U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C57H70N12O9S2.C2H4O2
Molecular Weight 1191.423
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VAPREOTIDE ACETATE

SMILES

CC(O)=O.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=KBIZSMHYSQUHDH-NCACADTJSA-N
InChI=1S/C57H70N12O9S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/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

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 15:56:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:22 GMT 2023
Record UNII
5562377HFV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VAPREOTIDE ACETATE
MI   USAN   WHO-DD  
USAN  
Official Name English
L-TRYPTOPHANAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-, CYCLIC (2->7)-DISULFIDE, MONOACETATE (SALT)
Systematic Name English
OCTASTATIN ACETATE
Common Name English
VAPREOTIDE ACETATE [USAN]
Common Name English
DP-05-094
Code English
RC-160 ACETATE
Code English
DOCRISED
Brand Name English
VAPREOTIDE MONOACETATE
Common Name English
VAPREOTIDE ACETATE [MI]
Common Name English
SANVAR
Brand Name English
L-TRYPTOPHANAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-, CYCLIC (2->7)-DISULFIDE, ACETATE (SALT)
Systematic Name English
BMY-41606 ACETATE
Code English
Vapreotide acetate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C62799
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
Code System Code Type Description
PUBCHEM
6918025
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
CAS
849479-74-9
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
NON-SPECIFIC STOICHIOMETRY
DRUG BANK
DBSALT000535
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
NCI_THESAURUS
C95320
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
FDA UNII
5562377HFV
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
CAS
116430-60-5
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
EVMPD
SUB12617MIG
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103975
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
MERCK INDEX
m11393
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY Merck Index
SMS_ID
100000078765
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
USAN
XX-38
Created by admin on Fri Dec 15 15:56:22 GMT 2023 , Edited by admin on Fri Dec 15 15:56:22 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY