Alaproclate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Alaproclate
Accession Number
DB13233
Type
Small Molecule
Groups
Experimental
Description

Alaproclate is a drug that was being developed as an antidepressant by the Swedish pharmaceutical company Astra AB (now AstraZeneca) in the 1970s. It acts as a selective serotonin reuptake inhibitor (SSRI), and along with zimelidine and indalpine, was one of the first of its kind. Development was discontinued due to the observation of liver complications in rodent studies. In addition to its SSRI properties, alaproclate has been found to act as a non-competitive NMDA receptor antagonist, but does not have discriminative stimulus properties similar to phencyclidine.

Structure
Thumb
Synonyms
Not Available
External IDs
GEA 654 / GEA-654
Product Ingredients
IngredientUNIICASInChI Key
Alaproclate hydrochlorideNIH506S9US60719-83-7OPAKSOWFKIUFNP-UHFFFAOYSA-N
Categories
UNII
C4R42570ZO
CAS number
60719-82-6
Weight
Average: 255.74
Monoisotopic: 255.1026065
Chemical Formula
C13H18ClNO2
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

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 Alaproclate is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of hemorrhage can be increased when Alaproclate is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Alaproclate 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 Alaproclate.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Alaproclate.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Alaproclate.
3,5-diiodothyropropionic acidThe therapeutic efficacy of 3,5-diiodothyropropionic acid can be decreased when used in combination with Alaproclate.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Alaproclate.
4-hydroxycoumarinThe risk or severity of hemorrhage can be increased when Alaproclate is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Alaproclate.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:7996440]
  2. 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. [PubMed:12851738]
External Links
KEGG Drug
D02787
PubChem Compound
2081
PubChem Substance
347829288
ChemSpider
1997
BindingDB
76298
ChEBI
91544
ChEMBL
CHEMBL36591
Wikipedia
Alaproclate
ATC Codes
N06AB07 — Alaproclate

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0377 mg/mLALOGPS
logP2.82ALOGPS
logP2.88ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)7.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.5 m3·mol-1ChemAxon
Polarizability26.99 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 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
Alpha-amino acid ester / Alanine or derivatives / Phenylpropane / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Carboxylic acid ester
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:38 / Updated on November 02, 2018 09:12