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Compound InformationSONAR Target prediction
Name:

CYTARABINE

Unique Identifier:SPE01500217
MolClass: Checkout models in ver1.5 and ver1.0
Molecular Formula:
Molecular Weight:230.114 g/mol
X log p:2.451  (online calculus)
Lipinksi Failures0
TPSA41.9
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptors Count:8
Rotatable Bond Count:2
Canonical Smiles:NC1C=CN(C2OC(CO)C(O)C2O)C(=O)N=1
Source:synthetic
Therapeutics:antineoplastic, antiviral, antimetabolite
Generic_name:Cytarabine
Chemical_iupac_name:4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidin-2-one
Drug_type:Approved Drug
Kegg_compound_id:C02961
Drugbank_id:APRD00499
Melting_point:212-213oC
H2o_solubility:freely soluble
Logp:-2.712
Cas_registry_number:147-94-4
Drug_category:Immunosuppressive Agents; Antivirals; Antimetabolites; Antineoplastic Agents;
ATC:L01BC01
Indication:For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and
blast phase of chronic myelocytic leukemia.
Pharmacology:Cytarabine is an antineoplastic anti-metabolite used in the treatment of several
forms of leukemia including acute myelogenous leukemia and meningeal leukemia.
Anti-metabolites masquerade as purine or pyrimidine - which become the building
blocks of DNA. They prevent these substances becoming incorporated in to DNA during
the "S" phase (of the cell cycle), stopping normal development and division.
Cytarabine is metabolized intracellularly into its active triphosphate form
(cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple
mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA
repair through an effect on beta-DNA polymerase, and incorporation into DNA. The
latter mechanism is probably the most important. Cytotoxicity is highly specific for
the S phase of the cell cycle.
Mechanism_of_action:Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is
cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits
cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase)
and under certain conditions blocking the progression of cells from the G1 phase to
the S-phase. Although the mechanism of action is not completely understood, it
appears that cytarabine acts through the inhibition of DNA polymerase. A limited,
but significant, incorporation of cytarabine into both DNA and RNA has also been
reported.
Organisms_affected:Humans and other mammals

Found: 205 nonactive as graph: single | with analogs 2 3 4 5 6 7 8 9 10  Next >> [205]
Species: 4932
Condition: APC9
Replicates: 2
Raw OD Value: r im 0.6754±0.00735391
Normalized OD Score: sc h 0.9771±0.00267888
Z-Score: -1.2474±0.164341
p-Value: 0.215326
Z-Factor: -18.0147
Fitness Defect: 1.5356
Bioactivity Statement: Nonactive
Experimental Conditions
Library:Spectrum
Plate Number and Position:11|E2
Drug Concentration:50.00 nM
OD Absorbance:600 nm
Robot Temperature:23.10 Celcius
Date:2007-11-22 YYYY-MM-DD
Plate CH Control (+):0.0413±0.00072
Plate DMSO Control (-):0.6760250000000001±0.16785
Plate Z-Factor:0.1452
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DBLink | Rows returned: 232 3 4 Next >> 
596 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
6175 4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
6252 4-amino-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one hydrochloride
6253 4-amino-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
114682 4-amino-1-[(3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
122948 4-amino-1-[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

internal high similarity DBLink | Rows returned: 3
BTB 15125 1.0000
LOPAC 00787 1.0000
SPE01503431 1.0000

active | Cluster 3538 | Additional Members: 13 | Rows returned: 0

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