Identification

Name
Indalpine
Accession Number
DB08953
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

Indalpine was one of the first selective serotonin reuptake inhibitors to reach the American market. It was initially marketed by Pharmuka. However, after the emergence of widespread concern regarding adverse effects caused by SSRIs, and reported hematological effects caused by Indalpine, it was abruptly withdrawn from the US market.

Structure
Thumb
Synonyms
Not Available
External IDs
LM-5008
International/Other Brands
Upstène (Pharmuka)
Categories
UNII
V35562QSVT
CAS number
63758-79-2
Weight
Average: 228.3327
Monoisotopic: 228.16264865
Chemical Formula
C15H20N2
InChI Key
SADQVAVFGNTEOD-UHFFFAOYSA-N
InChI
InChI=1S/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2
IUPAC Name
3-[2-(piperidin-4-yl)ethyl]-1H-indole
SMILES
C(CC1=CNC2=CC=CC=C12)C1CCNCC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of hemorrhage can be increased when Indalpine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of hemorrhage can be increased when Indalpine is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Indalpine is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Indalpine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Indalpine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Indalpine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Indalpine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Indalpine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Indalpine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Indalpine.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 4,064,255.

General References
  1. Marcin LR, Mattson RJ, Gao Q, Wu D, Molski TF, Mattson GK, Lodge NJ: Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles. Bioorg Med Chem Lett. 2010 Feb 1;20(3):1027-30. doi: 10.1016/j.bmcl.2009.12.043. Epub 2009 Dec 16. [PubMed:20034793]
  2. Galbaud du Fort G: [Hematologic toxicity of antidepressive agents]. Encephale. 1988 Jul-Aug;14(4):307-18. [PubMed:3058454]
External Links
PubChem Compound
44668
PubChem Substance
310264918
ChemSpider
40643
BindingDB
50029150
ChEBI
134939
ChEMBL
CHEMBL276520
Wikipedia
Indalpine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)167 U.S. Patent 4,064,255.
Predicted Properties
PropertyValueSource
Water Solubility0.0125 mg/mLALOGPS
logP3.58ALOGPS
logP3.07ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.32ChemAxon
pKa (Strongest Basic)10.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area27.82 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.77 m3·mol-1ChemAxon
Polarizability27.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Aralkylamines / Substituted pyrroles / Piperidines / Benzenoids / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
3-alkylindole / Aralkylamine / Piperidine / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Secondary aliphatic amine / Secondary amine / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gerotziafas GT, Mahe I, Elalamy I: New orally active anticoagulant agents for the prevention and treatment of venous thromboembolism in cancer patients. Ther Clin Risk Manag. 2014 Jun 13;10:423-36. doi: 10.2147/TCRM.S49063. eCollection 2014. [PubMed:24966680]

Drug created on May 28, 2014 11:04 / Updated on November 02, 2018 06:56