Sincalide
Identification
- Summary
Sincalide is a diagnostic agent used to stimulate gallbladder contraction or pancreatic secretion during diagnostic tests, and accelerate fluoroscopy and x-ray examination of the intestinal tract.
- Brand Names
- Kinevac
- Generic Name
- Sincalide
- DrugBank Accession Number
- DB09142
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sincalide (DB09142)
- Weight
- Average: 1143.27
Monoisotopic: 1142.350739478 - Chemical Formula
- C49H62N10O16S3
- Synonyms
- CCK C-terminal octapeptide
- CCK-8
- Cholecystokinin C-terminal octapeptide
- Sincalide
- External IDs
- SQ 19844
- SQ-19844
- SQ19844
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.
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- Contraindications & Blackbox Warnings
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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.
- 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
- Adverse Effects
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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 Integrate drug-drug
interactions in your softwareAsunaprevir 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. Bempedoic acid The excretion of Sincalide can be decreased when combined with Bempedoic acid. Cabazitaxel The excretion of Sincalide can be decreased when combined with Cabazitaxel. Clarithromycin The excretion of Sincalide can be decreased when combined with Clarithromycin. Cobicistat The excretion of Sincalide can be decreased when combined with Cobicistat. Cobimetinib The excretion of Sincalide can be decreased when combined with Cobimetinib. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Kinevac Powder, for solution 5 mcg / vial Intravenous Bracco Imaging S.P.A. 1998-07-08 Not applicable Canada 
Kinevac Injection, powder, lyophilized, for solution 5 ug/5mL Intravenous General Injectables & Vaccines 2010-11-05 2017-01-17 US 
Kinevac Injection, powder, lyophilized, for solution 5 ug/5mL Intravenous Bracco Diagnostics Inc. 1976-07-21 Not applicable US Kinevac Injection, powder, lyophilized, for solution 5 ug/5mL Intravenous Jubilant Hollisterstier Llc 2007-09-05 2018-02-01 US Kinevac Pws Inj 5mcg/vial Powder, for solution 5 mcg / vial Intravenous Squibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc. 1979-12-31 1998-07-30 Canada SIncalide Injection, powder, lyophilized, for solution 3 ug/1 Intravenous Anazao Health Corporation 2012-06-19 Not applicable US Sincalide for Injection Powder, for solution 5 mcg / vial Intravenous Avir Pharma Inc Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image SIncalide Sincalide (3 ug/1) Injection, powder, lyophilized, for solution Intravenous Anazao Health Corporation 2012-06-19 Not applicable US
Categories
- ATC Codes
- V04CC03 — Sincalide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alkylindole / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Arylsulfate show 43 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- M03GIQ7Z6P
- CAS number
- 25126-32-3
- 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
References
- General References
- FDA Approved Drug Products: KINEVAC (sincalide) injection [Link]
- External Links
- KEGG Drug
- D05845
- PubChem Compound
- 9833444
- PubChem Substance
- 310265055
- ChemSpider
- 8009168
- BindingDB
- 21147
- 9800
- ChEBI
- 135946
- ChEMBL
- CHEMBL1121
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sincalide
- FDA label
- Download (1.5 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Type 2 Diabetes Mellitus 1 3 Completed Other Healthy Subjects (HS) 1 1 Not Yet Recruiting Treatment Healthy Subjects (HS) 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 / vial Injection, powder, lyophilized, for solution Intravenous 3 ug/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6803046 No 2004-10-12 2022-08-16 US
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
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
- 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. [Article]
Drug created on September 30, 2015 18:56 / Updated on October 24, 2021 16:00