Fluorouracil
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MedKoo CAT#: 106613

CAS#: 51-21-8

Description: Fluorouracil, also known as 5-Fluorouracil and 5-FU, is a medication which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called the antimetabolites. It is also a pyrimidine analog. Fluorouracil has been given systemically for anal, breast, colorectal, oesophageal, stomach, pancreatic and skin cancers (especially head and neck cancers). It has also been given topically (on the skin) for actinic keratoses, skin cancers and Bowen's disease.

Chemical Structure

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Fluorouracil
CAS# 51-21-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 106613
Name: Fluorouracil
CAS#: 51-21-8
Chemical Formula: C4H3FN2O2
Exact Mass: 130.02
Molecular Weight: 130.080
Elemental Analysis: C, 36.93; H, 2.32; F, 14.61; N, 21.54; O, 24.60

Price and Availability

Size Price Availability Quantity
1g USD 70 Ready to ship
5g USD 150 Ready to ship
10g USD 250 Ready to ship
20g USD 450 Ready to ship
50g USD 850 Ready to ship
100g USD 1450 Ready to ship
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Synonym: 5-FU; Fluorouracil; 5-Fluorouracil; Trade name: Adrucil and many others.

IUPAC/Chemical Name: 5-fluoropyrimidine-2,4(1H,3H)-dione

InChi Key: GHASVSINZRGABV-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

SMILES Code: O=C1NC(C(F)=CN1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Fluorouracil (5-Fluorouracil, 5-FU, NSC 19893) is a DNA/RNA synthesis inhibitor, which interrupts nucleotide synthetic by inhibiting thymidylate synthase (TS) in tumor cells.
In vitro activity: The in vitro cellular uptake study showed that the dual-functionalized liposomes are capable of higher cellular uptake in glioblastoma (U87) and brain endothelial (bEnd.3) cells monolayer. In addition, dual-functionalized liposomes demonstrated significantly higher apoptosis in U87 cells. The liposomal nanoparticles showed excellent blood compatibility and in vitro cell viability, as studied by hemolysis and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, respectively. The 5-FU-loaded dual-functionalized liposomes demonstrated higher transport across the brain endothelial barrier and delivered 5-FU to tumor cells inside poly(lactic-co-glycolic acid)-chitosan scaffold (an in vitro brain tumor model), resulting in significant tumor regression. Reference: J Pharm Sci. 2018 Nov;107(11):2902-2913. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30055226/
In vivo activity: Short-term administration of 5-FU (3 days) increased gastrointestinal transit, induced acute intestinal inflammation and reduced the proportion of neuronal nitric oxide synthase-immunoreactive neurons. Long-term treatment (7, 14 days) resulted in delayed gastrointestinal transit, inhibition of colonic migrating motor complexes, increased short and fragmented contractions, myenteric neuronal loss and a reduction in the number of ChAT-immunoreactive neurons after the inflammation was resolved. Gross morphological damage to the colon was observed following both short- and long-term 5-FU treatment. Reference: Neurogastroenterol Motil. 2016 Dec;28(12):1861-1875. https://doi.org/10.1111/nmo.12890

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 15.0 11.31
Water 20.0 153.75

Preparing Stock Solutions

The following data is based on the product molecular weight 130.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Lakkadwala S, Singh J. Dual Functionalized 5-Fluorouracil Liposomes as Highly Efficient Nanomedicine for Glioblastoma Treatment as Assessed in an In Vitro Brain Tumor Model. J Pharm Sci. 2018 Nov;107(11):2902-2913. doi: 10.1016/j.xphs.2018.07.020. Epub 2018 Jul 25. PMID: 30055226; PMCID: PMC6215598. 2. Ruan J, Sun S, Cheng X, Han P, Zhang Y, Sun D. Mitomycin, 5-fluorouracil, leflunomide, and mycophenolic acid directly promote hepatitis B virus replication and expression in vitro. Virol J. 2020 Jul 1;17(1):89. doi: 10.1186/s12985-020-01339-5. PMID: 32611423; PMCID: PMC7331192.
In vivo protocol: 1. McQuade RM, Stojanovska V, Donald E, Abalo R, Bornstein JC, Nurgali K. Gastrointestinal dysfunction and enteric neurotoxicity following treatment with anticancer chemotherapeutic agent 5-fluorouracil. Neurogastroenterol Motil. 2016 Dec;28(12):1861-1875. doi: 10.1111/nmo.12890. Epub 2016 Jun 28. PMID: 27353132.

