Skip to main content

Gemcitabine

ADVERTISEMENT
Identification
Molecular formula
C9H11F N3O4
CAS number
95058-81-4
IUPAC name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione
State
State

At room temperature, Gemcitabine is in a solid state as a crystalline powder.

Melting point (Celsius)
275.00
Melting point (Kelvin)
548.15
Boiling point (Celsius)
455.70
Boiling point (Kelvin)
728.85
General information
Molecular weight
299.19g/mol
Molar mass
299.1910g/mol
Density
1.7125g/cm3
Appearence

Gemcitabine is a white to off-white crystalline powder. It is typically very fine and may clump together slightly under standard conditions.

Comment on solubility

Solubility of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione

The solubility of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione can be influenced by several factors due to its complex structure. Here are some important aspects to consider:

  • Polarity: The presence of multiple hydroxyl groups in the tetrahydrofuran moiety contributes to the compound's polar nature. This polarity often enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups can form hydrogen bonds, which can further increase solubility in polar environments.
  • Environment Dependence: Depending on pH and the presence of other solutes, the solubility might change significantly. For instance, solubility in an acidic medium might differ from that in neutral or basic conditions.
  • Solvent Compatibility: It is likely that this compound exhibits better solubility in organic solvents like methanol or ethanol due to its structural characteristics.

As a general guideline, when evaluating solubility, the following can be considered:

  1. Testing in a variety of solvents to identify the best fit.
  2. Paying attention to temperature, which can affect solubility rates.
  3. Examining the influence of additional functional groups on solubility.

In summary, while 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione shows promise for solubility, detailed experimental studies are essential to determine precise solubility characteristics under various conditions.

Interesting facts

Interesting Facts about 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione

This compound presents a fascinating blend of organic chemistry and biological significance. It belongs to a class of compounds known for their role in pharmaceutical applications. Here are some interesting facts:

  • Structural Uniqueness: The compound features a complex structure that includes a tetrahydrofuran ring fused with a pyrimidine moiety. This unique combination enhances its reactivity and interaction with biological targets.
  • Biological Relevance: Compounds like this are often designed to inhibit enzymes or act on specific receptors in living organisms, making them crucial elements in drug discovery programs.
  • Stereochemistry: The stereochemistry represented by the (2R,3R,4S,5R) configuration is vital. In medicinal chemistry, subtle changes in stereochemistry can lead to significant changes in biological activity.
  • Fluorine Incorporation: The presence of the fluorine atom in the structural formula enhances lipophilicity, which can improve the compound's ability to cross biological membranes and reach its targets.
  • Potential Applications: Due to its complex nature, this compound could be explored in various therapeutic contexts, particularly within the realm of oncology, where pyrimidine derivatives have been studied for their antitumor properties.

In summary, 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione exemplifies the intricate relationship between chemical structure and biological function. Its study is not only a testament to the principles of organic synthesis but also to the ongoing efforts to develop effective therapeutic agents.

Synonyms
doxifluridine
5'-Deoxy-5-fluorouridine
5-fluoro-5'-deoxyuridine
Furtulon
3094-09-5
Uridine, 5'-deoxy-5-fluoro-
5'-Dfur
Flutron
Doxifluridina
Doxifluridinum
Fulturon
5'-Doxifluridine
Ro 219738
Furtulon (TN)
Uridine-5'-deoxy-5-fluoro-
Ro 21-9738
Doxifluridine [INN:JAN]
5-DFUR
Doxifluridinum [INN-Latin]
V1JK16Y2JP
Doxifluridina [INN-Spanish]
1-(beta-D-5-Desoxyribofuranoxyl)-5-fluoruracil
DTXSID2022967
CHEBI:31521
5'-dFUrd
EINECS 221-440-1
DOXIFLURIDINE [MI]
DOXIFLURIDINE [INN]
DOXIFLURIDINE [JAN]
NSC-758890
DOXIFLURIDINE [MART.]
DOXIFLURIDINE [WHO-DD]
RO-219738
DTXCID602967
NSC 758890
doxyfluridine
Doxifluridinum (INN-Latin)
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione
Doxifluridina (INN-Spanish)
DOXIFLURIDINE (MART.)
1-(.BETA.-D-5-DESOXYRIBOFURANOXYL)-5-FLUORURACIL
5'-fluoro-5'-deoxyuridine
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-pyrimidine-2,4-dione
221-440-1
5'dFUrd
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
CHEMBL1130
NCGC00093926-03
5'FDUR
MFCD00866530
SMR000326811
CAS-3094-09-5
SR-01000075886
Doxifluridine (5-Fluoro-5'-deoxyuridine)
Doxifluridine (Standard)
5-Deoxy-5'-fluorouridine
5-Fluoro-5`-deoxyuridine
UNII-V1JK16Y2JP
SCHEMBL8094
Doxifluridine (JP17/INN)
Lopac0_000537
MLS001332579
MLS001332580
MLS002172440
MLS002207077
HY-B0021R
HMS2090C22
HMS2231I05
HMS3261L15
HY-B0021
Tox21_111231
Tox21_500537
BDBM50132295
s2045
CAPECITABINE IMPURITY B (USP)
AKOS015852921
AKOS015896821
Tox21_111231_1
5-Fluoro-5'-deoxyuridine;doxifluridine
CCG-204627
CS-1270
DB12947
KS-5065
LP00537
SDCCGSBI-0050520.P002
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
NCGC00093926-01
NCGC00093926-02
NCGC00093926-05
NCGC00093926-11
NCGC00261222-01
Ro-21-9738
BP-58654
SRI-11552-08
SRI-11552_09
5''-Deoxy-5-Fluorouridine (5''-Dfur)
DB-185809
EU-0100537
NS00046999
D01309
F 8791
Q1253473
SR-01000075886-1
SR-01000075886-5
BRD-K58262659-001-09-7
Capecitabine impurity B, European Pharmacopoeia (EP) Reference Standard
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
1-((2R,5R)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione
1-((4S,2R,3R,5R)-3,4-Dihydroxy-5-methyloxolan-2-yl)-5-fluoro-1,3-dihydropyrimidine-2,4-dione
1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoropyrimidine-2,4(1H,3H)-dione (5'-Deoxy-5-fluorouridine)
Furtulon, Flutron, doxyfluridine, Doxifluridina, Doxifluridinum 5'-Doxifluridine, 5'dFUrd, 5-fluoro-5'-deoxyuridine