Vapreotide

DRACPC ID  DRACPC0060

Active Ingredients   Vapreotide

Description  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.

Synonyms  BMY-41606; Docrised; RC-160; Vapreotide

Type  Small Molecule

Disease  Pancreatic Cancer

Classification

  

Somatostatin analogs Peptide and derivative Cyclic Hormone and analogue

Structure Information


Molecular Formula  C57H70N12O9S2

Molecular Weight  1131.4

Active Sequence  FCYWKVCW

Sequence Length  8

Modification  N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

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

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)/t40-,43+,44+,45+,46-,47+,48+,49+/m1/s1

InChI_Key SWXOGPJRIDTIRL-DOUNNPEJSA-N

SMILES  CC([C@@H]1NC([C@@H](NC([C@H](NC([C@@H](NC([C@H](CSSC[C@H](NC1=O)C(N[C@H](C(N)=O)CC2=CNC3=CC=CC=C23)=O)NC([C@@H](CC4=CC=CC=C4)N)=O)=O)CC5=CC=C(C=C5)O)=O)CC6=CNC7=CC=CC=C67)=O)CCCCN)=O)C

External Codes


PubChem CID  71306

DrugBank Accession Number  DB04894

NCI Thesaurus Code  C1429  

UNII  2PK59M9GFF   GSRS

CAS  103222-11-3



Drug approval


Drug indication
    For the treatment of esophageal variceal bleeding in patients with cirrhotic liver disease and has also shown efficacy in the treatment of patients with AIDS-related diarrhea. It was being studied for the treatment of cancer.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00014651 Vapreotide in Pancreas Surgery: A Double-Blind, Placebo-Controlled, Randomized Study of Vapreotide to Prevent Post-Surgical Complications in Patients Undergoing Elective Pancreatic Resection Grant Application Title: Vapreotide to Prevent Complications of Pancreatic Resection Pancreatic Cancer; Perioperative/Postoperative Complications Phase 3 Supportive Care
NCT00331188 The Early Use of Sanvar® With Endoscopic Treatment for the Control of Acute Variceal Bleeding Due to Portal Hypertension Esophageal Varices; Portal Hypertension; Gastric Varices; Esophageal Bleeding Phase 3 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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