This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Alaproclate
- DrugBank Accession Number
- DB13233
- Background
Alaproclate was developed as one of the first selective serotonin reuptake inhibitor (SSRI) antidepressants by Astra AB (now AstraZeneca) in the 1970s. Development was discontinued due to concerns over hepatotoxicity observed in animal studies. Alaproclate has also been found to act as a non-competitive NMDA receptor antagonist although without discriminative stimulus properties similar to phencyclidine.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Alaproclate (DB13233)
- Weight
- Average: 255.74
Monoisotopic: 255.1026065 - Chemical Formula
- C13H18ClNO2
- Synonyms
- Alaproclate
- External IDs
- GEA 654
- GEA-654
Pharmacology
- Indication
Not Available
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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
- 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.
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 Alaproclate. Abciximab The risk or severity of hemorrhage can be increased when Alaproclate is combined with Abciximab. Acarbose The risk or severity of hypoglycemia can be increased when Alaproclate is combined with Acarbose. Acebutolol The serum concentration of Acebutolol can be increased when it is combined with Alaproclate. Aceclofenac The risk or severity of gastrointestinal bleeding can be increased when Alaproclate is combined with Aceclofenac. - 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.- Product Ingredients
Ingredient UNII CAS InChI Key Alaproclate hydrochloride NIH506S9US 60719-83-7 OPAKSOWFKIUFNP-UHFFFAOYSA-N
Categories
- ATC Codes
- N06AB07 — Alaproclate
- Drug Categories
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Hypoglycemia-Associated Agents
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Psychoanaleptics
- 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 alpha amino acid esters. These are ester derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid esters
- Alternative Parents
- Alanine and derivatives / Phenylpropanes / Chlorobenzenes / Aryl chlorides / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organochlorides / Organic oxides / Monoalkylamines show 2 more
- Substituents
- Alanine or derivatives / Alpha-amino acid ester / Amine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzenoid / Carbonyl group / Carboxylic acid ester / Chlorobenzene show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- C4R42570ZO
- CAS number
- 60719-82-6
- InChI Key
- FZSPJBYOKQPKCD-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H18ClNO2/c1-9(15)12(16)17-13(2,3)8-10-4-6-11(14)7-5-10/h4-7,9H,8,15H2,1-3H3
- IUPAC Name
- 1-(4-chlorophenyl)-2-methylpropan-2-yl 2-aminopropanoate
- SMILES
- CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C=C1
References
- General References
- Wilkinson A, Courtney M, Westlind-Danielsson A, Hallnemo G, Akerman KE: Alaproclate acts as a potent, reversible and noncompetitive antagonist of the NMDA receptor coupled ion flow. J Pharmacol Exp Ther. 1994 Dec;271(3):1314-9. [Article]
- Nicholson KL, Balster RL: Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats. Psychopharmacology (Berl). 2003 Nov;170(2):215-24. Epub 2003 Jul 8. [Article]
- External Links
- KEGG Drug
- D02787
- PubChem Compound
- 2081
- PubChem Substance
- 347829288
- ChemSpider
- 1997
- BindingDB
- 76298
- ChEBI
- 91544
- ChEMBL
- CHEMBL36591
- Wikipedia
- Alaproclate
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0377 mg/mL ALOGPS logP 2.82 ALOGPS logP 2.88 Chemaxon logS -3.8 ALOGPS pKa (Strongest Basic) 7.34 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.32 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 68.5 m3·mol-1 Chemaxon Polarizability 26.99 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9500000000-9ab546b7f84e068ed9a1 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014r-9800000000-ac30e56f9397ba899b08 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004l-5900000000-89e90521425f31939273 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-7613c30b785a85eb5035 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9300000000-775dae46f11f366a9e0b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-539ae771a897d53e8ba4 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]- 157.43411 predictedDeepCCS 1.0 (2019) [M+H]+ 159.79211 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.88525 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:38 / Updated at February 21, 2021 18:54