SINCALIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C49H62N10O16S3
Molecular Weight	1143.269
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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](CC2=CNC3=C2C=CC=C3)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC4=CC=CC=C4)C(N)=O

InChI

InChIKey=IZTQOLKUZKXIRV-YRVFCXMDSA-N

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

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=2331 | https://www.ncbi.nlm.nih.gov/pubmed/11159891

Sincalide is a synthetically-prepared C-terminal octapeptide of naturally occurring hormone cholecystokinin. Sincalide causes gallbladder contraction and stimulates secretion of pancreatic enzymes, and this property of the drug is used in diagnostic purposes. It is discussed that the drug acts by binding and stimulating the CCK-A receptor which is expressed in the target tissues. FDA approved sincalide under the name KINEVAC.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cholecystokinin A receptor 7 Target ID: CHEMBL1901 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11159891	Agonist 2678		1.4 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gallbladder disease 13 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d7f3d501-a389-4fe1-b20a-c9665b3f3d37	Diagnostic		Approved 8429	KINEVAC Approved Use Kinevac (Sincalide for Injection) may be used: (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. Launch Date 1976
Pancreas disorders 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d7f3d501-a389-4fe1-b20a-c9665b3f3d37	Diagnostic		Approved 8429	KINEVAC Approved Use Kinevac (Sincalide for Injection) may be used: (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. Launch Date 1976

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.3 min REVIEW https://www.wellrx.com/kinevac/monographs/	0.04 μg/kg bw single, intravenous dose: 0.04 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		SINCALIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0533	http://www.3bsc.com/index/pro_info.php?id=19889
AA Blocks	AA002QHZ	https://www.aablocks.com/goods/Goods/detail?id=AA002QHZ
AHH Chemical co.,ltd	API-1505	http://www.ahhchemical.com/product/API-1505.html
AK Scientific, Inc. (AKSCI)	O411	http://www.aksci.com/item_detail.php?cat=O411
Aaron Chemicals	AR002R9R	http://www.aaronchem.com/25126-32-3
Acorn PharmaTech	ACN-053730	http://www.acornpharmatech.com/
Alfa Chemistry	AP25126323	https://reagents.alfa-chemistry.com/product/tyr-so3h-27-cholecystokinin-fragment-26-cas-25126-32-3-8641.html
Ambinter	Amb19893461	http://www.ambinter.com/reference/19893461
Aurora Fine Chemicals LLC	A18.033.162	http://online.aurorafinechemicals.com/info?ID=A18.033.162
BOC Sciences	25126-32-3	https://www.bocsci.com/sincalide-kinevac-cas-25126-32-3-item-64129.html
Chem Scene	CS-5963	http://www.chemscene.com/25126-32-3.html
ChemShuttle	141332	http://www.chemshuttle.com/catalogsearch/result/?q=25126-32-3&cat=
Chemenu	CM100979	http://www.chemenu.com/products/CM100979
Chemspace	CSSB00161190236	https://chem-space.com/CSSB00161190236
DC Chemicals	DC22525	http://www.dcchemicals.com/product_show-DC22525.html
Glentham Life Sciences	GL1683	http://www.glentham.com/products/product/GL1683/
MedChem Express	HY-P0093	https://www.medchemexpress.com/Sincalide.html
MolPort	MolPort-006-124-517	https://www.molport.com/shop/molecule-link/MolPort-006-124-517
MuseChem	I002853	https://www.musechem.com/product/I002853.html
OChem	5121	http://www.ocheminc.com/index.php?act=psearch&pid=126S323
Shanghai Hanhong Scientific	90P01	http://www.hanhonggroup.com/data/products_en/90P01.html
Smolecule	S543220	http://www.smolecule.com/products/s543220
THE BioTek	bt-283327	https://www.thebiotek.com/product/inhibitors/bt-283327
Tocris	1166	https://www.tocris.com/products/cck-octapeptide-sulfated_1166
abcr GmbH	AB504314	http://www.abcr.de/shop/en/AB504314
eNovation Chemicals	D663492	https://www.enovationchem.com/ProductDetails.asp?ProductID=D663492

