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    Etoposide Phosphate

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    2D Structure
    Also known as: 117091-64-2, Etopofos, Etopophos, Etopophos preservative free, Bmy 40481, Vepeside
    Molecular Formula
    C29H33O16P
    Molecular Weight
    668.5  g/mol
    InChI Key
    LIQODXNTTZAGID-OCBXBXKTSA-N
    FDA UNII
    528XYJ8L1N
    Etoposide Phosphate is a phosphate salt of a semisynthetic derivative of podophyllotoxin. Etoposide binds to the enzyme topoisomerase II, inducing double-strand DNA breaks, inhibiting DNA repair, and resulting in decreased DNA synthesis and tumor cell proliferation. Cells in the S and G2 phases of the cell cycle are most sensitive to this agent. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [4-[(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1
    2.1.3 InChI Key
    LIQODXNTTZAGID-OCBXBXKTSA-N
    2.1.4 Canonical SMILES
    CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)OP(=O)(O)O)OC)O)O
    2.1.5 Isomeric SMILES
    C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)OP(=O)(O)O)OC)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    528XYJ8L1N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bmy 40481-30

    2. Bmy-40481

    3. Bmy-40481-30

    4. Etophos

    5. Etopofos

    6. Etopophos

    2.3.2 Depositor-Supplied Synonyms

    1. 117091-64-2

    2. Etopofos

    3. Etopophos

    4. Etopophos Preservative Free

    5. Bmy 40481

    6. Vepeside

    7. Etoposide Phosphate [usan]

    8. Bmy-40481

    9. 528xyj8l1n

    10. Vp16

    11. Etophos

    12. Etoposide Phosphate (usan)

    13. Etoposide 4'-phosphate

    14. Unii-528xyj8l1n

    15. Etoposide-phosphate

    16. Etopophos (tn)

    17. Ncgc00185753-01

    18. Eposin Etopophos Vepesid Vp16

    19. Etoposide Phosphate (etopophos)

    20. Chembl1200645

    21. Etoposide Phosphate [mi]

    22. Schembl13318053

    23. Chebi:135867

    24. Etoposide Phosphate [vandf]

    25. Etoposide Phosphate [mart.]

    26. Ex-a3595

    27. Zinc3920020

    28. Bdbm50247889

    29. Etoposide Phosphate [usp-rs]

    30. Etoposide Phosphate [who-dd]

    31. Mfcd00270859

    32. Akos025311200

    33. Etoposide Phosphate [orange Book]

    34. Ncgc00185753-04

    35. 4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-beta-d-glucopyranoside), 4'-(dihydrogen Phosphate)

    36. As-12896

    37. Hy-13630

    38. Etoposide Phosphate [usp Monograph]

    39. Cs-0007496

    40. D04107

    41. 091e642

    42. J-003505

    43. Q27260984

    44. [4-[(5s,5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2

    45. 4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-.beta.-d-glucopyranoside), 4'-(dihydrogen Phosphate)

    46. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5-(3,5-dimethoxy-4-(phosphonooxy)phenyl)-9-((4,6-o-ethylidene-.beta.-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-, (5r-(5.alpha.,5a.beta.,8a.alpha.,9.beta.(r*)))-

    47. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5-(3,5-dimethoxy-4-(phosphonooxy)phenyl)-9-((4,6-o-ethylidene-beta-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-, (5r-(5alpha,5abeta,8aalpha,9beta(r*)))-

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 668.5 g/mol
    Molecular Formula C29H33O16P
    XLogP3-0.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count7
    Exact Mass668.15062196 g/mol
    Monoisotopic Mass668.15062196 g/mol
    Topological Polar Surface Area207 Ų
    Heavy Atom Count46
    Formal Charge0
    Complexity1140
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    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

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Topoisomerase Inhibitors [MoA]; Topoisomerase Inhibitor [EPC]