Fluorouracil

Base Information

• Chemical Name: Fluorouracil
• CAS No.: 51-21-8
• Deprecated CAS: 1004-03-1,4921-97-5,79108-01-3,4921-97-5
• Molecular Formula: C4H3FN2O2
• Molecular Weight: 130.078
• Hs Code.: 2933.59
• European Community (EC) Number: 200-085-6
• NSC Number: 757036,19893
• UNII: U3P01618RT
• DSSTox Substance ID: DTXSID2020634
• Nikkaji Number: J4.489J
• Wikipedia: Fluorouracil
• Wikidata: Q238512
• NCI Thesaurus Code: C505
• RXCUI: 4492
• Pharos Ligand ID: 9H3BPYUFMWX4
• Metabolomics Workbench ID: 42881
• ChEMBL ID: CHEMBL185
• Mol file: 51-21-8.mol

Synonyms:5 Fluorouracil;5 Fluorouracil biosyn;5 FU Lederle;5 FU medac;5 HU Hexal;5-Fluorouracil;5-Fluorouracil-biosyn;5-FU;5-FU Lederle;5-FU medac;5-HU Hexal;5FU;Adrucil;Carac;Dakota, Fluorouracile;Efudex;Efudix;Fluoro Uracile ICN;Fluoro-Uracile ICN;Fluoroplex;Fluorouracil;Fluorouracil GRY;Fluorouracil Mononitrate;Fluorouracil Monopotassium Salt;Fluorouracil Monosodium Salt;Fluorouracil Potassium Salt;Fluorouracil-GRY;Fluorouracile Dakota;Fluorouracilo Ferrer Far;Fluoruracil;Fluracedyl;Flurodex;Haemato fu;Haemato-fu;Neofluor;Onkofluor;Ribofluor

Chemical Property of Fluorouracil

Chemical Property:

• Appearance/Colour: white to nearly white crystalline powder
• Melting Point: 282-286 °C (dec.)(lit.)
• Refractive Index: 1.542
• Boiling Point: 401.4 °C at 760 mmHg
• PKA: pKa 8.0±0.1 (H2O) (Uncertain);3.0±0.1(H2O) (Uncertain)
• Flash Point: 196.5 °C
• PSA: 65.72000
• Density: 1.53 g/cm³
• LogP: -0.79770
• Storage Temp.: Store at 0-5
• Sensitive.: Air Sensitive
• Solubility.: H2O: 10 mg/mL, clear
• Water Solubility.: 12.2 g/L 20 ºC
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.01785550
• Heavy Atom Count: 9
• Complexity: 199

Purity/Quality:

99.0%min ^*data from raw suppliers

5-Fluorouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,C,Xi
• Hazard Codes: Xn,T,C,Xi
• Statements: 22-20/21/22-52-25
• Safety Statements: 36-36/37-36/37/39-22-45-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1=C(C(=O)NC(=O)N1)F
• Recent ClinicalTrials: Combination Chemotherapy and Bevacizumab in Treating Patients With Advanced Neuroendocrine Tumors
• Recent EU Clinical Trials: The PRESTO Trial-
• Recent NIPH Clinical Trials: Multicenter Phase II Study of AHCC (Functional Food) to Explore Improvement in Treatment Outcome in Patients with Unresectable Pancreatic Cancer
• 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. Fluorouracil (5-fluorouracil, 5-fluorouracil, Efudex, Adrucil) is a halogenated pyrimidine analogue that must be activated metabolically. The active metabolite that inhibits DNA synthesis is the deoxyribonucleotide 5-fluoro-2'deoxyuridine-S'-phosphate (FdUMP). 5- Fluorouracil is selectively toxic to proliferating rather than non-proliferating cells and is active in both the G1- and S-phases. The target enzyme inhibited by 5-fluorouracilfluorouracil is thymidylate synthetase. methylenetetrahydrofolate dihydrofolate The carbon-donating cofactor for this reaction is N5,N10 methylenetetrahydrofolate, which is converted to dihydrofolate. The reduced folate cofactor occupies an allosteric site on thymidylate synthetase, which allows for the covalent binding of 5-FdUMP to the active site of the enzyme.
• 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. 5-Fluorouracil is used as an antitumor agent in the treatment of anal, breast, colorectal, oesophageal, stomach, pancreatic and skin cancers. It finds application as a suicide inhibitor due to its irreversible inhibition of thymidylate synthase. It is also used in the treatment of actinic keratoses and bowen's disease. Further, it serves as a potent antineoplastic agent in clinical use. In addition to this, it acts as a DNA synthesis inhibitor. antineoplastic, pyrimidine antimetabolite 5-Fluoro Uracil is an active metabolite of Doxifluridine (D556750). A potent antineoplastic agent in clinical use. Also an inhibitor of DNA synthesis
• Description: 5-Fluorouracil (5-FU) is a prodrug form of the thymidylate synthase inhibitor fluorodeoxyuridylate (FdUMP). It is also converted to the active metabolites FUTP and FdUTP, which induce RNA and DNA damage, respectively. In vivo, 5-FU (15 mg/kg) when administered in combination with docetaxel reduces tumor growth in B88 and CAL 27 oral squamous cell carcinoma (OSCC) mouse xenograft models. Formulations containing 5-FU have been used in the treatment of colorectal, breast, gastric, and pancreatic cancers.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: 5-Fluorouracil (Efudex, Fluoroplex) is an antimetabolite used for the topical treatment of actinic keratoses. It is also useful for the treatment of superficial basal cell carcinomas when conventional surgical modalities are impractical. 5-Fluorouracil (FU) is widely used in the treatment of a range of cancers including breast and cancers of the aerodigestive tract, but has had the greatest impact in colorectal cancer. 5-FU-based chemotherapy improves overall and disease-free survival of patients with resected stage III colorectal cancer. Nonetheless, response rates for 5-FU-based chemotherapy as a first-line treatment for advanced colorectal cancer are only between 10 and 15%. Combination of 5-FU with newer chemotherapies, such as irinotecan and oxaliplatin, has improved the response rates for advanced colorectal cancer to between 40 and 50%. 5-Fluorouracil is used in several combination regimens in the treatment of breast cancer. It also has palliative activity in gastrointestinal adenocarcinomas, including those originating in the stomach, pancreas, liver, colon, and rectum. Other tumors in which some antitumor effects have been reported include carcinomas of the ovary, cervix, oropharynx, bladder, and prostate. Topical 5-fluorouracil cream has been useful in the treatment of premalignant keratoses of the skin and superficial basal cell carcinomas, but it should not be used in invasive skin cancer.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhances effect of coumarins. Antipsychotics: avoid concomitant use with clozapine, increased risk of agranulocytosis. Cytotoxics: avoid with panitumumab. Folic acid: toxicity of fluorouracil increased - avoid. Metronidazole and cimetidine inhibit metabolism (increased toxicity). Temoporfin: increased skin photosensitivity with topical fluorouracil

