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    Vapreotide

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Vapreotide, 103222-11-3, Rc 160, Bmy 41606, L-tryptophanamide, d-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-valyl-l-cysteinyl-, cyclic (2?7)-disulfide, acetate (1:?);l-tryptophanamide, d-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-valyl-l-cysteinyl-, cyclic (2?7)-disulfide, acetate (1:?), Rc-160 (vapreotide)
    Molecular Formula
    C57H70N12O9S2
    Molecular Weight
    1131.4  g/mol
    InChI Key
    SWXOGPJRIDTIRL-UHFFFAOYSA-N
    Vapreotide is a synthetic cyclic octapeptide analogue of somatostatin with direct and indirect antitumor effects. Vapreotide binds to somatostatin receptors (SSTR), specifically SSTR-2 and to SSTR-5 with a lesser affinity, in the similar behaviors as other octapeptide somatostatin analogues. Like octreotide, this agent has direct and indirect antitumor effects via inhibiting the release of growth hormone and other peptides that regulate release of insulin, gastrointestinal hormones. Furthermore, vapreotide may also be useful for inducing hemostasis in cases of acute hemorrhage of the upper gastrointestinal tract.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    10-(4-aminobutyl)-N-[1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-19-[(2-amino-3-phenylpropanoyl)amino]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
    2.1.2 InChI
    InChI=1S/C57H70N12O9S2/c1-32(2)49-57(78)68-48(55(76)64-44(50(60)71)26-35-28-61-41-16-8-6-14-38(35)41)31-80-79-30-47(67-51(72)40(59)24-33-12-4-3-5-13-33)56(77)65-45(25-34-19-21-37(70)22-20-34)53(74)66-46(27-36-29-62-42-17-9-7-15-39(36)42)54(75)63-43(52(73)69-49)18-10-11-23-58/h3-9,12-17,19-22,28-29,32,40,43-49,61-62,70H,10-11,18,23-27,30-31,58-59H2,1-2H3,(H2,60,71)(H,63,75)(H,64,76)(H,65,77)(H,66,74)(H,67,72)(H,68,78)(H,69,73)
    2.1.3 InChI Key
    SWXOGPJRIDTIRL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC=CC=C5)N)C(=O)NC(CC6=CNC7=CC=CC=C76)C(=O)N
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. D-phe-cys-tyr-d-trp-lys-val-cys-trp-nh2

    2. D-phenylalanyl-cysteinyl-tyrosyl-d-tryptophyl-lysyl-valyl-cysteinyl-tryptophanamide

    3. Octastatin

    4. Rc 160

    5. Rc-160

    6. Vapreotide

    2.2.2 Depositor-Supplied Synonyms

    1. Vapreotide

    2. 103222-11-3

    3. Rc 160

    4. Bmy 41606

    5. L-tryptophanamide, D-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-valyl-l-cysteinyl-, Cyclic (2?7)-disulfide, Acetate (1:?);l-tryptophanamide, D-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-valyl-l-cysteinyl-, Cyclic (2?7)-disulfide, Acetate (1:?)

    6. Rc-160 (vapreotide)

    7. Rc-160

    8. Vapreotide (usan/inn)

    9. Gtpl2054

    10. Schembl6369050

    11. Bdbm82464

    12. Bcp21232

    13. Cas_71306

    14. Mfcd30489723

    15. Nsc_71306

    16. Akos015896024

    17. Ft-0652516

    18. D06281

    19. L001100

    20. Sanvar Ir; Vapreotidum; Rc 160; Rc-160; Rc160

    21. (4r,7s,10s,13r,16s,19r)-13-((1h-indol-3-yl)methyl)-n-((s)-1-amino-3-(1h-indol-3-yl)-1-oxopropan-2-yl)-19-((r)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-(4-hydroxybenzyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide

    22. (4r,7s,10s,13s,16s,19r)-10-(4-aminobutyl)-n-[(2r)-1-amino-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 1131.4 g/mol
    Molecular Formula C57H70N12O9S2
    XLogP33.6
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count18
    Exact Mass1130.48301420 g/mol
    Monoisotopic Mass1130.48301420 g/mol
    Topological Polar Surface Area401 Ų
    Heavy Atom Count80
    Formal Charge0
    Complexity2080
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count8
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Analgesics

    Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

    Antineoplastic Agents

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

    4.2 ATC Code

    H - Systemic hormonal preparations, excl. sex hormones and insulins

    H01 - Pituitary and hypothalamic hormones and analogues

    H01C - Hypothalamic hormones

    H01CB - Somatostatin and analogues

    H01CB04 - Vapreotide