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    Vidarabine Monophosphate

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 29984-33-6, Vidarabine monophosphate, Ara-amp, Vidarabine phosphate [usan], Cl-808, 9-(5-o-phosphono-beta-d-arabinofuranosyl)adenine
    Molecular Formula
    C10H14N5O7P
    Molecular Weight
    347.22  g/mol
    InChI Key
    UDMBCSSLTHHNCD-UHTZMRCNSA-N
    FDA UNII
    106XV160TZ
    An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7+,10-/m1/s1
    2.1.3 InChI Key
    UDMBCSSLTHHNCD-UHTZMRCNSA-N
    2.1.4 Canonical SMILES
    C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N
    2.1.5 Isomeric SMILES
    C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    106XV160TZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 9-(5-o-phosphono-beta-d-arabinofuranosyl)-9h-purin-6-amine

    2. Adenine Arabinoside Monophosphate

    3. Ara Amp

    4. Ara-amp

    5. Arabinofuranosyladenine Monophosphate

    6. Monophosphate, Adenine Arabinoside

    7. Monophosphate, Arabinofuranosyladenine

    8. Monophosphate, Vidarabine

    9. Phosphate, Vidarabine

    10. Vidarabine Monophosphate

    2.3.2 Depositor-Supplied Synonyms

    1. 29984-33-6

    2. Vidarabine Monophosphate

    3. Ara-amp

    4. Vidarabine Phosphate [usan]

    5. Cl-808

    6. 9-(5-o-phosphono-beta-d-arabinofuranosyl)adenine

    7. Ci-808

    8. 9h-purin-6-amine, 9-(5-o-phosphono-beta-d-arabinofuranosyl)-

    9. 9-(5-o-phosphono-beta-d-arabinofuranosyl)-9h-purin-6-amine

    10. Adenine-9-beta-d-arabinofuranoside-5'-monophosphate

    11. Adenine Arabinoside Monophosphate

    12. Vidarabine-5'-monophosphate

    13. 106xv160tz

    14. Arabinosyladenine Monophosphate

    15. Adenine Arabinose-5'-phosphate

    16. Nsc-127223

    17. Araamp

    18. 5'-arabinosyladenine Monophosphate

    19. 9h-purin-6-amine, 9-(5-o-phosphono-b-d-arabinofuranosyl)-

    20. Adenine Arabinoside 5'-monophosphate

    21. D-arabinosyladenine 5'-monophosphate

    22. Adenine Arabinonucleoside 5'-phosphate

    23. [(2r,3s,4s,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

    24. Vidarabine Phosphate (usan)

    25. 9h-purin-6-amine,9-(5-o-phosphono-b-d-arabinofuranosyl)-

    26. Vidarabinemonophosphate

    27. Vidarabine 5'-monophosphate

    28. Einecs 249-990-8

    29. Nsc 127223

    30. 9h-purin-6-amine, 9-(5-o-phosphono-.beta.-d-arabinofuranosyl)-

    31. Unii-106xv160tz

    32. Nsc127223

    33. 9-beta-d-arabinofuranosyladenine 5'-phosphate

    34. 9-beta-d-arabinofuranosyladenine Monophosphate

    35. Arabino-amp

    36. 9-beta-d-arabinofuranosyladenine 5'-monophosphate

    37. Mfcd00069723

    38. 9-beta-d-arabinofuranosyladenine 5'-(dihydrogen Phosphate)

    39. Adenine, 9beta-d-arabinofuranosyl-, 5'-(dihydrogen Phosphate)

    40. Schembl144996

    41. Chembl1230732

    42. Hy-b0277a

    43. Adenosine Arabinoside-5'-phosphate

    44. Dtxsid401009318

    45. Adenine, 9-beta-d-arabinofuranosyl-, 5'-(dihydrogen Phosphate)

    46. Bcp10479

    47. Zinc2126310

    48. Hg1004

    49. Vidarabine Phosphate [mart.]

    50. Vidarabine Phosphate [who-dd]

    51. Akos015915213

    52. Ac-5505

    53. Am84913

    54. ((2r,3s,4s,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl Dihydrogen Phosphate

    55. [(2r,3s,4s,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl Dihydrogen Phosphate

    56. As-70487

    57. Ara-adenosine-5'-monophosphate (ara-amp)

    58. Cs-0083442

    59. D06299

    60. 9-(b-d-arabinofuranosyl)adenine5'-monophosphate

    61. 9-(b-d-arabinofuranosyl)adenine 5'-monophosphate

    62. 9-beta-d-arabinofuranosyladenine-5'-monophosphate

    63. 984a336

    64. A820136

    65. 9-(.beta.-d-arabinofuranosyl)adenine-5'-phosphate

    66. Q6607436

    67. W-202244

    68. 9-beta-d-arabinofuranosyl-adenine-5'-monophosphate

    69. 9h-purin-6-amine, 9-(5-o-phosphono-b-d-arabinofuranosyl)-;

    70. 9-.beta.-d-arabinofuranosyladenine 5'-(dihydrogen Phosphate)

    71. {[(2r,3s,4s,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic Acid

    72. A5o

    2.4 Create Date
    2005-07-12
    3 Chemical and Physical Properties
    Molecular Weight 347.22 g/mol
    Molecular Formula C10H14N5O7P
    XLogP3-3.5
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count4
    Exact Mass347.06308480 g/mol
    Monoisotopic Mass347.06308480 g/mol
    Topological Polar Surface Area186 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity481
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.)