Sincalide is a medication given by injection to assist in the diagnosis of gallbladder and pancreas disorders. It is identified as the 8-amino acid C-terminal segment of cholecystokinin and is also known as CCK-8. Naturally occurring cholecystokinin is a gastrointestinal peptide hormone normally essential for stimulating protein and fat digestion in the body. When injected intravenously, sincalide produces a substantial reduction in gallbladder size by causing this organ to contract. The evacuation of bile that results is similar to that which occurs physiologically in response to endogenous cholecystokinin. Furthermore, sincalide stimulates pancreatic secretion of bicarbonate and enzymes.

As the product Kinevac (FDA), sincalide is used for the following indications: 1) to stimulate gallbladder contraction, as may be assessed by various methods of diagnostic imaging, or to obtain by duodenal aspiration a sample of concentrated bile for analysis of cholesterol, bile salts, phospholipids, and crystals; (2) to stimulate pancreatic secretion (especially in conjunction with secretin) prior to obtaining a duodenal aspirate for analysis of enzyme activity, composition, and cytology; (3) to accelerate the transit of a barium meal through the small bowel, thereby decreasing the time and extent of radiation associated with fluoroscopy and x-ray examination of the intestinal tract.

Structure

Similar Structures

Synonyms

CCK C-terminal octapeptide
CCK-8
Cholecystokinin C-terminal octapeptide
Sincalide

External IDs

SQ 19844 / SQ-19844 / SQ19844

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Kinevac	Injection, powder, lyophilized, for solution	5 ug/5mL	Intravenous	General Injectables & Vaccines	2010-11-05	2017-01-17
Kinevac	Powder, for solution	5 mcg	Intravenous	Bracco Imaging S.P.A.	1998-07-08	Not applicable
Kinevac	Injection, powder, lyophilized, for solution	5 ug/5mL	Intravenous	Bracco Diagnostics Inc.	1976-07-21	Not applicable
Kinevac	Injection, powder, lyophilized, for solution	5 ug/5mL	Intravenous	Jubilant Hollisterstier Llc	2007-09-05	2018-02-01
Kinevac Pws Inj 5mcg/vial	Powder, for solution		Intravenous	Squibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.	1979-12-31	1998-07-30
SIncalide	Injection, powder, lyophilized, for solution	3 ug/1	Intravenous	Anazao Health Corporation	2012-06-19	Not applicable
Sincalide for Injection	Powder, for solution		Intravenous	Avir Pharma Inc	Not applicable	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
SIncalide	Sincalide (3 ug/1)	Injection, powder, lyophilized, for solution	Intravenous	Anazao Health Corporation	2012-06-19	Not applicable

Categories

UNII

M03GIQ7Z6P

CAS number

25126-32-3

Weight

Average: 1143.27
Monoisotopic: 1142.350739478

Chemical Formula

C₄₉H₆₂N₁₀O₁₆S₃

InChI Key

IZTQOLKUZKXIRV-YRVFCXMDSA-N

InChI

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

IUPAC Name

(3S)-3-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid

SMILES

CSCC[C@H](NC(=O)[C@H](CC1=CC=C(OS(O)(=O)=O)C=C1)NC(=O)[C@@H](N)CC(O)=O)C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O

Pharmacology

Indication

Associated Therapies

Pharmacodynamics

Not Available

Mechanism of action

When injected intravenously, sincalide produces a substantial reduction in gallbladder size by causing this organ to contract. The evacuation of bile that results is similar to that which occurs physiologically in response to endogenous cholecystokinin. Like cholecystokinin, sincalide stimulates pancreatic secretion; concurrent administration with secretin increases both the volume of pancreatic secretion and the output of bicarbonate and protein (enzymes) by the gland. This combined effect of secretin and sincalide permits the assessment of specific pancreatic function through measurement and analysis of the duodenal aspirate.

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The intravenous (bolus) administration of sincalide causes a prompt contraction of the gallbladder that becomes maximal in 5 to 15 minutes, as compared with the stimulus of a fatty meal which causes a progressive contraction that becomes maximal after approximately 40 minutes.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Asunaprevir	The excretion of Sincalide can be decreased when combined with Asunaprevir.
Ataluren	The excretion of Sincalide can be decreased when combined with Ataluren.
Atazanavir	The excretion of Sincalide can be decreased when combined with Atazanavir.
Baricitinib	The excretion of Sincalide can be decreased when combined with Baricitinib.
Beclomethasone dipropionate	The excretion of Sincalide can be decreased when combined with Beclomethasone dipropionate.
Cabazitaxel	The excretion of Sincalide can be decreased when combined with Cabazitaxel.
Cobicistat	The excretion of Sincalide can be decreased when combined with Cobicistat.
Cobimetinib	The excretion of Sincalide can be decreased when combined with Cobimetinib.
Cyclosporine	The excretion of Sincalide can be decreased when combined with Cyclosporine.
Dabrafenib	The excretion of Sincalide can be decreased when combined with Dabrafenib.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

General References

Not Available

External Links

KEGG Drug: D05845
PubChem Compound: 9833444
PubChem Substance: 310265055
ChemSpider: 8009168
BindingDB: 21147
RxNav: 9800
ChEBI: 135946
ChEMBL: CHEMBL1121
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Sincalide

ATC Codes

V04CC03 — Sincalide

AHFS Codes

36:34.00 — Gallbladder Function

FDA label

Download (1.5 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Type 2 Diabetes Mellitus	1
Not Available	Completed	Other	Healthy Volunteers	1
Not Available	Completed	Treatment	Cholestasis	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Injection, powder, lyophilized, for solution	Intravenous	5 ug/5mL
Powder, for solution	Intravenous	5 mcg
Powder, for solution	Intravenous
Injection, powder, lyophilized, for solution	Intravenous	3 ug/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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US6803046	No	2004-10-12	2022-08-16

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00441 mg/mL	ALOGPS
logP	0.48	ALOGPS
logP	-2.4	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	426.8 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	282.07 m³·mol^-1	ChemAxon
Polarizability	112.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom: Organic compounds
Super Class: Organic acids and derivatives
Class: Carboxylic acids and derivatives
Sub Class: Amino acids, peptides, and analogues
Direct Parent: Oligopeptides
Alternative Parents: Phenylalanine and derivatives / Aspartic acid and derivatives / Methionine and derivatives / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / Alpha amino acid amides / Phenylsulfates / Amphetamines and derivatives / 3-alkylindoles / Phenoxy compounds
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Substituents: Alpha-oligopeptide / Phenylalanine or derivatives / Methionine or derivatives / Aspartic acid or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Triptan / Phenylsulfate / N-substituted-alpha-amino acid / Arylsulfate
show 43 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: Not Available

Transporters

Details1. Solute carrier organic anion transporter family member 1B3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name: SLCO1B3
Uniprot ID: Q9NPD5
Uniprot Name: Solute carrier organic anion transporter family member 1B3
Molecular Weight: 77402.175 Da

References

Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Drug created on September 30, 2015 12:56 / Updated on February 25, 2020 00:19

Sincalide

Identification

Structure for Sincalide (DB09142)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Transporters

References