Description

Fluorouracil (CAS 51-21-8) is a fluorinated pyrimidine analog with the molecular formula C₄H₃FN₂O₂ and IUPAC name 5-fluoro-1H-pyrimidine-2,4-dione. This antimetabolite and antineoplastic agent is widely utilized in oncology research and clinical applications due to its ability to inhibit thymidylate synthase, disrupting DNA and RNA synthesis. Fluorouracil is supplied as a high-purity white crystalline powder, ensuring consistency for laboratory and pharmaceutical use. It is soluble in water, dimethyl sulfoxide (DMSO), and alkaline solutions, making it suitable for in vitro and in vivo studies. Store at 2-8°C in a tightly sealed container to maintain stability. Suitable for research in cancer therapeutics, cell biology, and molecular pharmacology.

Properties

• CAS Number: 51-21-8
• Complexity: 199
• IUPAC Name: 5-fluoro-1H-pyrimidine-2,4-dione
• InChI: InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChI Key: GHASVSINZRGABV-UHFFFAOYSA-N
• Exact Mass: 130.01785550
• Molecular Formula: C4H3FN2O2
• Molecular Weight: 130.08
• SMILES: C1=C(C(=O)NC(=O)N1)F
• Topological: 58.2
• Monoisotopic Mass: 130.01785550
• Physical Description: Fluorouracil is a white to nearly white crystalline powder; practically odorless. Used as an anti neoplastic drug, chemosterilant for insects.
• Color/Form: White to practically white crystalline powder
• Odor: PRACTICALLY ODORLESS
• Boiling Point: Decomposes at 282-283 °C; sublimes : 190-200 °C
• Melting Point: Decomposes at 540-541 °F
• Solubility: less than 1 mg/mL at 66 °F
• Stability/Shelf Life: Stable when exposed to air.
• Dissociation Constants: 8.02
• Synonyms: 5-Fluorouracil, fluorouracil, 5-FU, Fluracil, Fluoroblastin, Queroplex, 5-fluoropyrimidine-2,4(1H,3H)-dione, Phthoruracil, Carzonal, Kecimeton, Fluril, Fluracilum, Ulup, 5-Fluoracil, Fluorouracilum, Fluro Uracil, 5 Fluorouracil, 5-Fluoruracil, Fluorouracilo, Ftoruracil, Fluri, 5-Fluoro-2,4(1H,3H)-pyrimidinedione, Effluderm (free base), Fluroblastin, 5-Fluoropyrimidine-2,4-dione, Fluoro-uracile, Fluoro-uracilo, Uracil, 5-fluoro-, Ro 2-9757, 5-Faracil, Cinco FU, Fluorouracile, 5-fluoro-uracil, 5-Fluor-2,4-pyrimidindiol, 2,4-Dioxo-5-fluoropyrimidine, Fluorouricil, NSC-19893, 5-Fluoropyrimidin-2,4-diol, 5-Fluoro-2,4-pyrimidinedione, NSC 19893, Fluorouracil Cream, 5-Fluor-2,4-dihydroxypyrimidin, Ro-2-9757, U-8953, Fluorouracilum [INN-Latin], Fluorouracilo [INN-Spanish], Fluouracil, CCRIS 2582, Fluoro Uracil, HSDB 3228, 5-Fluracil, EINECS 200-085-6, FU, 5-Fluor-2,4(1H,3H)-pyrimidindion, UNII-U3P01618RT, 5 FU, DTXSID2020634, CHEBI:46345, AI3-25297, U3P01618RT, NSC19893, Ro-29757, 5FU, DTXCID40634, EC 200-085-6, Fluorouracil [USAN:USP:INN:BAN:JAN], Fluorouracilum (INN-Latin), Fluorouracilo (INN-Spanish), FLUOROURACIL (MART.), FLUOROURACIL [MART.], FLUOROURACIL (USP-RS), FLUOROURACIL [USP-RS], 5-FLUOROURACIL (IARC), 5-FLUOROURACIL [IARC], Flurablastin, FLUOROURACIL (EP MONOGRAPH), FLUOROURACIL [EP MONOGRAPH], FLUOROURACIL (USP MONOGRAPH), FLUOROURACIL [USP MONOGRAPH], Fluorouracil (USAN:USP:INN:BAN:JAN), FLUCYTOSINE IMPURITY A (EP IMPURITY), FLUCYTOSINE IMPURITY A [EP IMPURITY], AccuSite, 5 Fluorouracilum, FLUCYTOSINE IMPURITY A, EMTRICITABINE IMPURITY