrophotometry (General rule 0401), which has the maximum absorption at the wavelength of 265nm, there is minimal absorption at a wavelength of 232nm.
examination
- the pH value should be 8.4 to 9.2 (General 0631).
- Related substances take appropriate amount of this product and dilute it with mobile phase to prepare about 0. 5% fluorouracil per 1 ml. A 1 mg solution was used as a test solution; An appropriate amount was quantitatively diluted with a mobile phase to prepare a solution containing about 0.25ug of fluorouracil per 1 ml as a control solution. Determination according to the method of fluorouracil related substances. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be more than 2 times (0.5%) the area of the main peak of the control solution, the sum of each impurity peak area shall not be greater than 3 times the main peak area of the control solution (O.75%).
- the bacterial endotoxin of this product is taken and checked according to law (General rule 1143). The amount of endotoxin in fluorouracil per 1 mg should be less than 0.25EU.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
precision take the right amount of this product, with O. 1 mol/L hydrochloric acid solution is quantitatively diluted to prepare a solution containing 10ug of fluorouracil per 1 ml, which is used as the test solution according to ultraviolet-visible spectrophotometry (General rule 0401), the absorbance was measured at a wavelength of 265mn, and calculated as the absorption coefficient of C4H3FN202 was 552.
category
with fluorouracil.
specification
(l)5ml:0.125g (2)l0ml:0.25g
storage
light shielding, closed storage.
Last Update：2022-01-01 13:40:40
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View History
5-Fluorouracil
Antioxidant 1010
2079-00-7
Phenyl propargyl ether
6949-98-0
POLYURETHANEOLIGOMERS
4187-53-5
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Antioxidant 1010
2079-00-7
Phenyl propargyl ether
6949-98-0
POLYURETHANEOLIGOMERS
4187-53-5
6027-02-7
Adriblastin
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