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    Talaporfin

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Laserphyrin, 220201-34-3, Taporfin sodium, Mono-l-aspartyl chlorin e6, Npe6, Ls-11
    Molecular Formula
    C38H37N5Na4O9
    Molecular Weight
    799.7  g/mol
    InChI Key
    JLWROAPZCOJYGT-OBJGRMLXSA-J
    FDA UNII
    L63605PZ70
    Talaporfin Sodium is an agent consisting of chlorin e6, derived from chlorophyll, and L-aspartic acid with photosensitizing activity. After intratumoral activation by light emitting diodes, taporfin sodium forms an extended high energy conformational state that generates singlet oxygen, resulting in free radical-mediated cell death. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    tetrasodium;(2S)-2-[[2-[(2S,3S)-7-carboxylato-3-(2-carboxylatoethyl)-17-ethenyl-12-ethyl-2,8,13,18-tetramethyl-2,3,23,24-tetrahydroporphyrin-5-yl]acetyl]amino]butanedioate
    2.1.2 InChI
    InChI=1S/C38H41N5O9.4Na/c1-7-20-16(3)24-12-26-18(5)22(9-10-32(45)46)35(42-26)23(11-31(44)41-30(37(49)50)15-33(47)48)36-34(38(51)52)19(6)27(43-36)14-29-21(8-2)17(4)25(40-29)13-28(20)39-24;;;;/h7,12-14,18,22,30,39-40H,1,8-11,15H2,2-6H3,(H,41,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52);;;;/q;4*+1/p-4/t18-,22-,30-;;;;/m0..../s1
    2.1.3 InChI Key
    JLWROAPZCOJYGT-OBJGRMLXSA-J
    2.1.4 Canonical SMILES
    CCC1=C(C2=CC3=C(C(=C(N3)C=C4C(C(C(=N4)C(=C5C(=C(C(=N5)C=C1N2)C)C(=O)[O-])CC(=O)NC(CC(=O)[O-])C(=O)[O-])CCC(=O)[O-])C)C)C=C)C.[Na+].[Na+].[Na+].[Na+]
    2.1.5 Isomeric SMILES
    CCC1=C(C2=CC3=C(C(=C(N3)C=C4[C@H]([C@@H](C(=N4)C(=C5C(=C(C(=N5)C=C1N2)C)C(=O)[O-])CC(=O)N[C@@H](CC(=O)[O-])C(=O)[O-])CCC(=O)[O-])C)C)C=C)C.[Na+].[Na+].[Na+].[Na+]
    2.2 Other Identifiers
    2.2.1 UNII
    L63605PZ70
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Laserphyrin

    2. Mono-l-aspartyl Chlorin E6

    3. Monoaspartyl Chlorin E6

    4. N-aspartyl Chlorin E6

    5. N-aspartylchlorin E6

    6. Npe6

    7. Talaporfin

    2.3.2 Depositor-Supplied Synonyms

    1. Laserphyrin

    2. 220201-34-3

    3. Taporfin Sodium

    4. Mono-l-aspartyl Chlorin E6

    5. Npe6

    6. Ls-11

    7. Talaporfin Sodium [usan]

    8. Talaporfin Tetrasodium Salt

    9. Me-2906

    10. L63605pz70

    11. Me 2906

    12. Tetrasodium (2s)-2-((((7s,8s)-3-carboxylato-7-(2-carboxylatoethyl)-13-ethenyl-18-ethyl-2,8,12,17-tetramethyl-7,8-dihydroporphyrin-5-yl)acetyl)amino)butanedioate

    13. Tetrasodium;(2s)-2-[[2-[(2s,3s)-7-carboxylato-3-(2-carboxylatoethyl)-17-ethenyl-12-ethyl-2,8,13,18-tetramethyl-2,3,23,24-tetrahydroporphyrin-5-yl]acetyl]amino]butanedioate

    14. Aptocine

    15. L-aspartic Acid, N-(((7s,8s)-3-carboxy-7-(2-carboxyethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21h,23h-porphin-5-yl)acetyl)-, Tetrasodium Salt

    16. Talaporfinsodium

    17. Laserphyrin (tn)

    18. Ls 11 (photosensitizer)

    19. Ls11

    20. Talaporfin Sodium (jan/usan)

    21. Talaporfin Sodium [jan]

    22. Chembl2107806

    23. Unii-l63605pz70

    24. Dtxsid70420519

    25. Talaporfin Sodium [mart.]

    26. Talaporfin Sodium [who-dd]

    27. Me2906

    28. At34139

    29. Talaporfin Tetrasodium Salt [mi]

    30. D01985

    31. Q27282754

    32. 220680-62-6

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 799.7 g/mol
    Molecular Formula C38H37N5Na4O9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count8
    Exact Mass799.21820490 g/mol
    Monoisotopic Mass799.21820490 g/mol
    Topological Polar Surface Area247 Ų
    Heavy Atom Count56
    Formal Charge0
    Complexity1340
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count5
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in macular degeneration.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

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

    Photosensitizing Agents

    Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

    5.2 Mechanism of Action

    Light Sciences Oncology (LSO) aims to en-light-en cancer patients. Light Sciences has developed Light Infusion Therapy (Litx) which is a novel treatment for solid tumors. The therapy involves inserting a flexible light-emitting diode (LED) into a tumor, followed by an injection of LS11 (talaporfin sodium), a light-activated drug. Once the LED activates LS11, molecular oxygen is converted into singlet oxygen, killing tissue within the LED's scope and shutting down the blood supply to the area. The treatment is designed for use on three types of cancers: hepatoma (liver cancer), metastatic colorectal cancer, and Gioma (brain tumor).