Sincalide
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MedKoo CAT#: 328331

CAS#: 25126-32-3

Description: Sincalide, also known as CCK-8, is a drug used to treat cholecystitis. Sincalide is an octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.

Chemical Structure

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Sincalide
CAS# 25126-32-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 328331
Name: Sincalide
CAS#: 25126-32-3
Chemical Formula: C49H62N10O16S3
Exact Mass: 1,142.35
Molecular Weight: 1,143.270
Elemental Analysis: C, 51.48; H, 5.47; N, 12.25; O, 22.39; S, 8.41

Price and Availability

Size Price Availability Quantity
1mg USD 250
5mg USD 950 2 Weeks
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Synonym: Sincalide; CCK-8; CCK 8; CCK8; CCK-8S; CCK 8S; CCK8S; Kinevac

IUPAC/Chemical Name: (3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-amino-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosanedioic acid

InChi Key: IZTQOLKUZKXIRV-YRVFCXMDSA-N

InChi Code: InChI=1S/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35-,36-,37-,38-,39-/m0/s1

SMILES Code: O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CC(O)=O)NC([C@H](CCSC)NC([C@H](CC2=CNC3=C2C=CC=C3)NC(CNC([C@H](CCSC)NC([C@H](CC4=CC=C(OS(=O)(O)=O)C=C4)NC([C@H](CC(O)=O)N)=O)=O)=O)=O)=O)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMF and water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Sincalide can promote gallbladder contraction by injection and helps diagnose gallbladder and pancreas disorders. Sincalide can increase bile secretion, cause the gallbladder to contract and relax the sphincter of Oddi, resulting in bile drainage into the duodenum. Sincalide is a major bioactive segment of CCK that retains most of the biological activities of CCK.
In vitro activity: Sincalide protects H9c2 cardiomyoblasts from Ang II-induced apoptosis partly via activation of the CCK1 receptor and the phosphatidyqinositol-3 kinase/protein kinase B (PI3K/Akt) signaling pathway. Pretreatment of sincalide attenuated Ang II-induced cell toxicity and apoptosis, induced expression of p-Akt, p-bad, and Bcl-2, and decreased the expression levels of Bax and caspase-3. Reference: J Cell Biochem. 2020 Jul;121(7):3560-3569. https://pubmed.ncbi.nlm.nih.gov/31886572/
In vivo activity: Sincalide alleviated fibrosis in the noninfarcted regions and delayed the left ventricular remodeling and the progress of heart failure in a myocardial infarction rat model. Sincalide improved left ventricular function and attenuated myocardial fibrosis. Sincalide downregulated cardiac fibrosis genes in the left ventricle. Reference: Int J Biochem Cell Biol. 2020 Aug;125:105793. https://pubmed.ncbi.nlm.nih.gov/32554056/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 50.0 43.73
Water 50.0 43.73

Preparing Stock Solutions

The following data is based on the product molecular weight 1,143.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zhang WH, Zhang ML, Jing WW, Xie B, Bi HT, Yu F, Cong B, Ma CL, Wen D. Inhibitory Effect of CCK-8 on Methamphetamine-Induced Apoptosis. Fa Yi Xue Za Zhi. 2021 Dec 25;37(6):796-805. English, Chinese. doi: 10.12116/j.issn.1004-5619.2021.310206. PMID: 35243844. 2. Wang C, Yu H, Wei L, Zhang J, Hong M, Chen L, Dong X, Fu L. Protective effect of cholecystokinin octapeptide on angiotensin II-induced apoptosis in H9c2 cardiomyoblast cells. J Cell Biochem. 2020 Jul;121(7):3560-3569. doi: 10.1002/jcb.29639. Epub 2019 Dec 30. PMID: 31886572. 3. Wang C, Zhang C, Wu D, Guo L, Zhao F, Lv J, Fu L. Cholecystokinin octapeptide reduces myocardial fibrosis and improves cardiac remodeling in post myocardial infarction rats. Int J Biochem Cell Biol. 2020 Aug;125:105793. doi: 10.1016/j.biocel.2020.105793. Epub 2020 Jun 15. PMID: 32554056. 4. Plaza A, Merino B, Del Olmo N, Ruiz-Gayo M. The cholecystokinin receptor agonist, CCK-8, induces adiponectin production in rat white adipose tissue. Br J Pharmacol. 2019 Aug;176(15):2678-2690. doi: 10.1111/bph.14690. Epub 2019 Jun 20. PMID: 31012948; PMCID: PMC6609540.
In vitro protocol: 1. Zhang WH, Zhang ML, Jing WW, Xie B, Bi HT, Yu F, Cong B, Ma CL, Wen D. Inhibitory Effect of CCK-8 on Methamphetamine-Induced Apoptosis. Fa Yi Xue Za Zhi. 2021 Dec 25;37(6):796-805. English, Chinese. doi: 10.12116/j.issn.1004-5619.2021.310206. PMID: 35243844. 2. Wang C, Yu H, Wei L, Zhang J, Hong M, Chen L, Dong X, Fu L. Protective effect of cholecystokinin octapeptide on angiotensin II-induced apoptosis in H9c2 cardiomyoblast cells. J Cell Biochem. 2020 Jul;121(7):3560-3569. doi: 10.1002/jcb.29639. Epub 2019 Dec 30. PMID: 31886572.
In vivo protocol: 1. Wang C, Zhang C, Wu D, Guo L, Zhao F, Lv J, Fu L. Cholecystokinin octapeptide reduces myocardial fibrosis and improves cardiac remodeling in post myocardial infarction rats. Int J Biochem Cell Biol. 2020 Aug;125:105793. doi: 10.1016/j.biocel.2020.105793. Epub 2020 Jun 15. PMID: 32554056. 2. Plaza A, Merino B, Del Olmo N, Ruiz-Gayo M. The cholecystokinin receptor agonist, CCK-8, induces adiponectin production in rat white adipose tissue. Br J Pharmacol. 2019 Aug;176(15):2678-2690. doi: 10.1111/bph.14690. Epub 2019 Jun 20. PMID: 31012948; PMCID: PMC6609540.

