NAV

Lintitript

Identification

Generic Name
Lintitript
DrugBank Accession Number
DB04867
Background

Lintitript is a new, highly specific and potent CCK-A receptor antagonist.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 411.861
Monoisotopic: 411.044439726
Chemical Formula
C20H14ClN3O3S
Synonyms
  • Lintitript
External IDs
  • SR 27897
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

For the treatment of pancreatic cancer and appetite disorders.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Lintitript SR 27897 is a selective cholecystokinin type A (CCK-A) receptor antagonist. In February 2000, Sanofi announced that it was halting development of the drug for appetite disorders, and in September 2002, Sanofi announced that it had stopped investigation all together.

Mechanism of action

Cholecystokinin (CCK) modulates feeding and dopamine-induced behavior in the central and peripheral nervous system. Lintitript antagonizes the effect of cholecystokinin by binding to the cholecystokinin type A (CCK-A) receptor. This action presumably alters feeding habits, however the exact mechanism of action is not known.

TargetActionsOrganism
UCholecystokinin receptor type ANot AvailableHumans
Absorption

Not Available

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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indolyl carboxylic acids and derivatives
Alternative Parents
Alpha amino acids and derivatives / N-alkylindoles / Indoles / 2,4-disubstituted thiazoles / Chlorobenzenes / Substituted pyrroles / Aryl chlorides / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
show 9 more
Substituents
2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Carbonyl group / Carboximidic acid
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
3YFV00531K
CAS number
136381-85-6
InChI Key
ILNRQFBVVQUOLP-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(2-{[4-(2-chlorophenyl)-1,3-thiazol-2-yl]carbamoyl}-1H-indol-1-yl)acetic acid
SMILES
OC(=O)CN1C(=CC2=CC=CC=C12)C(=O)NC1=NC(=CS1)C1=CC=CC=C1Cl

References

General References
  1. Kreiss C, Schwizer W, Borovicka J, Jansen JB, Bouloux C, Pignol R, Bischof Delaloye A, Fried M: Effect of lintitript, a new CCK-A receptor antagonist, on gastric emptying of a solid-liquid meal in humans. Regul Pept. 1998 Jun 30;74(2-3):143-9. [Article]
PubChem Compound
122077
PubChem Substance
175426876
ChemSpider
108883
BindingDB
82304
ChEBI
92624
ChEMBL
CHEMBL249973
ZINC
ZINC000000537914
PDBe Ligand
1OE
PDB Entries
7f8u

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00856 mg/mLALOGPS
logP4.27ALOGPS
logP4.77Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.19Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area84.22 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity107.79 m3·mol-1Chemaxon
Polarizability39.75 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8956
Blood Brain Barrier+0.6572
Caco-2 permeable-0.6096
P-glycoprotein substrateNon-substrate0.5717
P-glycoprotein inhibitor INon-inhibitor0.8211
P-glycoprotein inhibitor IINon-inhibitor0.6439
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.7338
CYP450 2D6 substrateNon-substrate0.8452
CYP450 3A4 substrateNon-substrate0.6075
CYP450 1A2 substrateInhibitor0.579
CYP450 2C9 inhibitorInhibitor0.7831
CYP450 2D6 inhibitorNon-inhibitor0.8294
CYP450 2C19 inhibitorInhibitor0.6289
CYP450 3A4 inhibitorNon-inhibitor0.6504
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8393
Ames testNon AMES toxic0.7209
CarcinogenicityNon-carcinogens0.7401
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.3523 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.986
hERG inhibition (predictor II)Inhibitor0.5068
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0002900000-03364b969cfcc70f63f1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0001900000-e8ba2058ab76ad4ae39e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2001900000-743b27f182fd9ca36b90
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02u0-0339600000-ace002dc7efb0b629aa5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0901000000-551084b12a6165054787
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0900000000-f157fe78b05130821d1d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.37508
predicted
DeepCCS 1.0 (2019)
[M+H]+183.73308
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.7339
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Cholecystokinin receptor type A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptide binding
Specific Function
Receptor for cholecystokinin. Mediates pancreatic growth and enzyme secretion, smooth muscle contraction of the gall bladder and stomach. Has a 1000-fold higher affinity for CCK rather than for gas...
Gene Name
CCKAR
Uniprot ID
P32238
Uniprot Name
Cholecystokinin receptor type A
Molecular Weight
47840.645 Da
References
  1. Kreiss C, Schwizer W, Borovicka J, Jansen JB, Bouloux C, Pignol R, Bischof Delaloye A, Fried M: Effect of lintitript, a new CCK-A receptor antagonist, on gastric emptying of a solid-liquid meal in humans. Regul Pept. 1998 Jun 30;74(2-3):143-9. [Article]

Drug created at October 20, 2007 09:20 / Updated at February 21, 2021 18:51