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1: Shah VV, Aldahan AS, Mlacker S, Alsaidan M, Samarkandy S, Nouri K. 5-Fluorouracil in the Treatment of Keloids and Hypertrophic Scars: A Comprehensive Review of the Literature. Dermatol Ther (Heidelb). 2016 Apr 22. [Epub ahead of print] Review. PubMed PMID: 27105629.

2: Pandey K, Dubey RS, Prasad BB. A Critical Review on Clinical Application of Separation Techniques for Selective Recognition of Uracil and 5-Fluorouracil. Indian J Clin Biochem. 2016 Mar;31(1):3-12. doi: 10.1007/s12291-015-0482-4. Epub 2015 Feb 15. Review. PubMed PMID: 26855482; PubMed Central PMCID: PMC4731362.

3: Metterle L, Nelson C, Patel N. Intralesional 5-fluorouracil (FU) as a treatment for nonmelanoma skin cancer (NMSC): A review. J Am Acad Dermatol. 2016 Mar;74(3):552-7. doi: 10.1016/j.jaad.2015.09.040. Epub 2015 Nov 11. Review. PubMed PMID: 26577512.

4: Cabourne E, Clarke JC, Schlottmann PG, Evans JR. Mitomycin C versus 5-Fluorouracil for wound healing in glaucoma surgery. Cochrane Database Syst Rev. 2015 Nov 6;11:CD006259. doi: 10.1002/14651858.CD006259.pub2. Review. PubMed PMID: 26545176.

5: Oyanagi H, Ichikawa H, Kosugi S, Banba T, Hanyu T, Hirashima K, Ishikawa T, Kameyama H, Kobayashi T, Minagawa M, Koyama Y, Wakai T. [Three cases of esophageal carcinoma achieved a pathological complete response after neoadjuvant chemotherapy with cisplatin and 5-fluorouracil]. Gan To Kagaku Ryoho. 2015 Apr;42(4):497-501. Review. Japanese. PubMed PMID: 25963701.

6: Li Q, Liu Y, Zhang HM, Huang YP, Wang TY, Li DS, Sun HZ. Influence of DPYD Genetic Polymorphisms on 5-Fluorouracil Toxicities in Patients with Colorectal Cancer: A Meta-Analysis. Gastroenterol Res Pract. 2014;2014:827989. doi: 10.1155/2014/827989. Epub 2014 Dec 28. Review. PubMed PMID: 25614737; PubMed Central PMCID: PMC4295351.

7: Ye J, Chen J, Ge L, Liu A, Zhou S. Effectiveness and safety of s-1-based therapy compared with 5-Fluorouracil-based therapy for advanced colorectal cancer: a meta-analysis. Gastroenterol Res Pract. 2014;2014:146530. doi: 10.1155/2014/146530. Epub 2014 Nov 30. Review. PubMed PMID: 25525426; PubMed Central PMCID: PMC4265705.

8: Wang WB, Yang Y, Zhao YP, Zhang TP, Liao Q, Shu H. Recent studies of 5-fluorouracil resistance in pancreatic cancer. World J Gastroenterol. 2014 Nov 14;20(42):15682-90. doi: 10.3748/wjg.v20.i42.15682. Review. PubMed PMID: 25400452; PubMed Central PMCID: PMC4229533.

9: Goldstein R, Yu D, Gillmore R, Thirlwell C, O'Donoghue P, Mayer A, Meyer T. Oxaliplatin/5-fluorouracil in advanced hepatocellular carcinoma: case report and single-center retrospective review. Future Oncol. 2014 Oct;10(13):2007-14. doi: 10.2217/fon.14.108. Epub 2014 Sep 11. Review. PubMed PMID: 25209630.

10: Polk A, Vistisen K, Vaage-Nilsen M, Nielsen DL. A systematic review of the pathophysiology of 5-fluorouracil-induced cardiotoxicity. BMC Pharmacol Toxicol. 2014 Sep 4;15:47. doi: 10.1186/2050-6511-15-47. Review. PubMed PMID: 25186061; PubMed Central PMCID: PMC4170068.

11: Iacovelli R, Pietrantonio F, Palazzo A, Maggi C, Ricchini F, de Braud F, Di Bartolomeo M. Incidence and relative risk of grade 3 and 4 diarrhoea in patients treated with capecitabine or 5-fluorouracil: a meta-analysis of published trials. Br J Clin Pharmacol. 2014 Dec;78(6):1228-37. doi: 10.1111/bcp.12449. Review. PubMed PMID: 24962653; PubMed Central PMCID: PMC4256612.

12: Aguado C, García-Paredes B, Sotelo MJ, Sastre J, Díaz-Rubio E. Should capecitabine replace 5-fluorouracil in the first-line treatment of metastatic colorectal cancer? World J Gastroenterol. 2014 May 28;20(20):6092-101. doi: 10.3748/wjg.v20.i20.6092. Review. PubMed PMID: 24876731; PubMed Central PMCID: PMC4033448.

13: Kang BW, Kim JG, Kwon OK, Chung HY, Yu W. Non-platinum-based chemotherapy for treatment of advanced gastric cancer: 5-fluorouracil, taxanes, and irinotecan. World J Gastroenterol. 2014 May 14;20(18):5396-402. doi: 10.3748/wjg.v20.i18.5396. Review. PubMed PMID: 24833869; PubMed Central PMCID: PMC4017054.

14: Papanastasopoulos P, Stebbing J. Molecular basis of 5-fluorouracil-related toxicity: lessons from clinical practice. Anticancer Res. 2014 Apr;34(4):1531-5. Review. PubMed PMID: 24692679.

15: Green E, Wilkins M, Bunce C, Wormald R. 5-Fluorouracil for glaucoma surgery. Cochrane Database Syst Rev. 2014 Feb 19;2:CD001132. doi: 10.1002/14651858.CD001132.pub2. Review. PubMed PMID: 24554410.

16: Endo C, Takagawa R, Chiba T, Kawamoto M, Konishi T, Honma Y, Minami Y, Watanabe J, Morita T, Mogaki M, Masui H. [A case of consciousness disorder induced by the syndrome of inappropriate secretion of antidiuretic hormone following cisplatin and 5-fluorouracil chemotherapy in a patient with esophageal cancer]. Gan To Kagaku Ryoho. 2013 Nov;40(12):2130-2. Review. Japanese. PubMed PMID: 24394036.

17: De Fendi LI, Arruda GV, Scott IU, Paula JS. Mitomycin C versus 5-fluorouracil as an adjunctive treatment for trabeculectomy: a meta-analysis of randomized clinical trials. Clin Experiment Ophthalmol. 2013 Nov;41(8):798-806. Review. PubMed PMID: 24308066.

18: Bahner JD, Bordeaux JS. Non-melanoma skin cancers: photodynamic therapy, cryotherapy, 5-fluorouracil, imiquimod, diclofenac, or what? Facts and controversies. Clin Dermatol. 2013 Nov-Dec;31(6):792-8. doi: 10.1016/j.clindermatol.2013.08.020. Review. PubMed PMID: 24160289.

19: Schmitt AR, Bordeaux JS. Solar keratoses: photodynamic therapy, cryotherapy, 5-fluorouracil, imiquimod, diclofenac, or what? Facts and controversies. Clin Dermatol. 2013 Nov-Dec;31(6):712-7. doi: 10.1016/j.clindermatol.2013.05.007. Review. PubMed PMID: 24160275.

20: van Kuilenburg AB, Maring JG. Evaluation of 5-fluorouracil pharmacokinetic models and therapeutic drug monitoring in cancer patients. Pharmacogenomics. 2013 May;14(7):799-811. doi: 10.2217/pgs.13.54. Review. PubMed PMID: 23651027.