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5-Fluorouracil

CAT: 0804-HY-90006-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-90006-01Size:50 mg
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Description
5-Fluorouracil (5-FU) is an analogue of uracil and a potent antitumor agent. 5-Fluorouracil affects pyrimidine synthesis by inhibiting thymidylate synthetase thus depleting intracellular dTTP pools. 5-Fluorouracil induces apoptosis and can be used as a chemical sensitizer[1][2]. 5-Fluorouracil also inhibits HIV[3].
CAS Number
51-21-8
Product Name Alternative
5-FU
UNSPSC
12352005
Hazard Statement
H301, H351
Target
Apoptosis; Endogenous Metabolite; HIV; Nucleoside Antimetabolite/Analog
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/5-Fluorouracil.html
Purity
99.99
Solubility
1 M Ammonium hydroxide : 50 mg/mL (ultrasonic) |DMSO : 50 mg/mL (ultrasonic) |H2O : 10 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C(N1)NC=C(F)C1=O
Molecular Formula
C4H3FN2O2
Molecular Weight
130.08
Precautions
H301, H351
References & Citations
[1]Han R, et al. Amphiphilic dendritic nanomicelle-mediated co-delivery of 5-fluorouracil and NSC 123127 for enhanced therapeutic efficacy. J Drug Target. 2016 Jun 29:1-28. [Epub ahead of print]|[2]McQuade RM, et al. Gastrointestinal dysfunction and enteric neurotoxicity following treatment with anticancer chemotherapeutic agent 5-fluorouracil. Neurogastroenterol Motil. 2016 Jun 28.|[3]Zeng Q, et al. Knockdown of NFBD1/MDC1 enhances chemosensitivity to NSC 119875 or 5-fluorouracil in nasopharyngeal carcinoma CNE1 cells. Mol Cell Biochem. 2016 Jul;418 (1-2) :137-46.|[4]Yin L, et al. Antitumor effects of oncolytic herpes simplex virus type 2 against colorectal cancer in vitro and in vivo. Ther Clin Risk Manag. 2017 Feb 7;13:117-130.|[5]Jones DH, et al. Ten-Year and Beyond Follow-up After Treatment With Highly Purified Liquid-Injectable Silicone for HIV-Associated Facial Lipoatrophy: A Report of 164 Patients. Dermatol Surg. 2019 Jul;45 (7) :941-948.|[6]Snyder SM, et al. Initial Experience with Topical Fluorouracil for Treatment of HIV-Associated Anal Intraepithelial Neoplasia. J Int Assoc Physicians AIDS Care (Chic) . 2011;10 (2) :83-88.|[7]Pek Yee Lum, et al. Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes. Cell. 2004 Jan 9;116 (1) :121-37.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
HIV

Chemical Information

5-Fluorouracil

Fluorouracil can cause developmental toxicity according to an independent committee of scientific and health experts.

CAS Number51-21-8
PubChem CID3385
IUPAC Name5-fluoro-1H-pyrimidine-2,4-dione
Molecular FormulaC4H3FN2O2
Molecular Weight130.08
XLogP-0.9
Topological Polar Surface Area58.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count9
Formal Charge0
Complexity199
SMILES
C1=C(C(=O)NC(=O)N1)F
InChI
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey
GHASVSINZRGABV-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 5-Fluorouracil
CAS: 51-21-8
CID: 3385
Formula: C4H3FN2O2
MW: 130.08
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight130.08
XLogP3-0.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass130.01785550
Monoisotopic Mass130.01785550
Topological Polar Surface Area58.2 Ų
Heavy Atom Count9
Formal Charge0
Complexity199
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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