Vapreotide

Pharmaceutical drug

H01CB04 (WHO)

Pharmacokinetic dataElimination half-life30 minutesIdentifiers

IUPAC name

D-phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-tryptophanamide (2->7)-disulfide

CAS Number

103222-11-3

PubChem CID

23725064

PubChem SID

46506923

DrugBank

DB04894

ChemSpider

64425

UNII

2PK59M9GFF

KEGG

D06281

CompTox Dashboard (EPA)

DTXSID00883113

Chemical and physical dataFormulaC₅₇H₇₀N₁₂O₉S₂Molar mass1131.38 g·mol⁻¹3D model (JSmol)

Interactive image

Density1.4 g/cm³Boiling 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

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]

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

References

^ 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. S2CID 2681639.
^ 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. S2CID 24475861.
^ DrugBank DB04894