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1: Covington MF, Krupinski E, Avery RJ, Kuo PH. Classification schema of symptomatic enterogastric reflux utilizing sincalide augmentation on hepatobiliary scintigraphy. J Nucl Med Technol. 2014 Sep;42(3):198-202. doi: 10.2967/jnmt.114.141168. Epub 2014 Jul 17. PubMed PMID: 25033884.

2: Norenberg JP, Ponto JA, Petry NA, Wittstrom KM. Commentary: Prescriber beware: it is ill advised to administer compounded sincalide. J Nucl Med. 2013 Nov;54(11):23N-4N. PubMed PMID: 24187044.

3: Ziessman H, Petry NA. Sincalide is temporarily unavailable--again. J Nucl Med. 2013 Aug;54(8):17N. PubMed PMID: 23908270.

4: Ziessman HA. Sincalide cholescintigraphy--32 years later: evidence-based data on its clinical utility and infusion methodology. Semin Nucl Med. 2012 Mar;42(2):79-83. doi: 10.1053/j.semnuclmed.2011.10.002. PubMed PMID: 22293163.

5: Irwin N, Pathak V, Flatt PR. A Novel CCK-8/GLP-1 Hybrid Peptide Exhibiting Prominent Insulinotropic, Glucose-Lowering, and Satiety Actions With Significant Therapeutic Potential in High-Fat-Fed Mice. Diabetes. 2015 Aug;64(8):2996-3009. doi: 10.2337/db15-0220. Epub 2015 Apr 16. PubMed PMID: 25883113.

6: Woodard J, Bencherif B, Clavell M, Joyce J. Dicyclomine: cause of abnormally decreased gall bladder ejection with sincalide-stimulated hepatobiliary scintigraphy. Clin Nucl Med. 2012 Jan;37(1):82-5. doi: 10.1097/RLU.0b013e3182291c7a. PubMed PMID: 22157036.

7: Kaczyńska K, Szereda-Przestaszewska M. Contribution of CCK1 receptors to cardiovascular and respiratory effects of cholecystokinin in anesthetized rats. Neuropeptides. 2015 Dec;54:29-34. doi: 10.1016/j.npep.2015.08.006. Epub 2015 Aug 19. PubMed PMID: 26342277.

8: Wang EM, Li WT, Yan XJ, Chen X, Liu Q, Feng CC, Cao ZJ, Fang JY, Chen SL. Vagal afferent-dependent cholecystokinin modulation of visceral pain requires central amygdala NMDA-NR2B receptors in rats. Neurogastroenterol Motil. 2015 Sep;27(9):1333-43. doi: 10.1111/nmo.12633. Epub 2015 Jul 22. PubMed PMID: 26197883.

9: Ziessman HA, Tulchinsky M, Maurer A. Consensus report on standardization of sincalide cholescintigraphy. J Nucl Med. 2011 Aug;52(8):16N. PubMed PMID: 21810583.

10: Fotos JS, Tulchinsky M. Oral Cholecystagogue Cholescintigraphy: A Systematic Review of Fatty Meal Options. Clin Nucl Med. 2015 Oct;40(10):796-8. doi: 10.1097/RLU.0000000000000913. Review. PubMed PMID: 26222535.