PubMed

Title	Date	PubMed
Structure-activity and dose-effect relationships of the antagonism of picrotoxin-induced seizures by cholecystokinin, fragments and analogues of cholecystokinin in mice.	1983 Oct	6316193
Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity.	1990 Sep	1975695
The human brain cholecystokinin-B/gastrin receptor. Cloning and characterization.	1993 Apr 15	7681836
Functional characterization of a human brain cholecystokinin-B receptor. A trophic effect of cholecystokinin and gastrin.	1993 Aug 25	8349705
The in vivo metabolism of cholecystokinin (CCK-8) is essentially ensured by aminopeptidase A.	1996	8804068
Identification of metabolic pathways of brain angiotensin II and III using specific aminopeptidase inhibitors: predominant role of angiotensin III in the control of vasopressin release.	1996 Oct 15	8876246
Vectorial transport of the peptide CCK-8 by double-transfected MDCKII cells stably expressing the organic anion transporter OATP1B3 (OATP8) and the export pump ABCC2.	2005 May	15665139
Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells.	2005 Oct	16046661
Mechanisms of oleoylethanolamide-induced changes in feeding behavior and motor activity.	2005 Sep	15879057
Enzymatic properties of human aminopeptidase A. Regulation of its enzymatic activity by calcium and angiotensin IV.	2006 Aug 18	16790432
Cloning/characterization of the canine organic anion transporting polypeptide 1b4 (Oatp1b4) and classification of the canine OATP/SLCO members.	2010 Apr	20079461
Interaction of the bioactive flavonol, icariin, with the essential human solute carrier transporters.	2014 Feb	24265111
Cholecystokinin-octapeptide restored morphine-induced hippocampal long-term potentiation impairment in rats.	2014 Jan 24	24309294

Sample Use Guides

In Vivo Use Guide

For prompt contraction of the gallbladder, a dose of 0.02 mcg sincalide per kg (1.4 mcg/70 kg) is injected intravenously over a 30- to 60-second interval. For the test of pancreatic function, the patient receives a dose of 0.25 units secretin per kg by intravenous infusion over a 60-minute period. Thirty minutes after the initiation of the secretin infusion, a separate IV infusion of sincalide at a total dose of 0.02 mcg per kg is administered over a 30-minute interval. To accelerate the transit time of a barium meal through the small bowel, the drug should be given at a dose of 0.04 mcg sincalide per kg (2.8 mcg/70 kg) injected intravenously over a 30- to 60- second interval.

Route of Administration: Intravenous

In Vitro Use Guide

Muscle cells of gallbladders were exposed to sincalide (10(-7)-10(-13) M) for 30 sec to induce cells contraction.

Name

Type

Language

SINCALIDE

Official Name

English

CCK C-TERMINAL OCTAPEPTIDE

Common Name

English

Sincalide [WHO-DD]

Common Name

English

CAERULEIN, 1-DE(5-OXO-L-PROLINE)-2-DE-L-GLUTAMINE-5-L-METHIONINE-

Common Name

English

CHOLECYSTOKININ C-TERMINAL OCTAPEPTIDE

Common Name

English

L-ASPARTYL-L-TYROSYL-L-METHIONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ASPARTYLPHENYL-L-ALANINAMIDE HYDROGEN SULFATE (ESTER)

Common Name

English

KINEVAC

Brand Name

English

L-.ALPHA.-ASPARTYL-O-SULFO-L-TYROSYL-L-METHIONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE

Common Name

English

SQ 19844

Code

English

SINCALIDE [USP IMPURITY]

Common Name

English

SINCALIDE [USAN]

Common Name

English

SINCALIDE [MI]

Common Name

English

SINCALIDE [MART.]

Common Name

English

SINCALIDE [VANDF]

Common Name

English

sincalide [INN]

Common Name

English

SINCALIDE [ORANGE BOOK]

Common Name

English

CHOLECYSTOKININ C-TERMINAL OCTAPEPTIDE [MI]

Common Name

English

SQ-19844

Code

English

CCK-8s

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175798