Thiarabine - Moligand™, ≥98% , CAS No.26599-17-7

CAS: 26599-17-7 Cat. No.: T646680 Peso molecular: 259.28 PubChem CID: 168566

GRADE & PURITY Moligand™, ≥98%

Synonyms

HY-16496 | UNII-YCO2764D5Z | THIARABINE [WHO-DD] | 4'-thio-beta-D-arabinofuranosylcytosine | YCO2764D5Z | 4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one | 4'-THIO-1-.BETA.-D-ARABINOFURANOSYLCYTOSINE | T

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

Thiarabine (OSI-7836) shows potent anti-tumor activity and inhibition of DNA synthesis.

In Vivo

Thiarabine has demonstrated exceptional antitumor activity against numerous human tumor xenografts in mice, being superior to gemcitabine, clofarabine, or cytarabine. Unlike cytarabine, Thiarabine demonstrates excellent activity against solid tumor xenografts, suggesting that this agent has the kind of robust activity in animal models that leads to clinical utility. Thiarabine is effective orally (bioavailability of approximately 16%) and with once per day dosing: Two characteristics that distinguish it from cytarabine. Although both the structure and basic mechanism of action of Thiarabine are similar to that of cytarabine, there are many quantitative differences in the biochemical pharmacology of these two agents that can explain the superior antitumor activity of Thiarabine. Two important attributes are the long retention time of the 5'-triphosphate of thiarabine in tumor cells and its potent inhibition of DNA synthesis. The biochemical pharmacology of Thiarabine is also different from that of gemcitabine . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:DNA synthesis

Specifications

Sinónimos

HY-16496 | UNII-YCO2764D5Z | THIARABINE [WHO-DD] | 4'-thio-beta-D-arabinofuranosylcytosine | YCO2764D5Z | 4-amino-1-((2R, 3S, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one | 4'-THIO-1-.BETA.-D-ARABINOFURANOSYLCYTOSINE | T

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Thiarabine (OSI-7836) shows potent anti-tumor activity and inhibition of DNA synthesis.

Condiciones de almacenamiento de almacenamiento

Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: C1=CN(C(=O)N=C1N)C2C(C(C(S2)CO)O)O
• IUPAC Name: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidin-2-one
• InChIKey: GAKJJSAXUFZQTL-CCXZUQQUSA-N
• INCHI: 1S/C9H13N3O4S/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
• Isómeros SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](S2)CO)O)O
• CAS alternativo: 26599-17-7
• PubChem CID: 168566
• Términos de entrada MeSH: 4'-thio-arabinofuranosylcytosine;4'-thio-beta-D-arabinofuranosylcytosine;4-Amino-1-(4-thio-beta-D-arabinofuranosyl)-2(1H)-pyrimidinone;OSI-7836;thiarabine
• Peso molecular: 259.28

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Nucleoside and nucleotide analogues
      • Subclass Thionucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Nucleoside and nucleotide analogues
• Subclass: Thionucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Thionucleosides
• Alternative Parents: Pyrimidones Aminopyrimidines and derivatives Imidolactams Hydropyrimidines Thiolanes Heteroaromatic compounds Secondary alcohols Dialkylthioethers Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine thionucleoside - Aminopyrimidine - Pyrimidone - Hydropyrimidine - Pyrimidine - Imidolactam - Heteroaromatic compound - Thiolane - Secondary alcohol - Thioether - Azacycle - Organoheterocyclic compound - Dialkylthioether - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Alcohol - Amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as thionucleosides. These are nucleoside analogues that contain a thiolane or a thietane that is 1,3-disubstituted with a hydroxyl group and pyrimidine or purine base, at the 1- and 3-position, respectively.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

HFF (3142 Activities)

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Objetivos asociados (no humanos)

Human alphaherpesvirus 2 (4932 Activities)

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Cowpox virus (428 Activities)

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Vaccinia virus (4609 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 259.279 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 259.063 Da
• Monoisotopic Mass: 259.063 Da
• Topological Polar Surface Area: 145.000 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 386.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1