LINTITRIPT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H14ClN3O3S
Molecular Weight	411.861
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CN1C(=CC2=C1C=CC=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4Cl

InChI

InChIKey=ILNRQFBVVQUOLP-UHFFFAOYSA-N

InChI=1S/C20H14ClN3O3S/c21-14-7-3-2-6-13(14)15-11-28-20(22-15)23-19(27)17-9-12-5-1-4-8-16(12)24(17)10-18(25)26/h1-9,11H,10H2,(H,25,26)(H,22,23,27)

HIDE SMILES / InChI

Molecular Formula	C20H14ClN3O3S
Molecular Weight	411.861
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681406 | https://www.ncbi.nlm.nih.gov/pubmed/12229975

Lintitript (SR 27897) is a selective cholecystokinin type A (CCK-A) receptor antagonist, which was initially developed by Sanofi for appetite disorders. It is known, that CCK modulates feeding and dopamine-induced behavior in the central and peripheral nervous system. Lintitript presumably alters feeding habits, however, the exact mechanism of action is not known. Lintitript was investigated in animals with anorexia nervosa, in addition, drug was in clinical trial for the patients with advanced pancreatic cancer, but these studies were discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cholecystokinin receptor type A 2 Target ID: P32238 Gene ID: 886.0 Gene Symbol: CCKAR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10594328	Antagonist 2849		0.2 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced pancreatic cancer 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12229975	Primary		Phase II 1147	Unknown Approved Use Unknown
Anorexia 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24385417	Primary		Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466345	inconclusive [IC50 38.9018 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466345	no [IC50 24.5454 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206134	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466345	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346984#sid=144206134	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144206134	no

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00129Z	https://www.1pchem.com/search?query=1P00129Z
ApexBio Technology	B6965	https://www.apexbt.com/catalogsearch/result/?q=B6965
Axon MedChem	1245	https://www.axonmedchem.com/product/1245
BOC Sciences	136381-85-6	http://www.bocsci.com/description.asp?cas=136381-85-6
Chem Scene	CS-0021860	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0021860
eMolecules	6843913	https://orderbb.emolecules.com/search/#?query=6843913
mcule	MCULE-3638154542	https://mcule.com/MCULE-3638154542/
MedChem Express	HY-101764	https://www.medchemexpress.com/search.html?q=HY-101764&ft=&fa=&fp=
MolPort	MolPort-006-170-010	https://www.molport.com/shop/molecule-link/MolPort-006-170-010
MuseChem	I007674	https://www.musechem.com/product/I007674.html
Princeton BioMolecular Research	PBMR221963	http://www.princetonbio.com/order_online?common_id=PBMR221963
Tocris	2190	https://www.tocris.com/search.php?Type=QuickSearch&Value=2190
Wonderchem	WD054WN	http://www.wonder-chem.com/search.html?text=WD054WN

PubMed

Title	Date	PubMed
Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol.	2014-04	24385417
The agonist SR 146131 and the antagonist SR 27897 occupy different sites on the human CCK(1) receptor.	2000-07-21	10988332
Effect of lintitript, a new CCK-A receptor antagonist, on gastric emptying of a solid-liquid meal in humans.	1998-06-30	9712175
Peripheral biological activity of SR 27897: a new potent non-peptide antagonist of CCKA receptors.	1993-02-23	7681406

Patents

Sample Use Guides

In Vivo Use Guide

pancreatic cancer: nineteen patients were enrolled on a 28-day course of SR 27897B (lintitript). Initially, 4 patients received 20 mg of SR 27897B; 9 patients received 40 mg; and 6 patients 80 mg. Imaging studies, including FDG-PET and MRI, were performed at baseline and on days 14 and 28.

Route of Administration: Oral

In Vitro Use Guide

SR 27897 (lintitript) is a potent ligand for CCKA binding sites (rat pancreatic membranes, Ki = 0.2 nM) and is highly selective (CCKB and gastrin/CCKA IC50 ratios of 800 and 5000 respectively). In vitro, it is a competitive antagonist of cholecystokinin (CCK)-stimulated amylase release in isolated rat pancreatic acini (pA2 = 7.50) and of CCK-induced guinea pig gall bladder contractions (pA2 = 9.57).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:04 GMT 2025`
Record UNII	3YFV00531K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SR-27897

Preferred Name

English

LINTITRIPT

Official Name

English

2-((4-(O-CHLOROPHENYL)-2-THIAZOLYL)CARBAMOYL)INDOLE-1-ACETIC ACID

Common Name

English

lintitript [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C547