F, L01BC02, 5-Fluoro-2,4(1H, 3H)-pyrimidinedione, 5-Fluoropyrimidine-2,4-(1H,3H)-dione, 5-FLUOROPYRIMIDIN-2,4(1H,3H)-DIONE, 200-085-6, 51-21-8, Fluoroplex, Efudex, Adrucil, Carac, Timazin, Arumel, Efudix, 5-fluoro-1H-pyrimidine-2,4-dione, Efurix, 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-, 2,4-Dihydroxy-5-fluoropyrimidine, 5-fluoropyrimidine-2,4-diol, 5-fluoro uracil, 5-Ftouracyl, Fluorouracil, 5-, Tolak, 191047-65-1, 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione, MFCD00006018, CHEMBL185, 2,4-Pyrimidinediol, 5-fluoro- (9CI), MLS000069498, 191047-64-0, 191115-88-5, Phtoruracil, URF, NCGC00015442-02, Effluderm, SMR000038082, Fluorouracile [DCIT], 5-Fluoracil [German], 5-Fluoracyl, 5-Fluoruracil [German], 1004-03-1, CAS-51-21-8, Fluoroplex (TN), 5-Fluor-2,4-pyrimidindiol [Czech], Adrucil (TN), 5-fluoro-1,3-dihydropyrimidine-2,4-dione, Carac (TN), 5-Fluor-2,4-dihydroxypyrimidin [Czech], SR-01000075881, 5-Fluor-2,4(1H,3H)-pyrimidindion [Czech], inhibits thymilidate synthetase, 2,4-Dioxo-5-fluoropryimidine, 5-fluorourasil, 5-florouracil, 5-fluorouacil, 5-FU (TN), 1upf, 5F-uracil, U 8953, Fluorouracil; 5-Fluoropyrimidine-2,4(1H,3H)-dione; Flucytosine Imp. A (EP); Flucytosine Impurity A, Adrucil (ICN), 2794-13-0, Adrucil (Fluorouracil), Spectrum_000841, Opera_ID_134, 5-Fluorouracil, 99%, Spectrum2_000076, Spectrum3_000434, Spectrum4_000557, Spectrum5_000718, WLN: T6MVMVJ EF, FLUOROURACIL [MI], Lopac-F-6627, F0151, 5-Fluorouracil (5-FU), FLUOROURACIL [INN], FLUOROURACIL [JAN], 5-Fluorouracil (Standard), UPCMLD-DP130, F 6627, FLUOROURACIL [HSDB], FLUOROURACIL [USAN], SCHEMBL3646, 5-fluorpyrimidin-2,4-diol, FLUOROURACIL [VANDF], Folfox component fluorouracil, Lopac0_000536, BSPBio_002048, KBioGR_001253, KBioSS_001321, 2(1H)-Pyrimidinone, 5-fluoro-4-hydroxy- (9CI), 4(3H)-Pyrimidinone, 5-fluoro-2-hydroxy- (9CI), MLS002415705, DivK1c_000054, FLUOROURACIL [WHO-DD], FLUOROURACIL [WHO-IP], SCHEMBL592897, SPECTRUM1500305, SPBio_000291, 5-fluoro-2,4-dioxo-pyrimidin, 5-fluoro-pyrimidine-2,4-diol, GTPL4789, SCHEMBL2733944, SCHEMBL8012255, SCHEMBL10746579, UPCMLD-DP130:001, Fluorouracil (JP18/USP/INN), HMS500C16, KBio1_000054, KBio2_001321, KBio2_003889, KBio2_006457, KBio3_001268, 5-Fluoro-2,3H)-pyrimidinedione, 5-FLUOROURACIL [WHO-IP], 2,4-Pyrimidinedione, 5-fluoro-, NINDS_000054, BCPP000428, FLUOROURACIL [ORANGE BOOK], HMS1920O18, HMS2090I04, HMS2091F19, HMS3259O03, HMS3261L13, HMS3654K22, HMS3715H03, HMS3865L03, HMS5079C17, Pharmakon1600-01500305, 5-Fluorouracil, analytical standard, BCP02083, MSK10715, TCA94195, 2,3H)-Pyrimidinedione, 5-fluoro-, 5-Fluorouracil – Bio-X trade mark, Fluorouracil (5-Fluoracil, 5-FU), Fluorouracil (5-Fluoracil; 5-FU), Tox21_110150, Tox21_202335, Tox21_300112, Tox21_500536, BDBM50340677, CCG-39879, DL-399, HY-90006R, NSC757036, NSC816997, s1209, SBB085751, STK297802, STL367375, FLUOROURACILUM [WHO-IP LATIN], AKOS000119162, AKOS003237897, AKOS008044307, Tox21_110150_1, BCP9000239, CS-0993, DB00544, FF05372, KS-5129, LP00536, NC00454, NSC-757036, NSC-816997, SDCCGSBI-0050519.P005, FLUCYTOSINE IMPURITY A [WHO-IP], IDI1_000054, NCGC00015442-01, NCGC00015442-03, NCGC00015442-04, NCGC00015442-05, NCGC00015442-06, NCGC00015442-07, NCGC00015442-08, NCGC00015442-09, NCGC00015442-10, NCGC00015442-11, NCGC00015442-12, NCGC00015442-15, NCGC00015442-16, NCGC00015442-24, NCGC00015442-30, NCGC00091349-01, NCGC00091349-02, NCGC00091349-03, NCGC00091349-04, NCGC00091349-05, NCGC00091349-07, NCGC00091349-08, NCGC00254023-01, NCGC00259884-01, NCGC00261221-01, AC-11201, BF166014, EMTRICITABINE IMPURITY F [WHO-IP], HY-90006, NCI60_001652, SRI-10792-04, SRI-10792-05, SRI-10792-06, SRI-10792_07, SRI-10792_08, 5-Fluoro-1H-pyrimidine-2,4-dione(5FU), 5-Fluorouracil, >=99% (HPLC), powder, SBI-0050519.P004, 2(1H)-Pyrimidinone, 5-fluoro-4-hydroxy-, 4(3H)-Pyrimidinone, 5-fluoro-2-hydroxy-, 5-Fluoro-1H-pyrimidine-2,4-dione(5-FU), DB-051923, DB-065735, DB-268958, DB-272209, DB-297613, pyrimidine-2,4(1H,3H)-dione, 5-fluoro-, 5-Fluoro-1H-pyrimidine-2,4-dione (5-FU), EU-0100536, NS00000337, ST45025877, SW199617-3, 5-Fluoro-1H-pyrimidine-2,4-dione(5-FUra), EN300-33909, Fluorouracil, meets USP testing specifications, C07649, D00584, 5-Fluorouracil, Vetec(TM) reagent grade, >=99%, Q238512, W-60379, (5-fluorouracil)5-Fluoro-1H-pyrimidine-2,4-dione, 5-Fluoro-1H-pyrimidine-2,4-dione(5-fluoro uracil), SR-01000075881-1, SR-01000075881-3, SR-01000075881-5, 5-Fluoro-1H-pyrimidine-2,4-dione (5-Fluorouracil), BRD-K24844714-001-02-1, BRD-K24844714-001-24-5, BRD-K24844714-001-25-2, 5-FLUOROPYRIMIDIN-2,4(1H,3H)-DIONE [WHO-IP], Z275128052, 5-Fluoro-1H-pyrimidine-2,4-dione(5-fluorouracil)(5-FU), 5-Fluorouracil, certified reference material, TraceCERT(R), Fluorouracil, British Pharmacopoeia (BP) Reference Standard, Fluorouracil, European Pharmacopoeia (EP) Reference Standard, Fluorouracil, United States Pharmacopeia (USP) Reference Standard, pyrimidine antimetabolite: inhibits nucleic acid replication; tetratogen, 2,4-Dihydroxy-5-fluoropyrimidine;5-FU;5-Fluoro-2,4(1H,3H)-pyrimidinedione, 5FU;5-FU;2,4-Dihydroxy-5-fluoropyrimidine;5-Fluoro-2,4(1H,3H)-pyrimidinedione, Fluorouracil, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9

Application

Fluorouracil (5-FU) is primarily used as a chemotherapeutic agent in the treatment of various cancers, including colorectal, breast, and pancreatic malignancies. It functions by inhibiting thymidylate synthase, leading to impaired DNA synthesis and cell death in rapidly dividing cells. Researchers also employ 5-FU in studying drug resistance mechanisms and combination therapies with other antineoplastic agents. Its role in topical formulations for actinic keratosis and superficial basal cell carcinoma is also well-documented.

Safety and Hazards

GHS Hazard Statements

• H301: Toxic if swallowed [Danger Acute toxicity, oral]
• H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]
• H360: May damage fertility or the unborn child [Danger Reproductive toxicity]
• H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Precautionary Statements

• P203, P260, P264, P270, P280, P301+P316, P318, P319, P321, P330, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (66.7%)
• Acute Tox. 4 (33.9%)
• Skin Irrit. 2 (36.3%)
• Eye Irrit. 2 (36.3%)
• STOT SE 3 (35.1%)
• Muta. 1B (35.1%)
• Repr. 1A (37.4%)
• Aquatic Chronic 3 (24.6%)

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