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
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
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.
Originator
Approval Year
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:22:40 GMT 2023
by
admin
on
Fri Dec 15 16:22:40 GMT 2023
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Record UNII |
2PK59M9GFF
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
175203
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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WHO-VATC |
QH01CB04
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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FDA ORPHAN DRUG |
129699
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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FDA ORPHAN DRUG |
129599
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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FDA ORPHAN DRUG |
129899
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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NCI_THESAURUS |
C62799
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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FDA ORPHAN DRUG |
175403
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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WHO-ATC |
H01CB04
Created by
admin on Fri Dec 15 16:22:40 GMT 2023 , Edited by admin on Fri Dec 15 16:22:40 GMT 2023
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Code System | Code | Type | Description | ||
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DTXSID00883113
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SUB00026MIG
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DB04894
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6485
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103222-11-3
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6918026
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2054
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m11393
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PRIMARY | Merck Index | ||
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2PK59M9GFF
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Vapreotide
Created by
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CHEMBL2103975
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C1429
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AA-109
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100000079074
Created by
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PRIMARY |
Related Record | Type | Details | ||
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PARENT -> DERIVATIVE |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |