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Merck
CN

21026

Caerulein

≥97.0% (HPLC)

Synonym(s):

Caerulein Sulfated, Cerulein, Ceruletide, [Tyr(SO3H)4]Caerulein, pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2

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About This Item

Empirical Formula (Hill Notation):
C58H73N13O21S2
CAS Number:
17650-98-5
Molecular Weight:
1352.40
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
5422487
MDL number:
MFCD00076478

Key Documents

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InChI key

YRALAIOMGQZKOW-HJMGKOKZSA-N

SMILES string

CSCC[C@H](NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)CNC(=O)C(NC(=O)[C@H](Cc3ccc(OS(O)(=O)=O)cc3)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H]4CCC(=O)N4)[C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](Cc5ccccc5)C(N)=O

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

assay

≥80% peptide basis, ≥97.0% (HPLC)

solubility

0.05 M ammonium hydroxide: 1 mg/mL, clear, colorless

storage temp.

−20°C

Biochem/physiol Actions

Effects on perception of pain are conflicting. It prevents gall bladder pain, renal colic, and the pain of intermittent claudication; however, in general, it is seen as an antagonist of endogenous opioids.

Other Notes

A cholecystokinin analog. Review; In studies on protease zymogens

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Active polypeptides of nonmammalian origin.
G Bertaccini
Pharmacological reviews, 28(2), 127-177 (1976-06-01)
W Steinhilber et al.
Proceedings of the National Academy of Sciences of the United States of America, 85(18), 6597-6601 (1988-09-01)
Infusion of rats with optimal doses of caerulein for up to 24 hr resulted in divergent changes in protein synthesis in the exocrine pancreas: a 3-fold increase in synthesis of anionic trypsinogen and a 75% decrease in synthesis of amylase.
Dinesh Srinivasan et al.
Biochimie, 95(2), 429-435 (2012-11-13)
Peptidomic analysis of norepinephrine-stimulated skin secretions of the tetraploid clawed frog Xenopus laevis (Pipidae) led to the identification of 10 peptides with the ability to stimulate the release of insulin from the rat BRIN-BD11 clonal β cell line. These peptides
Christoph B Westphalen et al.
Methods in molecular biology (Clifton, N.J.), 980, 291-300 (2013-01-30)
Pancreatic cancer is a uniformly lethal disease characterized by a strong stromal reaction called desmoplasia. Organ fibrosis is also a feature of chronic pancreatitis a known risk factor for pancreatic cancer. Here we describe a transplantation approach to investigate bone
Jie Xiong et al.
Journal of ethnopharmacology, 145(2), 573-580 (2012-12-04)
Shikonin, a highly liposoluble naphthoquinone pigment isolated from the traditional medical herbs Lithospermum erythrorhizon (LE), was considered to exhibit an anti-inflammatory property. While the potential of shikonin to ameliorate acute pancreatitis (AP) is unknown. Our aim was to investigate the
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