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    Vidarabine Monohydrate

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    2D Structure
    Also known as: 24356-66-9, Fa2dm6879k, Ci 673, Vidarabine (usan), (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol hydrate, Vidarabine [usan]
    Molecular Formula
    C10H15N5O5
    Molecular Weight
    285.26  g/mol
    InChI Key
    ZTHWFVSEMLMLKT-CAMOTBBTSA-N
    FDA UNII
    FA2DM6879K
    A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the VACCINIA VIRUS and varicella zoster virus.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;hydrate
    2.1.2 InChI
    InChI=1S/C10H13N5O4.H2O/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10;/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13);1H2/t4-,6-,7+,10-;/m1./s1
    2.1.3 InChI Key
    ZTHWFVSEMLMLKT-CAMOTBBTSA-N
    2.1.4 Canonical SMILES
    C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N.O
    2.1.5 Isomeric SMILES
    C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N.O
    2.2 Other Identifiers
    2.2.1 UNII
    FA2DM6879K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 9 Beta Arabinofuranosyladenine

    2. 9 Beta D Arabinofuranosyladenine

    3. 9-beta-arabinofuranosyladenine

    4. 9-beta-d-arabinofuranosyladenine

    5. Adenine Arabinoside

    6. Alpha Ara A

    7. Alpha D Arabinofuranosyladenine

    8. Alpha-ara A

    9. Alpha-d-arabinofuranosyladenine

    10. Ara A

    11. Ara-a

    12. Arabinofuranosyladenine

    13. Arabinoside, Adenine

    14. Arabinosyladenine

    15. Beta Ara A

    16. Beta-ara A

    17. Vidarabine

    18. Vira A

    19. Vira-a

    20. Viraa

    2.3.2 Depositor-Supplied Synonyms

    1. 24356-66-9

    2. Fa2dm6879k

    3. Ci 673

    4. Vidarabine (usan)

    5. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Hydrate

    6. Vidarabine [usan]

    7. (2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;hydrate

    8. Vidarabine [jan]

    9. Vidarabine (monohydrate)

    10. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol Hydrate

    11. Adenine Arabinofuranoside Hydrate

    12. 9-beta-d-arabinofuranosyl-9h-purine-6-amine Monohydrate

    13. Drg-0058

    14. Unii-fa2dm6879k

    15. 9-beta-d-arabinofuranosyladenine Monohydrate

    16. Vidarabineh2o

    17. Vidarabine H2o

    18. Adenine, 9-beta-d-arabinofuranosyl-, Monohydrate

    19. Vidarabine [usan:usp:inn:ban:jan]

    20. 9h-purin-6-amine, 9-beta-d-arabinofuranosyl-, Monohydrate

    21. Vira-a (tn)

    22. Vidarabine [vandf]

    23. Schembl2929

    24. Vidarabine [mart.]

    25. Chebi:9978

    26. Vidarabine [orange Book]

    27. Dtxsid10947210

    28. Vidarabine [usp Impurity]

    29. 9h-purin-6-amine, 9-.beta.-d-arabinofuranosyl-, Monohydrate

    30. Vidarabine Monohydrate [mi]

    31. Hy-n6666

    32. Mfcd00150980

    33. S5297

    34. Akos025312428

    35. Ccg-267319

    36. Nsc 757383

    37. Cs-0083211

    38. 9-beta-d-arabino Furanosyl Adenine Monohydrate

    39. Adenine 9-beta-d-arabinofuranoside Monohydrate

    40. C07195

    41. D00406

    42. T72143

    43. Vidarabine (200 Mg)g-2939ug/mg(ai)

    44. 9-pentofuranosyl-9h-purin-6-amine--water (1/1)

    45. J-015462

    46. 9-.beta.-d-arabinofuranosyladenine Monohydrate

    47. 9h-purin-6-amine,9-b-d-arabinofuranosyl-,hydrate(1:1)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 285.26 g/mol
    Molecular Formula C10H15N5O5
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count2
    Exact Mass285.10731860 g/mol
    Monoisotopic Mass285.10731860 g/mol
    Topological Polar Surface Area141 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity335
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antimetabolites

    Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

    Antiviral Agents

    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. (See all compounds classified as Antiviral Agents.)