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    Technical details about Thymectacin, learn more about the structure, uses, toxicity, action, side effects and more

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    Thymectacin

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    2D Structure
    1. Also known as: 232925-18-7, 2zrz4tsw3f, Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate, Nb-1011, L-alanine, n-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, methyl ester, Bvdu prodrug
    Molecular Formula
    C21H25BrN3O9P
    Molecular Weight
    574.3  g/mol
    InChI Key
    CFBLUORPOFELCE-BACVZHSASA-N
    FDA UNII
    2ZRZ4TSW3F
    Brivudine Phosphoramidate is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), brivudine is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis. Thus, TS retains activity and converts BVdUMP into cytotoxic metabolites. As key enzyme in the de novo synthesis of dTMP, TS is an enzyme critical to DNA biosynthesis and is overexpressed in many solid tumors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (2S)-2-[[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
    2.1.2 InChI
    InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1
    2.1.3 InChI Key
    CFBLUORPOFELCE-BACVZHSASA-N
    2.1.4 Canonical SMILES
    CC(C(=O)OC)NP(=O)(OCC1C(CC(O1)N2C=C(C(=O)NC2=O)C=CBr)O)OC3=CC=CC=C3
    2.1.5 Isomeric SMILES
    C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)/C=C/Br)O)OC3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    2ZRZ4TSW3F
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 232925-18-7

    2. 2zrz4tsw3f

    3. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

    4. Nb-1011

    5. L-alanine, N-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, Methyl Ester

    6. Bvdu Prodrug

    7. (2s)-methyl 2-(((((2r,3s,5r)-5-(5-((e)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

    8. Brivudine Phosphoramidate

    9. Unii-2zrz4tsw3f

    10. Schembl13904642

    11. Dtxsid00177862

    12. 5-(2-bromovinyl)-2'-deoxy-5'-uridyl-phenyl-alanylphosphoramidate, Trans-

    13. Db05116

    14. (e)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl Phenyl L-methoxyalaninylphosphoramidate

    15. E-5-(2-bromovinyl)-2'-deoxyuridine-5'-(l-methylalaninyl)-phenylphosphoramidate

    16. Hy-106168

    17. Cs-0025066

    18. J3.616.614b

    19. Q7799611

    20. (s)-2-({(2r,3s,5r)-5-[5-((e)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethoxy}-phenoxy-phosphorylamino)-propionic Acid Methyl Ester

    21. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromovinyl]-2,4-dioxo-pyrimidin-1-yl]-3-hydroxy-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate

    2.4 Create Date
    2006-04-28
    3 Chemical and Physical Properties
    Molecular Weight 574.3 g/mol
    Molecular Formula C21H25BrN3O9P
    XLogP31.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count11
    Exact Mass573.05118 g/mol
    Monoisotopic Mass573.05118 g/mol
    Topological Polar Surface Area153 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity909
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in colorectal cancer.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    NB1011 targets thymidylate synthase (TS), which catalyzes the transformation of E-5-(2-bromovinyl)-2'-deoxyuridine-5'-monophosphate (BVdUMP) into cytotoxic reaction products. Due to the elevated levels of TS expression in tumor cells compared to normal cells, these cytotoxic products are preferentially generated inside tumor cells, and, as expected, NB1011 is more toxic to cells with higher levels of TS expression. Therefore, NB1011 therapy should kill tumor cells without severely damaging normal cells.

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