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regarding adverse effects caused by SSRIs, and reported hematological effects caused by Indalpine, it was abruptly withdrawn from the US market.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- Investigational, Withdrawn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
Structure for Indalpine (DB08953)
- Weight
- Average: 228.3327
Monoisotopic: 228.16264865 - Chemical Formula
- C15H20N2
- Synonyms
- Indalpine
- External IDs
- LM-5008
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Indalpine. Abametapir The serum concentration of Indalpine can be increased when it is combined with Abametapir. Abciximab The risk or severity of hemorrhage can be increased when Indalpine is combined with Abciximab. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Indalpine. Abiraterone The metabolism of Indalpine can be decreased when combined with Abiraterone. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Upstène (Pharmuka)
Categories
- Drug Categories
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Hypoglycemia-Associated Agents
- Membrane Transport Modulators
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Psychotropic Drugs
- Selective Serotonin Reuptake Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- 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
- 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]
- Galbaud du Fort G: [Hematologic toxicity of antidepressive agents]. Encephale. 1988 Jul-Aug;14(4):307-18. [Article]
- External Links
- PubChem Compound
- 44668
- PubChem Substance
- 310264918
- ChemSpider
- 40643
- BindingDB
- 50029150
- ChEBI
- 134939
- ChEMBL
- CHEMBL276520
- ZINC
- ZINC000004674528
- Wikipedia
- Indalpine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 167 U.S. Patent 4,064,255. - Predicted Properties
Property Value Source Water Solubility 0.0125 mg/mL ALOGPS logP 3.58 ALOGPS logP 3.07 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 17.32 Chemaxon pKa (Strongest Basic) 10.36 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 27.82 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 71.77 m3·mol-1 Chemaxon Polarizability 27.59 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-9620000000-1fa89594f786498151e6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-bbca09e7e5269b9b3444 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-57b4ca098028cf84757b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-2290000000-909e0ae4de165cd06978 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-4c67c636a3467237b00f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00r7-1920000000-be992740dc1fadfe5d3e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f9w-0910000000-2399fb69120e53c246b7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 163.1708301 predictedDarkChem Lite v0.1.0 [M-H]- 147.71484 predictedDeepCCS 1.0 (2019) [M+H]+ 164.3648301 predictedDarkChem Lite v0.1.0 [M+H]+ 150.11043 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.0512301 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.22408 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- 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 at May 28, 2014 17:04 / Updated at February 21, 2021 18:52