Enocitabine
Basic information
- CAS
55726-47-1- Standard SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1- InChIKey
SAMRUMKYXPVKPA-VFKOLLTISA-N- Molecular formula
- C31H55N3O6
- Average molar mass
- 565.8 g/mol
- Monoisotopic mass
- 565.40908648
Overview
Enocitabine is an organic molecular entity.
Names & identifiers
- Preferred name
- Enocitabine
- IUPAC
- N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide
- English name
- Enocitabine
- Molecular formula
- C31H55N3O6
- Molecular weight
- 565.78
Names & synonyms
enocitabine55726-47-1SunrabinEnocitabinaEnocitabinumNSC-239336DTXSID60466829YVR68W306N-(1-beta-D-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamideDTXCID4026682behenoyl ara-Cbehenoyl cytarabine
Show more names
BH-ACCS-1807Enocitabine APIBEHENOYLCYTOSINE ARABINOSIDEN4-Behenoylcytosine arabinosiden(sup4)-behenoylcytosinearabinosideENOCITABINE 98.5+% ANTINEOPLASTIC DRUGS
N(4)-behenoyl ara-CNSC239336N(4)-behenoyl-1-beta-D-arabinofuranosylcytosineRefChem:920968N-(1-beta-D-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-docosanamideBHACN-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamideNCGC00167515-01
Database identifiers
- CAS
55726-47-1- PubChem CID
- 71734
- DTXSID
DTXSID6046682
Properties
Computed structural properties
- XLogP
- 9.2
- Topological polar surface area
- 132 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 23
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 774
Experimental & physicochemical properties
DrugsPharmaceutical
Physicochemical properties
- Melting point
- 141 · 141-142°C
- alpha
- 70 ° · D +70° (c = 1 in THF, 22°)
- Boiling point
- 630.87 °C · 630.87°C (rough estimate)
- Density
- 1.0967 · 1.0967 (rough estimate)
- refractive index
- 1.78 · 1.7800 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly, Heated), THF (Slightly, Heated, Soncited)
- pka
- 10.14 · 10.14±0.20(Predicted)
- form
- Solid
- color
- White to Off-White
- CAS DataBase Reference
- 55726 · 55726-47-1(CAS DataBase Reference)
- FDA UNII
- 9 YVR68W306 · 9YVR68W306
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Applications
DescriptionEnocitabine (NSC-239336, BHAC) is an antileukemic agent closely related to cytarabine. It appears more resistant to deamination than cytarabine, thus allowing greater in vivo phosphorylation into an active cytotoxic metabolite. Enocitabine is lipophilic, but the drug does not enter the cerebrospinal fluid and is concentrated in the bone marrow and red blood cells. It can be administered orally and appears to be more effective than the parent compound in preclinical models.
UsesAn antineoplastic. A derivative of Cytarabine.
Additional notes
DefinitionChEBI: Enocitabine is an organic molecular entity.
Related reactions
0 records
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Compound notes
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