Vapreotide

Vapreotide (Sanvar) is a synthetic somatostatin analog. It is used in the treatment of esophageal variceal bleeding[1][2] in patients with cirrhotic liver disease and AIDS-related diarrhea.[3]

Vapreotide
Clinical data
Trade namesSanvar
Other namesH-D-Phe-Cys(1)-Tyr-D-Trp-Lys-Val-Cys(1)-Trp-NH2
Octastatin
ATC code
Pharmacokinetic data
Elimination half-life30 minutes
Identifiers
IUPAC name
  • D-phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-tryptophanamide (2->7)-disulfide
CAS Number
PubChem CID
PubChem SID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC57H70N12O9S2
Molar mass1131.38 g·mol−1
3D model (JSmol)
Density1.4 g/cm3
Boiling point1,540.9 °C (2,805.6 °F)
SMILES
  • CC(C)[C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)Cc2c[nH]c3c2cccc3)Cc4ccc(cc4)O)NC(=O)[C@@H](Cc5ccccc5)N)C(=O)N[C@@H](Cc6c[nH]c7c6cccc7)C(=O)N
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
  • Key:SWXOGPJRIDTIRL-DOUNNPEJSA-N

It is an 8 residue peptide with sequence H-D-Phe-Cys(1)-Tyr-D-Trp-Lys-Val-Cys(1)-Trp-NH2.

References
  1. Calès P (April 2008). "Vapreotide acetate for the treatment of esophageal variceal bleeding". Expert Review of Gastroenterology & Hepatology. 2 (2): 185–92. doi:10.1586/17474124.2.2.185. PMID 19072353.
  2. Fortune BE, Jackson J, Leonard J, Trotter JF (October 2009). "Vapreotide: a somatostatin analog for the treatment of acute variceal bleeding". Expert Opinion on Pharmacotherapy. 10 (14): 2337–42. doi:10.1517/14656560903207019. PMID 19708854.
  3. DrugBank DB04894



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