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51-21-8 molecular structure
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5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

ChemBase ID: 426
Molecular Formular: C4H3FN2O2
Molecular Mass: 130.0772232
Monoisotopic Mass: 130.01785557
SMILES and InChIs

SMILES:
Fc1c(=O)[nH]c(=O)[nH]c1
Canonical SMILES:
Fc1c[nH]c(=O)[nH]c1=O
InChI:
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey:
GHASVSINZRGABV-UHFFFAOYSA-N

Cite this record

CBID:426 http://www.chembase.cn/molecule-426.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
IUPAC Traditional name
fluorouracil
Brand Name
5 Fluorouracil
Adrucil
Arumel
Carac
Carzonal
Effluderm
Efudex
Efudix
Efurix
FU
Fluoroblastin
Fluoroplex
Fluracil
Fluracilum
Fluri
Fluril
Fluro Uracil
Ftoruracil
Kecimeton
Phthoruracil
Phtoruracil
Queroplex
Timazin
URF
Ulup
Synonyms
5-Fluoro-2,4(1H,3H)pyrimidinedione
5-Fluoropyrimidine-2,4-diol
Adrucil
Arumel
Flurablastin
Queroplex
Ro 2-9757
Timazin
U 8953
Ulup
5-Fluoro Uracil
5-fluoropyrimidine-2,4(1H,3H)-dione
Fluorouracil
5-Fluorouracil
2,4-Dihydroxy-5-fluoropyrimidine
5-Fluoro-2,4(1H,3H)-pyrimidinedione
5-Fluorouracil
Fluorouracil
5-FU
Carac
Efudex
Fluoroplex
Adrucil(Fluorouracil)
5-Fluoropyrimidine-2,4(1H,3H)-dione
5-Fluorouracil 99%
5-Fluorouracil
2,4-二羟基-5-氟嘧啶
5-氟-2,4(1H,3H)-嘧啶二酮
5-氟脲嘧啶
5-氟尿嘧啶
CAS Number
51-21-8
EC Number
200-085-6
MDL Number
MFCD00006018
Beilstein Number
127172
Merck Index
144181
PubChem SID
46508557
24888466
160963889
24871165
PubChem CID
3385

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.7786403  H Acceptors
H Donor LogD (pH = 5.5) -0.6778695 
LogD (pH = 7.4) -1.3501022  Log P -0.6558481 
Molar Refractivity 26.1722 cm3 Polarizability 9.588146 Å3
Polar Surface Area 58.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.58  LOG S -1.35 
Solubility (Water) 5.86e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
< 0.1 g/100 mL at 19 °C expand Show data source
DMSO expand Show data source
H2O: soluble10 mg/mL, clear expand Show data source
Water expand Show data source
Apperance
off-white to white powder expand Show data source
White Solid expand Show data source
Melting Point
130.5 °C expand Show data source
280-282°C(dec) expand Show data source
280-282°C expand Show data source
282-286 °C (dec.) expand Show data source
282-286 °C (dec.)(lit.) expand Show data source
282-286(dec.)°C expand Show data source
ca 282°C dec. expand Show data source
Boiling Point
190-200°C/0.1mm expand Show data source
Hydrophobicity(logP)
-0.8 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
Storage Warning
IRRITANT, TOXIC, CORROSIVE expand Show data source
Light Sensitive expand Show data source
Toxic/Light Sensitive/Keep Cold expand Show data source
RTECS
YR0350000 expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
2928 expand Show data source
UN2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
8 expand Show data source
Packing Group
3 expand Show data source
II expand Show data source
III expand Show data source
Australian Hazchem
2XE expand Show data source
Risk Statements
22 expand Show data source
61-22-48/22-68 expand Show data source
R:22-34 expand Show data source
Safety Statements
53-45 expand Show data source
S:26-27/28-36/37/39-46-64 expand Show data source
EU Classification
TC2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
true expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Hazard statements
H360-H341-H373-H302 expand Show data source
GHS Precautionary statements
P260-P281-P301+P312-P308+P313-P405-P501A expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Target
Antimetabolites expand Show data source
Purity
~99% expand Show data source
≥99.0% (HPLC) expand Show data source
97% expand Show data source
98.5% expand Show data source
98+% expand Show data source
99% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C4H3FN2O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Apollo Scientific Apollo Scientific Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02101722 external link
Crystalline
Purity: ~99%
DrugBank - DB00544 external link
Item Information
Drug Groups approved
Description A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]
Indication For the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
Pharmacology Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand.
Toxicity LD50=230mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption 28-100%
Half Life 10-20 minutes
Protein Binding 8-12%
Elimination Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour.
The remaining percentage of the administered dose is metabolized, primarily in the liver.
References
Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [Pubmed]
Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Apollo Scientific Ltd - PC4380 external link
Antineoplastic agent. Not USP. Not for drug use.
Selleck Chemicals - S1209 external link
Research Area: Cancer
Biological Activity:
Fluorouracil (5-FU or f5U) is a chemotherapy drug that is a pyrimidine analog which is used in the treatment of cancer. It works through noncompetitive inhibition of thymidylate synthase. Due to its noncompetitive nature and effects on thymidine synthesis, 5-FU is frequently referred to as the "suicide inactivator". It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. [1] Fluorouracil IC50 values were observed across the National Cancer Institute NCI60 panel of human tumor cell lines, which exhibit a mean IC50 of 17.6 μM, with a range of 1–501 μM. [2]
Sigma Aldrich - 858471 external link
Packaging
5 g in glass bottle
Application
Inhibitor of DNA synthesis.1,2
Sigma Aldrich - 47576 external link
Other Notes
Potent antineoplastic agent. Its determination in tissue with microbore HPLC and fluorescence detection1; Metabolised to fluoro-2′-deoxyuridine monophosphate which inhibits DNA synthesis by blocking thymidylate synthetase2
Toronto Research Chemicals - F596000 external link
5-Fluoro Uracil is an active metabolite of Doxifluridine (D556750).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
  • • Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed
  • • http://en.wikipedia.org/wiki/Fluorouracil
  • • Bollag, W., et al.: Eur. J. Cancer, 16, 427 (1980)
  • • Pinedo, H., et al.: J. Clin. Oncol., 6, 1653 (1980)
  • • Ishikawa, T., et al.: Biochem. Pharmacol., 55, 1091 (1980)
  • • Schuller, J., et al.: Cancer Chemother. Pharmacol., 45, 291 (1980)
  • • Antineoplastic agent. Not for drug use.
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PATENTS

PATENTS

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INTERNET

INTERNET

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