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Trifluridine

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Identification
Molecular formula
C10H11F3N2O5
CAS number
70-00-8
IUPAC name
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
State
State

At room temperature, Trifluridine is a solid. Its crystalline nature contributes to its powder form.

Melting point (Celsius)
164.00
Melting point (Kelvin)
437.15
Boiling point (Celsius)
425.00
Boiling point (Kelvin)
698.15
General information
Molecular weight
296.20g/mol
Molar mass
296.1980g/mol
Density
1.7650g/cm3
Appearence

Trifluridine appears as a white to pale yellow crystalline powder. It is sparingly soluble in water and slightly soluble in alcohols.

Comment on solubility

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

The compound C10H11F3N2O5 displays interesting solubility characteristics due to its unique molecular structure. Factors that influence its solubility include:

  • Polar functional groups: The presence of hydroxyl (–OH) groups enhances hydrogen bonding, facilitating solubility in polar solvents such as water.
  • Fluorine atoms: The trifluoromethyl group may impart some hydrophobic character, potentially limiting solubility in water while enhancing solubility in organic solvents like acetone or ethanol.
  • Overall molecular size: The relatively modest molecular weight suggests that the compound could be soluble in various solvent systems, though this would require empirical testing to confirm.

In summary, while C10H11F3N2O5 is expected to have reasonable solubility in polar solvents due to its hydroxyl functionalities, its trifluoromethyl group may hinder solubility in strictly aqueous environments. As always, empirical data is vital to understanding the solubility profile of such complex molecules.

Interesting facts

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

This unique compound presents a fascinating combination of functional groups and stereochemistry that contribute to its interesting chemical behavior and potential applications. Here are some noteworthy points about this compound:

  • Structural Complexity: The presence of the tetrahydrofuran ring contributes significantly to the compound's three-dimensional geometry, allowing for unique interactions with biological systems.
  • Fluorinated Features: The trifluoromethyl group (–CF3) is known for enhancing lipophilicity, which generally affects how compounds interact with cellular membranes.
  • Biological Relevance: Compounds containing pyrimidine rings have been extensively studied for their roles in biological systems, particularly as components of nucleic acids and in potential therapeutic agents.
  • Potential Medicinal Applications: The hydroxymethyl and hydroxy groups might be indicative of this compound's activity as a drug candidate, potentially acting as inhibitors or modulators in various biochemical pathways.
  • Stereoisomerism: The specific arrangement of its stereocenters indicates that the compound may exhibit different biological activities based on its isomeric form, making stereochemical consideration essential in drug development.
  • Research Interest: The compound's unique attributes make it a subject of ongoing research in fields such as medicinal chemistry, organic synthesis, and materials science.

As researchers continue to study this compound, its potential utility in pharmaceuticals and other applications may reveal even more intriguing advantages and uses in the chemical and biomedical domains!

Synonyms
Trifluridine
TRIFLUOROTHYMIDINE
70-00-8
Viroptic
5-Trifluorothymidine
Trifluoromethyldeoxyuridine
F3DThd
Trifluridina
Trifluridinum
Virophta
F3TDR
TFDU
5-(Trifluoromethyl)deoxyuridine
5-Trifluoromethyl-2-deoxyuridine
Trifluorothymine deoxyriboside
5-Trifluoromethyl-2'-deoxyuridine
2'-Deoxy-5-(trifluoromethyl)uridine
Trifluridinum [INN-Latin]
Trifluridina [INN-Spanish]
2'-Deoxy-5-trifluoromethyluridine
5-Trifluoro-2'-deoxythymidine
1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
alpha,alpha,alpha-Trifluorothymidine
CCRIS 2348
Trifluridine (Viroptic)
Thymidine, alpha,alpha,alpha-trifluoro-
Uridine, 2'-deoxy-5-(trifluoromethyl)-
UNII-RMW9V5RW38
EINECS 200-722-8
F3T
RMW9V5RW38
MFCD00006534
NSC 75520
NSC 529182
BRN 0568095
DTXSID4046602
CHEBI:75179
HSDB 8126
NSC-75520
NSC-529182
CHEMBL1129
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
MLS000028361
Trifluridine [USAN:USP:INN]
DTXCID2026602
NSC75520
2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-5-(trifluoromethyl)-
TAS-102 COMPONENT TRIFLURIDINE
S-95005 COMPONENT TRIFLURIDINE
Fluridine
SMR000058583
TFT
Trifluridinum (INN-Latin)
Trifluridina (INN-Spanish)
TRIFLURIDINE (MART.)
TRIFLURIDINE [MART.]
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
TRIFLURIDINE (USP-RS)
TRIFLURIDINE [USP-RS]
Trifluridine (USAN:USP:INN)
TRIFLURIDINE (EP MONOGRAPH)
TRIFLURIDINE [EP MONOGRAPH]
TRIFLURIDINE (USP MONOGRAPH)
TRIFLURIDINE [USP MONOGRAPH]
5-(Trifluoromethyl)-2'-deoxyuridine
CF3dUrd
Viroptic (TN)
Trifluridin
triflorothymidine
NSC529182
5 Trifluoromethyl 2' deoxyuridine
CAS-70-00-8
NCGC00166323-01
HS-0007
Trifluridinum (Latin)
Trifluridine (Standard)
Opera_ID_1810
5-Trifluoromethylthymidine
TRIFLURIDINE [MI]
TRIFLURIDINE [INN]
TRIFLURIDINE [JAN]
Trifluoromethyl Deoxyuridine
TRIFLURIDINE [USAN]
cid_6256
SCHEMBL3479
TRIFLURIDINE [VANDF]
MLS001148248
MLS006010219
TRIFLURIDINE [WHO-DD]
Trifluridine (JAN/USP/INN)
GTPL8697
cid_6708818
HY-A0061R
S01AD02
HMS2233N19
HMS3715C14
TRIFLURIDINE [ORANGE BOOK]
5-trifluoromethyl-2''-deoxyuridine
BCP09147
HY-A0061
Tox21_112411
BDBM50132298
Trifluorothymidine, >=99% (HPLC)
AKOS015919482
Tox21_112411_1
CCG-221056
CS-1602
DB00432
NT04884
TRIFLURIDINE COMPONENT OF LONSURF
NCGC00166323-02
NCGC00166323-16
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
BP-58659
SRI-10817-12
SRI-10817_14
S1778
SW199522-2
T2511
D00391
Thymidine, .alpha.,.alpha.,.alpha.-trifluoro-
EN300-24409722
SR-01000721911
Q2359590
SR-01000721911-2
BRD-K03243820-001-12-1
BRD-K03243820-001-22-0
BRD-K03243820-001-23-8
BRD-K03243820-001-25-3
Trifluridine, British Pharmacopoeia (BP) Reference Standard
Trifluridine;FTD;5-Trifluorothymidine;NSC 529182;NSC 75520
Trifluridine, United States Pharmacopeia (USP) Reference Standard
Trifluoridine;Trifluorothymine deoxyriboside;?,?,?-Trifluorothymidine;Trifluoro-D-thymidine
1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
1-((2R,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione
200-722-8