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5-Fluorouracil

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Identification
Molecular formula
C4H3FN2O2
CAS number
51-21-8
IUPAC name
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
State
State

5-Fluorouracil is typically a solid at room temperature. It is normally supplied as a stable crystalline powder and requires storage in a cool, dry place.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.15
Boiling point (Celsius)
285.00
Boiling point (Kelvin)
558.15
General information
Molecular weight
130.08g/mol
Molar mass
130.0780g/mol
Density
1.4430g/cm3
Appearence

5-Fluorouracil is a white to off-white crystalline powder. It may appear in other solid forms such as needles or granules, depending on the method of production and processing.

Comment on solubility

Solubility of 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

The solubility of 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione (C4H3FN2O2) is an important characteristic that can influence its behavior in various chemical and biological systems. Generally, solubility is affected by several factors, including molecular structure, temperature, and the nature of the solvent.

Key Factors Affecting Solubility:

  • Polarity: The presence of functional groups such as hydroxyl (-OH) groups typically increases polarity, which enhances solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with water can significantly boost solubility. The hydroxy groups in this compound suggest a potential for strong interactions with water molecules.
  • Temperature: Solubility often increases with an increase in temperature for many compounds. However, this behavior is not universal and can vary based on the specific compound.

Moreover, it’s essential to consider that solubility can vary widely even with slight changes in molecular structure. As a result, testing solubility experimentally remains vital for an accurate understanding. In summary, while the theoretical basis provides insights, the actual solubility of this compound in various solvents should be determined through empirical methods to capture all the nuances of its chemical behavior.

Interesting facts

Interesting Facts about 5-Fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

This unique compound, a fluorinated pyrimidine derivative, has garnered attention in both medicinal chemistry and biochemistry due to its intriguing structural features and potential applications. Here are some noteworthy aspects:

  • Fluorine in Pharmaceuticals: The incorporation of fluorine into organic molecules often enhances their pharmacological properties, including metabolic stability and bioactivity. The presence of the fluorine atom in this compound may contribute to its effectiveness.
  • Biological Relevance: Pyrimidine derivatives are crucial in biological systems, playing a role in nucleic acid synthesis. This compound’s structure suggests it could be relevant in the development of nucleoside analogs, which are vital in antiviral and anticancer therapies.
  • Stereochemical Considerations: The compound's chiral centers (2R, 4S, and 5R) indicate significant stereochemistry that could influence its biological activity and interaction with enzymes or receptors. Understanding stereochemistry is essential in drug design, as different isomers can exhibit vastly different effects.
  • Potential Applications: Research suggests that similar compounds have the potential to act as inhibitors of certain enzymes, which could lead to breakthroughs in treating various diseases, particularly viral infections and cancer.
  • Research Interest: With advancements in synthetic methods, this compound represents an area of ongoing research. Scientists are continually exploring its biological properties, aiming to enhance its efficacy and reduce side effects through structure-activity relationship studies.

As noted by researchers, "the addition of functional groups can profoundly influence the molecular interactions in biological systems." This highlights the importance of compounds like 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione in the quest for novel therapeutics.

In summary, while this compound is just one of many in the vast realm of chemistry, its distinctive features and potential therapeutic applications make it a fascinating subject for ongoing study and exploration.

Synonyms
floxuridine
50-91-9
5-Fluorodeoxyuridine
2'-Deoxy-5-fluorouridine
Fluorodeoxyuridine
FUDR
5-Fluoro-2'-deoxyuridine
Floxuridin
FdUrd
Deoxyfluorouridine
Fluoruridine deoxyribose
5FdU
Floxiridina
Floxuridinum
5-Fluoro-2-desoxyuridine
5 Fluorodeoxyuridine
FDUR
5-fluoro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
beta-5-Fluoro-2'-deoxyuridine
5-Fluorouracil 2'-deoxyriboside
5-Fluoro-2-deoxyuridine
Floxuridinum [INN-Latin]
Uridine, 2'-deoxy-5-fluoro-
5-FdUrd
1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil
Floxiridina [INN-Spanish]
5-Fluorouracil deoxyriboside
NSC-27640
1beta-D-2'-Deoxyribofuranosyl-5-flurouracil
1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil
5-FUDR
floxidine
floxuridina
CHEBI:60761
HSDB 3227
EINECS 200-072-5
MFCD00006530
Uridine, 2'-deoxy-5-fluoro
UNII-039LU44I5M
BRN 0090221
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
DTXSID3023057
AI3-50691
039LU44I5M
CHEMBL917
Floxuridine [USAN:USP:INN]
MLS000069439
Uridine, 2'-deoxy-5'-fluoro-
DTXCID603057
5-Fluoro-2'-deoxy-beta-uridine
NSC 27640
5-24-06-00291 (Beilstein Handbook Reference)
NSC27640
Ro 5-0360
FdU
(+)-5-fluoro-2'-deoxyuridine
NCGC00023722-05
SMR000059051
5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion
Floxuridinum (INN-Latin)
Floxiridina (INN-Spanish)
FLOXURIDINE (MART.)
FLOXURIDINE [MART.]
FLOXURIDINE (USP-RS)
FLOXURIDINE [USP-RS]
Floxuridine (USAN:USP:INN)
FLOXURIDINE (USP IMPURITY)
FLOXURIDINE [USP IMPURITY]
FLOXURIDINE (USP MONOGRAPH)
FLOXURIDINE [USP MONOGRAPH]
CAS-50-91-9
5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
(+)-5-fluorodeoxyuridine
FUDR (TN)
5-floxuridine
Floxuridine,(S)
5-Fluoro-dUrd
Floxuridine (Fludara)
Fluorouridine Deoxyribose
Floxuridine (USP/INN)
FLOXURIDINE [MI]
2-Deoxy-5-fluorouridine
Opera_ID_1559
FLOXURIDINE [INN]
2-deoxy-5'-fluorouridine
FLOXURIDINE [HSDB]
FLOXURIDINE [USAN]
Epitope ID:138108
5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion [Czech]
5-Fluorouridine Deoxyribose
FLOXURIDINE [VANDF]
SCHEMBL4424
2''-deoxy-5-fluorouridine
2'-deoxy-5-fluoro uridine
5-fluoro-2''-deoxyuridine
FLOXURIDINE [WHO-DD]
5-Fluoro-2 inverted exclamation marka-deoxyuridine
MLS002695934
MLS006011768
5-fluoro-2''-Deoxy-uridine
2'-deoxy-5-fluoro-d-uridine
GTPL4801
FLOXURIDINE [ORANGE BOOK]
L01BC09
HMS2090I12
HMS2230N22
HMS3715A11
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
BCP02871
HY-B0097
Tox21_110892
BBL033765
BDBM50340678
s1299
STK801909
AKOS005622662
Tox21_110892_1
BCP9000691
CCG-220965
CS-1827
DB00322
ND02921
PS-7520
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
SRI-9246-15
SRI-9246_18
NCGC00023722-03
NCGC00023722-06
NCGC00023722-08
1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,3-dihydropyri midine-2,4-dione
136353-77-0
AC-16391
BP-58649
BCP0726000269
WR-138720
D2235
NS00015076
EN300-52649
D04197
SR-01000000001
Q5462356
SR-01000000001-2
1-BETA-D-2'-DEOXYRIBOFURANOSYL-5-FLUOROURACIL
BRD-K47832606-001-26-9
BRD-K47832606-001-30-1
5-Fluoro-2'-deoxyuridine, thymidylate synthase inhibitor
Z756475348
1-(beta-D-2-deoxy-erythro-pentofuranosyl)-5-fluorouracil
Floxuridine, United States Pharmacopeia (USP) Reference Standard
5-Fluoro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
200-072-5
5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
5-Fluoro-2'-deoxy-D-uridine;Floxuridine;2'-Deoxy-5-fluoro-D-uridine;5-Fluoro-2'-deoxyuridine