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Chemistry

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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
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 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


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