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    Plitidepsin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Aplidine, Aplidin, 137219-37-5, Dehydrodidemnin b, Y76id234hw, Chebi:90205
    Molecular Formula
    C57H87N7O15
    Molecular Weight
    1110.3  g/mol
    InChI Key
    UUSZLLQJYRSZIS-LXNNNBEUSA-N
    FDA UNII
    Y76ID234HW
    Plitidepsin is a cyclic depsipeptide isolated from the marine tunicate Aplidium albicans. Plitidepsin displays a broad spectrum of antitumor activities, inducing apoptosis by triggering mitochondrial cytochrome c release, initiating the Fas/DC95, JNK pathway and activating caspase 3 activation. This agent also inhibits elongation factor 1-a, thereby interfering with protein synthesis, and induces G1 arrest and G2 blockade, thereby inhibiting tumor cell growth.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C57H87N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-34,36,39-44,46-47,49,66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
    2.1.3 InChI Key
    UUSZLLQJYRSZIS-LXNNNBEUSA-N
    2.1.4 Canonical SMILES
    CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(=O)C)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]3CCCN3C(=O)C(=O)C)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    Y76ID234HW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aplidin

    2. Aplidine

    3. Dehydrodidemnin B

    2.3.2 Depositor-Supplied Synonyms

    1. Aplidine

    2. Aplidin

    3. 137219-37-5

    4. Dehydrodidemnin B

    5. Y76id234hw

    6. Chebi:90205

    7. Plitidepsin (inn)

    8. Plitidepsin [inn]

    9. (2s)-n-[(2r)-1-[[(3s,6s,8s,12s,13r,16s,17r,20s,23s)-13-[(2s)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

    10. Plitidepsin [inn:ban]

    11. Plitidepsina

    12. Plitidepsine

    13. Plitidepsium

    14. Unii-y76id234hw

    15. Aplidine [mi]

    16. Plitidepsin [mi]

    17. Plitidepsin [mart.]

    18. Plitidepsin [who-dd]

    19. Didemnin A, N-(1-(1,2-dioxopropyl)-l-prolyl)-

    20. Chembl451930

    21. 2-9-didemnin B, 2-(1-(1,2-dioxopropyl)-l-proline)-

    22. Schembl13413427

    23. Gtpl11396

    24. (s)-n-((r)-1-(((3s,6r,7s,10r,11s,15s,17s,20s,25as)-10-((s)-sec-butyl)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-1,4,8,13,16,18,21-heptaoxodocosahydro-15h-pyrrolo[2,1-f][1,15]dioxa[4,7,10,20]tetraazacyclotricosin-7-yl)amino)-4-methyl-1-oxopentan-2-yl)-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

    25. At23636

    26. Db04977

    27. Hy-16050

    28. Cs-0006129

    29. D11032

    30. Q4779975

    31. Y-100032

    32. (2s)-n-[(2r)-1-[[(3s,6s,8s,12s,13r,16s,17r,20s,23s)-13-[(2s)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl) Methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

    33. 1-(2-oxopropanoyl)-l-prolyl-n-[(3s,6r,7s,10r,11s,15s,17s,20s,25as)-10-[(2s)-butan-2-yl]-11-hydroxy-3-(4-methoxybenzyl)-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-15-(propan-2-yl)docosahydro-15h-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]-n(2)-methyl-d-leucinamide

    34. 3,6-anhydro(n-((2s,4s)-4-((3s,4r,5s)-3-hydroxy-4-((n-(2-oxopropanoyl)-l-prolyl-n-methyl-d-leucyl-l-threonyl)amino)-5-methylheptanoyloxy)-2,5-dimethyl-3-oxohexanoyl)-l-leucyl-l-prolyl-n,o-dimethyl-l-tyrosine)

    35. L-tyrosine, 1-(1,2-dioxopropyl)-l-prolyl-n-methyl-d-leucyl-l-threonyl-(3s,4r,5s)-4-amino-3-hydroxy-5-methylheptanoyl-(2s,4s)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl-l-leucyl-l-prolyl-n,o-dimethyl-, (8-3)-lactone

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 1110.3 g/mol
    Molecular Formula C57H87N7O15
    XLogP35.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count15
    Exact Mass1109.62601509 g/mol
    Monoisotopic Mass1109.62601509 g/mol
    Topological Polar Surface Area285 Ų
    Heavy Atom Count79
    Formal Charge0
    Complexity2200
    Isotope Atom Count0
    Defined Atom Stereocenter Count12
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Intended for the treatment of various forms of cancer.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX57 - Plitidepsin

    5.2 Metabolism/Metabolites

    Hepatic

    5.3 Mechanism of Action

    Aplidine inhibits the growth and induces apoptosis in MOLT-4 cells through the indirect inhibition of VEGF secretion which blocks the VEGF/VEGFR-1 autocrine loop necessary for the growth of these cells.