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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

Vapreotide

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 Formula	C₅₇H₇₀N₁₂O₉S₂
Molecular Weight	1131.4 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	18
Exact Mass	1130.48301420 g/mol
Monoisotopic Mass	1130.48301420 g/mol
Topological Polar Surface Area	401 Å²
Heavy Atom Count	80
Formal Charge	0
Complexity	2080
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	8
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1