Thiarabine
Basic information
- CAS
26599-17-7- Standard SMILES
Nc1ccn([C@@H]2S[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1- InChIKey
GAKJJSAXUFZQTL-CCXZUQQUSA-N- Molecular formula
- C9H13N3O4S
- Average molar mass
- 259.28 g/mol
- Monoisotopic mass
- 259.06267708
Overview
OSI-7836 is a member of the nucleoside class of cytotoxic drugs of which gemcitabine is the market leader. OSI Pharmaceuticals develops OSI-7836 as a next-generation gemcitabine. The anti-tumor activity of OSI-7836 appeares to be less schedule dependent than gemcitabine. It is also more active than ara-C (another clinically used nucleoside analog) in all nine models and more active than either paclitaxel or cisplatin in the two lung xenograft models tested. This drug shows no unexpected toxicities; those observed appeared to be similar to other nucleoside agents.
Names & identifiers
- Preferred name
- Thiarabine
- IUPAC
- 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidin-2-one
- English name
- THIARABINE
- Molecular formula
- C9H13N3O4S
- Molecular weight
- 259.28
Names & synonyms
THIARABINE26599-17-7Thio-Cytarabine4'-ThioaracytidineOSI-7836YCO2764D5Z2(1H)-Pyrimidinone, 4-amino-1-(4-thio-beta-D-arabinofuranosyl)-4'-thio-arabinofuranosylcytosine4-Amino-1-(4-thio-beta-D-arabinofuranosyl)-2(1H)-pyrimidinone4-thio-araCRefChem:189268GS7836
Show more names
4'-thioarabinoCytidineOSI-7836 (4'-thio-araC, T-araC)4-Amino-1-(4-thio-β-D-arabinofuranosyl)-2(1H)-pyrimidinone2(1H)-Pyrimidinone, 4-amino-1-(4-thio-β-D-arabinofuranosyl)-4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one
4'-THIO-1-BETA-D-ARABINOFURANOSYLCYTOSINE4-amino-1-((2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidine-2-thione hydrochlorideUNII-YCO2764D5Z4'-Thio-ara-C4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidin-2-oneOSI 7836THIARABINE [WHO-DD]4'-Thio-1- beta-D-arabinofuranosylcytosine
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 386
Physicochemical properties
- Boiling point
- 535 · 535.0±60.0 °C(Predicted)
- Density
- 1.9 · 1.90±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- Solid
- pka
- 13.41 · 13.41±0.70(Predicted)
- color
- White to off-white
- FDA UNII
- 2764 D5Z · YCO2764D5Z
- NCI Drug Dictionary
- thiarabine
Chemistry & industry
Pharmacology
Mechanism of Action
OSI-7836 appears to have a different mechanism of tumor growth inhibition blocking the cell division cycle at a different point (the G2 phase) than gemcitabine. The mechanism of action involves phosphorylation to the triphosphate form followed by incorporation into cellular DNA, leading to cell death.
Applications
UsesThiarabine (OSI-7836) shows potent anti-tumor activity and inhibition of DNA synthesis.
Related reactions
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Compound notes
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