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Identification
NameLintitript
Accession NumberDB04867
TypeSmall Molecule
GroupsInvestigational
DescriptionLintitript is a new, highly specific and potent CCK-A receptor antagonist.
Structure
Thumb
SynonymsNot Available
External Identifiers
  • SR 27897
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3YFV00531K
CAS number136381-85-6
WeightAverage: 411.861
Monoisotopic: 411.044439726
Chemical FormulaC20H14ClN3O3S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Indolecarboxylic acid derivative
  • Indolecarboxamide derivative
  • Phenylthiazole
  • N-arylamide
  • Alpha-amino acid or derivatives
  • Indole
  • Pyrrole-2-carboxylic acid or derivatives
  • Pyrrole-2-carboxamide
  • Halobenzene
  • Chlorobenzene
  • 2,4-disubstituted 1,3-thiazole
  • Benzenoid
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiazole
  • Pyrrole
  • Azole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of pancreatic cancer and appetite disorders.
PharmacodynamicsLintitript 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 actionCholecystokinin (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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00854 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:9712175 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 gastrin. It modulates feeding and dopamine-induced behavior in the central and peripheral nervous system. This receptor mediates its action by association with G proteins that activate a phosphatidylinos...
Gene Name:
CCKAR
Uniprot ID:
P32238
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. [PubMed:9712175 ]
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Drug created on October 20, 2007 03:20 / Updated on August 17, 2016 12:24