Indalpine

Identification

Generic Name
Indalpine
DrugBank Accession Number
DB08953
Background

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regarding adverse effects caused by SSRIs, and reported hematological effects caused by Indalpine, it was abruptly withdrawn from the US market.

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
Thumb
Weight
Average: 228.3327
Monoisotopic: 228.16264865
Chemical Formula
C15H20N2
Synonyms
  • Indalpine
External IDs
  • LM-5008

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Indalpine.
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Indalpine.
AbametapirThe serum concentration of Indalpine can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of hemorrhage can be increased when Indalpine is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Indalpine.
AbirateroneThe metabolism of Indalpine can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Indalpine.
AcarboseThe risk or severity of hypoglycemia can be increased when Indalpine is combined with Acarbose.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Indalpine.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Indalpine is combined with Aceclofenac.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Upstène (Pharmuka)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
V35562QSVT
CAS number
63758-79-2
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

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. [Article]
  2. Galbaud du Fort G: [Hematologic toxicity of antidepressive agents]. Encephale. 1988 Jul-Aug;14(4):307-18. [Article]
PubChem Compound
44668
PubChem Substance
310264918
ChemSpider
40643
BindingDB
50029150
ChEBI
134939
ChEMBL
CHEMBL276520
ZINC
ZINC000004674528
Wikipedia
Indalpine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Enzymes

Kind
Protein
Organism
Humans
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. [Article]

Drug created on May 28, 2014 17:04 / Updated on February 21, 2021 18:52