Vapreotide (trifluoroacetate salt)

Vapreotide is a peptide neurokinin-1 receptor (NK1) antagonist and analog of somatostatin (IC50 = 330 nM in a radioligand binding assay). It inhibits increases in vascular permeability stimulated by substance P (Cay-24035) in a concentration-dependent manner in isolated guinea pig trachea and main bronchi. Vapreotide (8 nmol per animal) reduces substance P-induced biting and scratching in mice. It increases reaction time to heat stimuli in the hot plate and tail flick tests when administered at a dose of 512 µg/kg, indicating antinociceptive activity in mice. Vapreotide reduces plasma growth hormone (GH) increases induced by phenobarbital (Cay-9001494, Cay-20987), morphine (Cay-ISO60147), and chlorpromazine (Cay-16129), hypoglycemia-induced glucagon elevation, and glucose-induced insulin secretion in rats. It also decreases tumor weight and volume in a hamster model of pancreatic ductal adenocarcinoma and suppresses tumor growth and reduces GH secretion in SK-ES-1 and MNNG/HOS osteosarcoma mouse xenograft models.Formal Name: D-phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-tryptophanamide, cyclic (2->7)-disulfide, trifluoroacetate salt. Synonyms: BMY 41606, Octastatin, RC 160. Molecular Formula: C57H70N12O9S2 . XCF3COOH. Formula Weight: 1131.4. Purity: >95%. Formulation: (Request formulation change), A lyophilized powder. Solubility: Water: 1 mg/ml. SMILES: O=C(N[C@@H](C(C)C)C(N[C@H](C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N)=O)=O)CSSC[C@H](NC([C@H](N)CC3=CC=CC=C3)=O)C4=O)=O)[C@H](CCCCN)NC([C@@H](CC5=CNC6=C5C=CC=C6)NC([C@@](CC7=CC=C(O)C=C7)([H])N4)=O)=O.FC(F)(C(O)=O)F. InChi Code: InChI=1S/C57H70N12O9S2.C2HF3O2/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)18-10-11-23-58,3-2(4,5)1(6)7/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),(H,6,7)/t40-,43+,44+,45+,46-,47+,48+,49+,/m1./s1. InChi Key: LVZIATZDHWYHID-NCACADTJSA-N.