Technology Process of Fluorouracil

There total 143 articles about Fluorouracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil → 5-fluorouracil (51-21-8)

Guidance literature:

With sulfuric acid; In water; at 80 ℃; for 7h;

DOI:10.1007/s10593-015-1737-y

Reference yield: 93.0%

2,5-difluoro-4-chloro-pyrimidine (99429-06-8) → 5-fluorouracil (51-21-8)

Guidance literature:

With sodium hydroxide; In water; at 80 ℃; for 4h;

DOI:10.1016/S0022-1139(00)82875-4

Reference yield: 90.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-fluorouracil (51-21-8)

Guidance literature:

With C₁₉XeF₆; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(00)71188-9

upstream raw materials:

5-fluoro-2-thiouracil

5-fluoro-2-methylthio-3H-pyrimidin-4-one

2-ethylthio-5-fluoro-4(1H)-pyrimidinone

5-fluoroorotic acid

Downstream raw materials:

1-methylcarbonyl-5-fluorouracil

1,3-Di(piperidylmethyl)-5-fluoruracil

1-Methyl-5-fluor-uracil

3-(o-nitrobenzyloxycarbonyl)-5-fluorouracil

Refernces

• 1、 Zhang, Zhongshan,Zhang, Quanbin,Wang, Jing,Shi, Xuelian,Zhang, Jingjing,Song, Houfang. "Synthesis and drug release in vitro of porphyran carrying 5-Fluorouracil". . p. 628 - 632. Retrieved 2010.
• 2、 Lal,Pastore,Pesaresi. "A convenient synthesis of 5-fluoropyrimidines using 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate)-SELECTFLUOR reagent". . p. 7340 - 7342. Retrieved 1995.
• 3、 Kawase,Samejima,Okada,Ochi,Matsunaga. "Syntheses and biological activities of N1-(2-formylethyl)-5-fluorouracil and related compounds". . p. 2395 - 2402. Retrieved 1985.
• 4、 Chernikova, Inna B.,Khursan, Sergey L.,Spirikhin, Leonid V.,Yunusov, Marat S.. "5-fluoro-5-halo- and 5-fluoro-5-nitro-substituted uracil derivatives. synthesis and structure". . p. 568 - 572. Retrieved 2015.
• 5、 Maurin'sh, Yu. A.,Paegle, R. A.,Khagi, Kh. V.,Meirena, D. V.,Simkhovich, B. Z.,Lidak, M. Yu.. "1-(5-FLUOROURACIL-1-YL)-2,5-DI-O-ACETYL-β-D-GLUCOFURANURONO-6,3-LACTONE, A NEW TRANSPORT FORM OF 5-FLUOROURACIL". . p. 466 - 469. Retrieved 1988.
• 6、 Hamada,Fukushima,Saneyoshi,Kawaguchi,Nakano. "Inhibition of 5'-deoxy-5-flourouridine phospholysis by acyclopyrimidinenucleosides in intestinal tissue homogenates". . p. 172 - 175. Retrieved 1995.
• 7、 Reyes, Archie C.,Amyes, Tina L.,Richard, John P.. "Enzyme Architecture: Erection of Active Orotidine 5′-Monophosphate Decarboxylase by Substrate-Induced Conformational Changes". . p. 16048 - 16051. Retrieved 2017.
• 8、 Barton et al.. "-". . p. 329. Retrieved 1972.
• 9、 Anbar,Neta. "-". . p. 2757,2760. Retrieved 1962.
• 10、 -. "Green preparation process for preparing 5-fluorouracil". Paragraph 0012-0015. . Retrieved 2021/07/17.