U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of SINCALIDE

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
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

Sources: www.ncbi.nlm.nih.gov/pubmed/5344529

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.4 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
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
Diagnostic
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 min
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells.
2005 Oct
Mechanisms of oleoylethanolamide-induced changes in feeding behavior and motor activity.
2005 Sep
Enzymatic properties of human aminopeptidase A. Regulation of its enzymatic activity by calcium and angiotensin IV.
2006 Aug 18

Sample Use Guides

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
Muscle cells of gallbladders were exposed to sincalide (10(-7)-10(-13) M) for 30 sec to induce cells contraction.
Name Type Language
SINCALIDE
INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
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
MI  
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
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
NDF-RT N0000007750
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
NDF-RT N0000007750
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
WHO-ATC V04CC03
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
NCI_THESAURUS C1937
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
NDF-RT N0000007750
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
WHO-VATC QV04CC03
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
Code System Code Type Description
SMS_ID
100000083517
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY
LACTMED
Sincalide
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PRIMARY
INN
3617
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PRIMARY
FDA UNII
M03GIQ7Z6P
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PRIMARY
EVMPD
SUB10531MIG
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PRIMARY
MESH
D012844
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PRIMARY
EPA CompTox
DTXSID7048617
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PRIMARY
CAS
25126-32-3
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PRIMARY
DAILYMED
M03GIQ7Z6P
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY
DRUG CENTRAL
4627
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PRIMARY
RXCUI
9800
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PRIMARY RxNorm
MERCK INDEX
m9951
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C47719
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PRIMARY
PUBCHEM
9833444
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PRIMARY
DRUG BANK
DB09142
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY
ECHA (EC/EINECS)
246-639-0
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY
WIKIPEDIA
SINCALIDE
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY
ChEMBL
CHEMBL1121
Created by admin on Fri Dec 15 15:47:40 GMT 2023 , Edited by admin on Fri Dec 15 15:47:40 GMT 2023
PRIMARY