Caerulein (Ceruletide, Cerulein, FI-6934) is a cholecystokinin (CCK) receptor agonist, a safe and effective gallbladder metabolic drug, and an exocrine stimulant in the small intestine and pancreas.

 

Brand: BCM

 

Target: cholecystokinin

 

Signaling Pathways: GPCR/G Protein

 

In Vitro: Ceruletide is the same as biologically and chemically to the human gastrointestinal hormones cholecystokinin-pancreozymin (CCK) and gastrin II. Ceruletide stimulates gallbladder contraction while delaying gastric emptying and inhibiting motility in the proximal duodenum. Ceruletide in supramaximal but not in physiological doses activate NF-kappaB/Rel in vitro. This activation may induce a self-defending genetic program before the onset of cellular injury and may prevent higher degrees of damage of pancreatic acinar cells after secretagogue hyperstimulation.

 

Melting Point: 224-226° (dec)

 

Specific Rotation: D20 -26° (c = 1 in DMF)

 

Solubility: Soluble in DMSo. Insoluble in Water; insoluble in Ethanol.

 

Isomeric SMILES: C[C@H]([C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O  

 

InChIKey: YRALAIOMGQZKOW-HYAOXDFASA-N  

 

InChI: InChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1

 

Attribute
[Chem Name]	(3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
[Synonym]	Caerulein; FI-6934; Ceruletide
[CAS No.]	17650-98-5
[MDL No.]	MFCD00076478
[Formula]	C58H73N13O21S2
[Molecular]	1352.4
[Form]	White to Off-White Solid
[Storage]	Sealed in dry. Store in freezer, under -20°C

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