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Details

Stereochemistry ABSOLUTE
Molecular Formula C57H70N12O9S2
Molecular Weight 1131.371
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VAPREOTIDE

SMILES

CC(C)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CC4=CC=C(O)C=C4)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N[C@@H](CC5=CNC6=CC=CC=C56)C(N)=O)NC(=O)[C@H](N)CC7=CC=CC=C7

InChI

InChIKey=SWXOGPJRIDTIRL-DOUNNPEJSA-N
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

HIDE SMILES / InChI

Molecular Formula C57H70N12O9S2
Molecular Weight 1131.371
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Vapreotide (Sanvar) is cyclic octapeptide analog of somatostatin with higher metabolic stability than the parent hormone and developed by Debiopharm Group for the treatment of esophageal variceal bleeding in patients with cirrhotic liver disease and AIDS-related diarrhea. Somatostatin inhibits the secretion of vasodilatory peptides from the gastrointestinal tract, including glucagon, which has been shown to contribute to the maintenance of portal hypertension. While natural somatostatin has a very short half-life (3 min), the elimination half-life of vapreotide is reported to be approximately 10 times longer than that of its parent compound. Pharmacodynamic studies of healthy volunteers demonstrated suppression of gastric acid secretion and inhibition of the secretion of pancreatic enzyme, which is similar to somatostatin. Vapreotide has demonstrated efficacy in the early management of acute variceal hemorrhage but only based on combined primary endpoints of hemostasis and survival after 5 days. In addition, vapreotide’s efficacy is limited to only one major study performed in Europe and not yet in the United States. Although it did not show a significant reduction in mortality, vapreotide’s observed the effect on hemostasis, as well as its favorable safety profile. Adverse effects that occurred in the vapreotide trials were generally mild and primarily included gastrointestinal symptoms and alterations of the gastrointestinal hormonal system. Vapreotide not recommended for approval by an FDA Advisory Panel due to Insufficient evidence that the drug provided a benefit in the treatment for acute esophageal variceal bleeding.

Approval Year

PubMed

PubMed

TitleDatePubMed
Vapreotide: BMY 41606, RC 160, Sanvar.
2003
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:22:40 UTC 2023
Edited
by admin
on Fri Dec 15 16:22:40 UTC 2023
Record UNII
2PK59M9GFF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VAPREOTIDE
DASH   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-L-TRYPTOPHANAMIDE CYCLIC (2->7)-DISULFIDE
Common Name English
D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-L-TRYPTOPHANAMIDE CYCLIC (2->7)-DISULPHIDE
Common Name English
L-TRYPTOPHANAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-, CYCLIC (2->7)-DISULPHIDE
Common Name English
VAPREOTIDE [USAN]
Common Name English
BMY-41606
Code English
Vapreotide [WHO-DD]
Common Name English
VAPREOTIDE [MI]
Common Name English
RC-160
Code English
vapreotide [INN]
Common Name English
VAPREOTIDE [MART.]
Common Name English
L-TRYPTOPHANAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-, CYCLIC (2->7)-DISULFIDE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 175203
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
WHO-VATC QH01CB04
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
FDA ORPHAN DRUG 129699
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
FDA ORPHAN DRUG 129599
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
FDA ORPHAN DRUG 129899
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
NCI_THESAURUS C62799
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
FDA ORPHAN DRUG 175403
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
WHO-ATC H01CB04
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID00883113
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
EVMPD
SUB00026MIG
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
DRUG BANK
DB04894
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
INN
6485
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
CAS
103222-11-3
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
PUBCHEM
6918026
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
IUPHAR
2054
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
MERCK INDEX
m11393
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY Merck Index
FDA UNII
2PK59M9GFF
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
WIKIPEDIA
Vapreotide
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103975
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
NCI_THESAURUS
C1429
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
USAN
AA-109
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
SMS_ID
100000079074
Created by admin on Fri Dec 15 16:22:40 UTC 2023 , Edited by admin on Fri Dec 15 16:22:40 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> DERIVATIVE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY