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    Locnartecan

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    2D Structure
    Also known as: Locnartecan, Hdc sn-38, Pen-866, 1472614-83-7, Sta 12-8666, Sdc-trap 0063
    Molecular Formula
    C49H49N7O9
    Molecular Weight
    880.0  g/mol
    InChI Key
    QTPZAEAYDWMVJO-GGCSAXROSA-N
    FDA UNII
    56DL1J49LR
    Locnartecan is a miniature drug conjugate composed of the irinotecan metabolite 7-ethyl-10-hydroxy-camptothecin (SN-38) conjugated, through a cleavable linker, to a ligand of chaperone protein heat shock protein 90 (Hsp90), with potential antineoplastic activity. Upon administration of locnartecan, the HSP90 ligand moiety targets HSP90, which allows the conjugate to penetrate, accumulate and be retained in the tumor cell. Once the linker is cleaved, the SN-38 moiety is released in a sustained manner. SN-38 then binds to and inhibits topoisomerase I by stabilizing the cleavable complex between topoisomerase I and DNA, which results in DNA breaks, inhibition of DNA replication and apoptosis. Compared to SN-38 alone, locnartecan preferentially targets, accumulates and is retained in the tumor cells due to its binding to Hsp90, which results in increased concentrations of SN-38 at the tumor site. This allows sustained release of SN-38 and leads to increased and prolonged efficacy while reducing toxicity to normal, healthy tissues. Hsp90, a chaperone protein upregulated and activated in a variety of tumor cells compared to normal healthy tissue, regulates the folding, stability and degradation of many oncogenic signaling proteins.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-[2-[5-[3-(2,4-dihydroxy-5-propan-2-ylphenyl)-5-oxo-1H-1,2,4-triazol-4-yl]indol-1-yl]ethyl]piperidine-1-carboxylate
    2.1.2 InChI
    InChI=1S/C49H49N7O9/c1-5-31-33-20-30(8-9-38(33)50-43-35(31)24-55-40(43)22-37-36(45(55)59)25-64-46(60)49(37,63)6-2)65-48(62)54-16-12-27(13-17-54)11-15-53-18-14-28-19-29(7-10-39(28)53)56-44(51-52-47(56)61)34-21-32(26(3)4)41(57)23-42(34)58/h7-10,14,18-23,26-27,57-58,63H,5-6,11-13,15-17,24-25H2,1-4H3,(H,52,61)/t49-/m0/s1
    2.1.3 InChI Key
    QTPZAEAYDWMVJO-GGCSAXROSA-N
    2.1.4 Canonical SMILES
    CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)CCN7C=CC8=C7C=CC(=C8)N9C(=NNC9=O)C1=CC(=C(C=C1O)O)C(C)C
    2.1.5 Isomeric SMILES
    CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)CCN7C=CC8=C7C=CC(=C8)N9C(=NNC9=O)C1=CC(=C(C=C1O)O)C(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    56DL1J49LR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Sta-12-8666

    2. Sta-8666

    2.3.2 Depositor-Supplied Synonyms

    1. Locnartecan

    2. Hdc Sn-38

    3. Pen-866

    4. 1472614-83-7

    5. Sta 12-8666

    6. Sdc-trap 0063

    7. 56dl1j49lr

    8. Hsp90-targeted Sn-38 Conjugate Pen-866

    9. [(19s)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-[2-[5-[3-(2,4-dihydroxy-5-propan-2-ylphenyl)-5-oxo-1h-1,2,4-triazol-4-yl]indol-1-yl]ethyl]piperidine-1-carboxylate

    10. Locnartecan [inn]

    11. Pen866

    12. Chembl4297475

    13. Pen-866 [who-dd]

    14. Schembl15522240

    15. Schembl22223739

    16. Sta-8666

    17. Sb19799

    18. (4s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin9-yl 4-(2-(5-(3-(2,4-dihydroxy-5-(propan-2-yl)phenyl)-5-oxo-1,5-dihydro-4h-1,2,4-triazol-4-yl)-1h-indol-1-yl)ethyl)piperidine-1-carboxylate

    19. 1-piperidinecarboxylic Acid, 4-(2-(5-(3-(2,4-dihydroxy-5-(1-methylethyl)phenyl)-1,5-dihydro-5-oxo-4h-1,2,4-triazol-4-yl)-1h-indol-1-yl)ethyl)-, (4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl

    20. 1-piperidinecarboxylic Acid, 4-(2-(5-(3-(2,4-dihydroxy-5-(1-methylethyl)phenyl)-1,5-dihydro-5-oxo-4h-1,2,4-triazol-4-yl)-1h-indol-1-yl)ethyl)-, (4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl Ester

    2.4 Create Date
    2019-01-15
    3 Chemical and Physical Properties
    Molecular Weight 880.0 g/mol
    Molecular Formula C49H49N7O9
    XLogP35.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count10
    Exact Mass879.35917617 g/mol
    Monoisotopic Mass879.35917617 g/mol
    Topological Polar Surface Area199 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1980
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1