Ceruletide

Ceruletide is a decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction. It has a role as a diagnostic agent and a gastrointestinal drug.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Ceruletide(CAS 17650-98-5)

CAT No: C03003

CAS No:17650-98-5

Synonyms/Alias:Caerulein;Ceruletide;17650-98-5;Cerulein;Ceruletida;Ceruletidum;Ceruletidum [INN-Latin];Ceruletida [INN-Spanish];Ceruletide [USAN:INN:BAN];CCRIS 3063;5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide;CHEBI:59219;CERULETIDE [MI];CERULETIDE [INN];CERULETIDE [USAN];5-Oxo-L-prolyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide 4-(hydrogen sulfate) (ester);CERULETIDE [MART.];CERULETIDE [WHO-DD];888Y08971B;DTXSID8040434;Caerulein (~85%);Ceruletidum (INN-Latin);Ceruletida (INN-Spanish);CERULETIDE (MART.);(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid;pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2;Ceruletid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE;5-oxo-L-prolyl-L-glutaminyl-L-a-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-a-aspartyl-L-phenylalaninamide;Ceruletide (USAN/INN);UNII-888Y08971B;(3S)-3-(((1S)-1-carbamoyl-2-phenylethyl)carbamoyl)-3-((2S)-2-((2S)-2-(2-((2S,3R)-2-((2S)-2-((2S)-2-((2S)-4-carbamoyl-2-(((2S)-5-oxopyrrolidin-2-yl)formamido)butanamido)-3-carboxypropanamido)-3-(4-(sulfooxy)phenyl)propanamido)-3-hydroxybutanamido)acetamido)-3-(1H-indol-3-yl)propanamido)-4-(methylsulfanyl)butanamido)propanoic acid;Caerulein, sulfated;Caerulein triammonium;MFCD00076478;ceruletide diethylamide;Ceruletide (Standard);SCHEMBL29520;GTPL7589;CHEMBL1201355;DTXCID6020434;HY-A0190R;V04CC04;YRALAIOMGQZKOW-HYAOXDFASA-N;HY-A0190;AKOS030529560;CS-5876;DB00403;AS-56061;FC108931;NS00004791;C73362;D03442;EN300-23248418;Q5065299;(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ALPHA-ASPARTYL-L-PHENYLALANINAMIDE;

Chemical 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

Custom Peptide Synthesis
cGMP Peptide
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  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C58H73N13O21S2
M.W/Mr.
1352.4
Sequence
One Letter Code:XQDXTGWMDF
Three Letter Code:H-Pyr-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
Activity
Agonist
Biological Activity
CCK agonist. Stimulates biosynthesis of pancreatic enzymes in AR4-2J pancreatic cells in vitro. Induces acute pancreatitis in mice. Also enhances proteasome activity in Gdeg mice.
Target
CCK receptor
Long-term Storage Conditions
Soluble to 1 mg/ml in water
Shipping Condition
Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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
InChI Key
YRALAIOMGQZKOW-HYAOXDFASA-N
Canonical SMILES
CC(C(C(=O)NCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C5CCC(=O)N5)O
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

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