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Cytarabine hydrochloride

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Identification
Molecular formula
C9H14ClN3O5
CAS number
69-74-9
IUPAC name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one;hydrochloride
State
State
Cytarabine hydrochloride is in a solid state at room temperature. It is typically administered in a sterile form for medical use, specifically in the treatment of cancers.
Melting point (Celsius)
215.50
Melting point (Kelvin)
488.65
Boiling point (Celsius)
930.00
Boiling point (Kelvin)
1 203.15
General information
Molecular weight
243.20g/mol
Molar mass
243.1980g/mol
Density
1.6500g/cm3
Appearence
Cytarabine hydrochloride appears as a white to off-white crystalline powder. It is hygroscopic and should be handled in controlled environments to prevent atmospheric moisture absorption.
Comment on solubility

Solubility of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one;hydrochloride

The solubility of the compound 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one;hydrochloride (C9H14ClN3O5) is quite notable and can be described as follows:

  • The presence of the hydrochloride form often enhances solubility in polar solvents such as water due to the ionic nature of the chloride ions.
  • Generally, compounds containing hydroxyl groups (as seen here with the tetrahydrofuran moiety) tend to exhibit increased hydrophilicity, facilitating their solubility.
  • In the case of pyrimidine derivatives, they often display variable solubility properties depending on the substituents present. The amino and hydroxyl groups can contribute to stronger interactions with solvent molecules.

In summary, this compound is expected to be soluble in polar solvents and could potentially be poorly soluble in non-polar solvents. This behavior can be attributed to its complex structure featuring both hydrophilic functional groups and the ionic characteristics from its hydrochloride form.

Interesting facts

Interesting Facts about 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one; hydrochloride

This compound is an intriguing example of a pyrimidine derivative with significant biological implications. It is notably recognized for its role as a *nucleotide analogue*, which is crucial in various biochemical pathways. Here are some interesting aspects of this compound:

  • Antiviral Activity: Research has shown that compounds related to pyrimidine derivatives can exhibit antiviral properties, potentially aiding in the treatment of several viral infections.
  • Structural Complexity: The compound features a versatile sugar moiety, specifically a tetrahydrofuran ring, which enhances its ability to interact with biological targets.
  • Stereochemistry: It has stereocenters at positions 2, 3, 4, and 5, making its three-dimensional structure essential for its biological activity. The stereochemical configuration is crucial for its binding affinity to specific receptors.
  • Hydrophilicity: The presence of multiple hydroxyl groups renders this compound highly hydrophilic, influencing its solubility and interaction in aqueous environments.
  • Potential Therapeutic Applications: Given its structural similarities to natural nucleotides, there is ongoing research exploring its potential in treating *cancers* and *viral diseases*, by disrupting the synthesis of nucleic acids in pathogens.

As a chemist or a student in the field of chemistry, understanding compounds like this one expands your knowledge of how molecular structures affect biological functions. Exploring the modifications in drug design based on compounds like this offer exciting opportunities for new therapeutic strategies. As the famous chemist Linus Pauling stated, "The best way to understand a complex system is to study its parts." This exploration helps decode the intricate relationship between structure and function in medicinal chemistry.

Synonyms
CYTARABINE HYDROCHLORIDE
69-74-9
Cytosine arabinoside hydrochloride
Cytarabine HCl
Ara-C hydrochloride
1-beta-D-Arabinofuranosylcytosine hydrochloride
Cytosar hydrochloride
Spongocytidine hydrochloride
Arabitin hydrochloride
Aracytin hydrochloride
Cytarabin hydrochloride
Aracytidine hydrochloride
Arabinosylcytosine hydrochloride
Cytarabine hydrochloride [USAN]
Cytarabine (hydrochloride)
U-19920A
CCRIS 4774
Arabinosyl cytosine hydrochloride
Cytosine-1-beta-D-arabinofuranoside hydrochloride
EINECS 200-713-9
DTXSID5024891
AI3-52344
1beta-D-Arabinofuranosylcytosine hydrochloride
Cytosine beta-D-arabinofuranoside hydrochloride
MFCD00012839
NSC-63878
1beta-D-Arabinofuranosylcytosine monohydrochloride
33K3DB6591
1-beta-D-Arabinofuranosylcytosine monohydrochloride
Cytosine, 1-beta-D-arabinofuranosyl-, hydrochloride
Cytosine, 1-beta-D-arabinofuranosyl-, monhydrochloride
Cytosine, 1beta-D-arabinofuranosyl-, monohydrochloride
69-74-9 (HCL)
MLS000028466
DTXCID104891
29363-79-9
Cytarabine hydrochloride (USAN)
Arabinofuranosylcytosine hydrochloride
2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-, monohydrochloride
AC 1075
4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride
Cytosine, 1-beta-D-arabinofuranosyl-, monohydrochloride
CYTARABINE HYDROCHLORIDE [WHO-DD]
SMR000058432
2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-arabinofuranosyl-, monohydrochloride
1-.BETA.-D-ARABINOFURANOSYLCYTOSINE MONOHYDROCHLORIDE
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
Spongocytidine-hydrochloride
NSC63878
SR-01000075773
UNII-33K3DB6591
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one hydrochloride
Ara-C HCl
Opera_ID_1542
Arabinocytidine hydrochloride
SCHEMBL67288
MLS001148147
MLS002207299
CHEMBL1256472
Cytosine Arabinosine Hydrochloride
GLXC-15916
Tox21_300488
Tox21_500316
HY-13605A
s5582
AKOS015896936
AKOS015960559
AKOS015995277
CCG-221620
LP00316
NA05780
SCH-900242
CAS-69-74-9
NCGC00093762-01
NCGC00254321-01
NCGC00261001-01
AC-11705
AC-32195
BA164338
Cytarabine hydrochloride - Bio-X trade mark
DB-025611
Cytosine-beta-D-arabinofuranose hydrochloride
EU-0100316
NS00076327
1-(b-D-Arabinofuranosyl)cytosine hydrochloride
A51105
C 6645
Cytosine beta -D-arabinofuranoside hydrochloride
D03637
1-(beta-d-arabino-furanosyl)-cytosine hydrochloride
SR-01000075773-1
Q27256279
Cytosine beta-D-arabinofuranoside hydrochloride, crystalline
Cytosine ?-D-arabinofuranoside hydrochloride;Ara-C.hydrochloride
4-Amino-1-beta-d-arabinofuranosyl-2(1H)-pyrimidinone hydrochloride
2(1H)-Pyrimidinone,4-amino-1-b-D-arabinofuranosyl-,hydrochloride (1:1)
4-AMINO-1-BETA-D-ARABINOFURANOSYL-2(1H)-PYRIMIDINONE MONOHYDROCHLORIDE
Arabinocytidine hydrochloride; Arabinosylcytosine hydrochloride; Ara-C hydrochloride
200-713-9
4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride
4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride(1:x)
4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-onehydrochloride(1:x)
Cytosine ?-D-arabinofuranoside hydrochloride;1-(?-D-Arabinofuranosyl)cytosine hydrochloride;Ara-C.hydrochloride