Identification

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Name
Sincalide
Accession Number
DB09142
Type
Small Molecule
Groups
Approved
Description

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
Thumb
Synonyms
  • CCK C-terminal octapeptide
  • CCK-8
  • Cholecystokinin C-terminal octapeptide
  • Sincalide
External IDs
SQ 19844 / SQ-19844 / SQ19844
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
KinevacInjection, powder, lyophilized, for solution5 ug/5mLIntravenousGeneral Injectables & Vaccines2010-11-052017-01-17Us
KinevacInjection, powder, lyophilized, for solution5 ug/5mLIntravenousBracco Diagnostics Inc.1976-07-21Not applicableUs
KinevacInjection, powder, lyophilized, for solution5 ug/5mLIntravenousJubilant Hollisterstier Llc2007-09-052018-02-01Us
Kinevac (sincalide) for Injection 5mcg/vialPowder, for solution5 mcgIntravenousBracco Imaging S.P.A.1998-07-08Not applicableCanada
Kinevac Pws Inj 5mcg/vialPowder, for solution5 mcgIntravenousSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.1979-12-311998-07-30Canada
SIncalideInjection, powder, lyophilized, for solution3 ug/1IntravenousAnazao Health Corporation2012-06-19Not applicableUs
Additional Data Available
  • Application Number
    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
    Product Code

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

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SIncalideSincalide (3 ug/1)Injection, powder, lyophilized, for solutionIntravenousAnazao Health Corporation2012-06-19Not applicableUs
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

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.

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.

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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Additional Data Available
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
DrugInteraction
AsunaprevirThe excretion of Sincalide can be decreased when combined with Asunaprevir.
AtalurenThe excretion of Sincalide can be decreased when combined with Ataluren.
AtazanavirThe excretion of Sincalide can be decreased when combined with Atazanavir.
BaricitinibThe excretion of Sincalide can be decreased when combined with Baricitinib.
CabazitaxelThe excretion of Sincalide can be decreased when combined with Cabazitaxel.
CiclosporinThe excretion of Sincalide can be decreased when combined with Ciclosporin.
ClotrimazoleThe excretion of Sincalide can be increased when combined with Clotrimazole.
CobicistatThe excretion of Sincalide can be decreased when combined with Cobicistat.
CobimetinibThe excretion of Sincalide can be decreased when combined with Cobimetinib.
DabrafenibThe excretion of Sincalide can be decreased when combined with Dabrafenib.
Additional Data Available
  • Extended Description
    Extended Description

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

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  • Severity
    Severity

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

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  • Evidence Level
    Evidence Level

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

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  • Action
    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
ChEBI
135946
ChEMBL
CHEMBL1121
Wikipedia
Sincalide
ATC Codes
V04CC03 — Sincalide
AHFS Codes
  • 36:34.00 — Gallbladder Function
FDA label
Download (1.5 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableCompletedOtherHealthy Volunteers1
Not AvailableCompletedTreatmentCholestasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous5 ug/5mL
Powder, for solutionIntravenous5 mcg
Injection, powder, lyophilized, for solutionIntravenous3 ug/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6803046No2004-10-122022-08-16Us
Additional Data Available
  • Filed On
    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
PropertyValueSource
Water Solubility0.00441 mg/mLALOGPS
logP0.48ALOGPS
logP-2.4ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area426.8 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity282.07 m3·mol-1ChemAxon
Polarizability112.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
show 17 more
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

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
  1. 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 June 18, 2019 01:48