CAS 51-21-8|2,4-Dihydroxy-5-fluoropyrimidine|5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione|5-Fluoro-2,4(1H,3H)-pyrimidinedione|5-Fluorouracil|5-FU|fluorouracil|Adrucil|Carac|Fluro Uracil|Fluorople...

General Information

Structure

Molecular Formula

C₄H₃FN₂O₂

Molecular Mass

130.0772232

Exact Mass

130.01785557

Charge

InChI

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

InChIKey

GHASVSINZRGABV-UHFFFAOYSA-N

Canonic Smiles

Fc1c[nH]c(=O)[nH]c1=O

Isomeric Smiles

Fc1c(=O)[nH]c(=O)[nH]c1

Calculated Properties

JChem

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

Polarizability

9.588146

Polar Surface Area

58.2

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-0.58

LOG S

-1.35

Solubility (Water)

5.86e+00 g/l

Data Source

Names and Identifiers

Synonyms

2,4-Dihydroxy-5-fluoropyrimidine5-Fluoro-2,4(1H,3H)-pyrimidinedione5-Fluorouracil5-FUFluorouracilAdrucil(Fluorouracil)EfudexCaracFluorouracilFluoroplex5-Fluoropyrimidine-2,4(1H,3H)-dione5-Fluorouracil 99%5-Fluorouracil5-氟脲嘧啶5-氟-2,4(1H,3H)-嘧啶二酮2,4-二羟基-5-氟嘧啶5-fluoropyrimidine-2,4(1H,3H)-dione5-Fluoro Uracil TimazinU 8953Arumel5-Fluoropyrimidine-2,4-diolRo 2-97575-Fluoro-2,4(1H,3H)pyrimidinedioneFlurablastinQueroplexAdrucilUlup5-氟尿嘧啶 5-Fluorouracil

IUPAC name

5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

IUPAC Traditional name

fluorouracil

Brand Name

AdrucilCaracFluro UracilFluoroplexUlupTimazinEffludermPhtoruracilQueroplex5 FluorouracilFlurilKecimetonFluracilumEfudexFluriArumelFtoruracilEfurixCarzonalPhthoruracilFluracilEfudixFluoroblastinFUURF

Names and Identifiers

Registration numbers

CAS Number

51-21-8

Beilstein Number

127172

PubChem SID

248711651609638894650855724888466

EC Number

MDL Number

PubChem CID

Merck Index

Registration numbers

Properties

Safety Information

Download link

Pharmacology Properties

Antimetabolites

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00544

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]

Selleck Chemicals

S1209

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]

Apollo Scientific

PC4380

Antineoplastic agent. Not USP. Not for drug use.

MP Biomedicals

02101722

Crystalline
Purity: ~99%

Sigma Aldrich

858471

Packaging
5 g in glass bottle
Application
Inhibitor of DNA synthesis.1,2

47576

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

TRC

F596000

5-Fluoro Uracil is an active metabolite of Doxifluridine (D556750).

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Schuller, J., et al.: Cancer Chemother. Pharmacol., 45, 291 (1980)

• Pinedo, H., et al.: J. Clin. Oncol., 6, 1653 (1980)

• Bollag, W., et al.: Eur. J. Cancer, 16, 427 (1980)

• Ishikawa, T., et al.: Biochem. Pharmacol., 55, 1091 (1980)

• Antineoplastic agent. Not for drug use.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

IUPAC Traditional name

fluorouracil

Brand Name

AdrucilCaracFluro UracilFluoroplexUlupTimazinEffludermPhtoruracilQueroplex5 FluorouracilFlurilKecimetonFluracilumEfudexFluriArumelFtoruracilEfurixCarzonalPhthoruracilFluracilEfudixFluoroblastinFUURF

Registration numbers

CAS Number

51-21-8

Beilstein Number

127172

PubChem SID

248711651609638894650855724888466

EC Number

MDL Number

PubChem CID

Merck Index

References

PubChem Literature

From Data Sources

• 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

• Schuller, J., et al.: Cancer Chemother. Pharmacol., 45, 291 (1980)

• Pinedo, H., et al.: J. Clin. Oncol., 6, 1653 (1980)

• Bollag, W., et al.: Eur. J. Cancer, 16, 427 (1980)

• Ishikawa, T., et al.: Biochem. Pharmacol., 55, 1091 (1980)

• Antineoplastic agent. Not for drug use.

Bioactivity

PubChem BioAssay

Molecule Details

DrugBank

DB00544

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

Pharmacology

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

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]

Selleck Chemicals

S1209

Apollo Scientific

PC4380

Antineoplastic agent. Not USP. Not for drug use.

MP Biomedicals

02101722

Crystalline
Purity: ~99%