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=CC=CC=C12)C(=O)NC3=NC(=CS3)C4=C(Cl)C=CC=C4

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)

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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 2778		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 1132	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 1587 inducer 781	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466345	inconclusive [IC50 38.9018 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466345	no [IC50 24.5454 uM]
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206134	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466345	no
CYP3A4 1925	inducer 1573 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346984#sid=144206134	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 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
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
eMolecules	6843913	https://orderbb.emolecules.com/search/#?query=6843913
mcule	MCULE-3638154542	https://mcule.com/MCULE-3638154542/

PubMed

Title	Date	PubMed
Effect of lintitript, a new CCK-A receptor antagonist, on gastric emptying of a solid-liquid meal in humans.	1998 Jun 30	9712175
Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol.	2014 Apr	24385417

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).

Name

Type

Language

LINTITRIPT

Official Name

English

SR-27897

Code

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