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Details

Stereochemistry ABSOLUTE
Molecular Formula C57H70N12O9S2.C23H16O6
Molecular Weight 1519.74
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VAPREOTIDE PAMOATE

SMILES

OC(=O)C1=C(O)C(CC2=C3C=CC=CC3=CC(C(O)=O)=C2O)=C4C=CC=CC4=C1.CC(C)[C@@H]5NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC6=CNC7=CC=CC=C67)NC(=O)[C@H](CC8=CC=C(O)C=C8)NC(=O)[C@H](CSSC[C@H](NC5=O)C(=O)N[C@@H](CC9=CNC%10=CC=CC=C9%10)C(N)=O)NC(=O)[C@H](N)CC%11=CC=CC=C%11

InChI

InChIKey=POMLZACZLQPRMY-NCACADTJSA-N
InChI=1S/C57H70N12O9S2.C23H16O6/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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/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);1-10,24-25H,11H2,(H,26,27)(H,28,29)/t40-,43+,44+,45+,46-,47+,48+,49+;/m1./s1

HIDE SMILES / InChI
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
Name Type Language
VAPREOTIDE PAMOATE
Common Name English
L-TRYPTOPHANAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-CYSTEINYL-, CYCLIC (2->7)-DISULFIDE, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (1:1)
Systematic Name English
VAPREOTIDE EMBONATE
Common Name English
Code System Code Type Description
PUBCHEM
87856398
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
FDA UNII
KJ1L137MPB
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
CAS
116430-61-6
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID30154323
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
CAS
124409-34-3
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
NON-SPECIFIC STOICHIOMETRY