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Tenofovir

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Identification
Molecular formula
C9H14FN5O4P
CAS number
147127-20-6
IUPAC name
[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
State
State

At room temperature, Tenofovir is present in solid state. It is stable under standard storage conditions and does not readily degrade in its powder form.

Melting point (Celsius)
276.00
Melting point (Kelvin)
549.15
Boiling point (Celsius)
265.00
Boiling point (Kelvin)
538.15
General information
Molecular weight
287.21g/mol
Molar mass
287.2120g/mol
Density
1.5000g/cm3
Appearence

Tenofovir is typically a white to off-white crystalline powder, although the sodium salt form may appear slightly different in color and granularity. It is odorless and free-flowing.

Comment on solubility

Solubility of [(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate

The solubility of the compound [(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate can be quite intriguing due to its molecular structure and functional groups. Here are some important aspects to consider:

  • Hydrophilicity: The presence of the dihydrogen phosphate functional group contributes significantly to the hydrophilic nature of the compound, making it more soluble in aqueous environments.
  • Amine Group: The amino group present in the molecule can enhance solubility through hydrogen bonding with water molecules.
  • Furan Ring: The tetrahydrofuran ring, while having some hydrophobic characteristics, does not hinder solubility and can assist in stabilizing the structure in a solvent.

In general, biological relevance and applications of this compound suggest that its solubility may be favorable in physiological conditions, which is crucial for its function in biological processes. It's worth noting that:

  1. Solubility may vary with pH, so evaluating it across different pH levels can be essential.
  2. Temperature also plays a role; typically, increasing temperature can enhance solubility for many organic compounds.

To conclude, the complex interplay of functional groups within [(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate results in a compound that is likely to exhibit significant solubility in water, enabling its potential utility in various biochemical applications.

Interesting facts

Exploring the Complexities of a Unique Compound

The compound [(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate is a remarkable example of a multifunctional molecule that showcases the fascinating interplay between structure and function in biochemistry. Here are some intriguing aspects of this compound:

  • Structural Diversity: The compound features a complex stereochemistry, which includes multiple chiral centers. This structural diversity can lead to varying biological activities and interactions within living organisms.
  • Biological Relevance: This molecule is closely related to nucleosides, which are essential building blocks of nucleic acids (DNA and RNA). Therefore, it may play a significant role in genetic processes and cellular functions.
  • Phosphorylation Effects: The presence of dihydrogen phosphate groups suggests that it may participate in important biochemical reactions, including phosphorylation, which is crucial for energy transfer and signaling pathways in cells.
  • Potential Medical Applications: Compounds with similar structures have been explored for their therapeutic potential, particularly in the realms of antiviral and anticancer research. Understanding this compound could open doors to innovative treatments.
  • Fluorine's Role: The inclusion of a fluorine atom in the purine moiety can enhance the stability and bioavailability of the compound, making it a subject of interest in drug design.

This compound serves as a reminder of the rich complexity of chemical entities in biological systems, where subtle changes in structure can have profound effects on function. As research continues to uncover the mysteries of such molecules, the potential for significant scientific advancements remains vast.

Synonyms
fludarabine phosphate
75607-67-9
fludara
Fludarabine 5'-monophosphate
Oforta
Fludarabine monophosphate
2-F-ara-AMP
NSC-312887
CHEBI:63599
1X9VK9O1SC
2-Fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine
NSC 312887
2F-ara-AMP
NSC-328002
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)
DTXSID2023060
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-
FaraAMP
fluoro-ara-AMP
F-ara-AMP
RefChem:58476
DTXCID103060
9 beta-D-arabinofuranosyl-2-fluoroadenine monophosphate
NSC-118218
2-Fluoro-ARA AMP
Fludarabine (phosphate)
FAMP
MFCD00866418
((2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
C10H13FN5O7P
2-Fluoroadenine arabinoside 5'-monophosphate
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-b-D-arabinofuranosyl)-
9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate
75607-67-9 (phosphate)
Fludarabine Phosphate (Fludara)
NSC 328002
[(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Fludarabinephosphate
SMR002544683
SR-05000001945
UNII-1X9VK9O1SC
Beneflur
NSC312887
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-.beta.-D-arabinofuranosyl)-
Fludarabine phosphate; 2-Fluoro-9-(5-O-phosphono-ss-D-arabinofuranosyl)-9H-purin-6-amine
Fludara (TN)
fludarabine-phosphate
2-Fluoro-ara-AMP
Fludarabine phosphate [USAN:USP:BAN]
Fludarabine phosphate?
SCHEMBL3511
MLS003915617
MLS004774150
Fludarabine Phosphate(Fludara)
orb1300713
9-.beta.-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)
CHEMBL1096882
SCHEMBL29381896
HY-B0028R
Fludarabine phosphate (JAN/USP)
SHT-586
Fludarabine for system suitability
GIUYCYHIANZCFB-FJFJXFQQSA-N
GLXC-03004
HMS2094O11
Pharmakon1600-01505705
FLUDARABINE PHOSPHATE [JAN]
EX-A2028
Fludarabine (phosphate) (Standard)
HY-B0028
NSC-118218H
FLUDARABINE PHOSPHATE [USAN]
BDBM50248004
FLUDARABINE PHOSPHATE [VANDF]
HG1010
NSC759194
s1229
FLUDARABINE PHOSPHATE [MART.]
AKOS024464516
FLUDARABINE PHOSPHATE [USP-RS]
FLUDARABINE PHOSPHATE [WHO-DD]
BCP9000694
CCG-213521
CS-0861
NF01485
NSC-759194
SRI-5907-04
SRI-5907_05
SRI-5907_07
NCGC00182047-14
AS-14202
BP-43548
SY105999
BCP0726000268
FLUDARABINE 5'-MONOPHOSPHATE [MI]
FLUDARABINE PHOSPHATE [ORANGE BOOK]
SBI-0206893.P001
FLUDARABINE PHOSPHATE [EP MONOGRAPH]
FLUDARABINE PHOSPHATE [USP MONOGRAPH]
SW218146-2
D01907
EN300-269343
607F679
F792862
Q185916
SR-05000001945-1
SR-05000001945-4
BRD-K71106091-001-05-3
BRD-K71106091-001-06-1
BRD-K71106091-001-09-5
Z2235802254
9-beta-D-Arabinofuranosyl-2-fluoroadenine-5'-monophosphate
9-?-D-Arabinofuranosyl-2-fluoroadenine 5-phosphate;Fludarabine 5-monophosphate
[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
[rac-(2R,3S,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate