ALAPROCLATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H18ClNO2
Molecular Weight	255.741
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C=C1

InChI

InChIKey=FZSPJBYOKQPKCD-UHFFFAOYSA-N

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6205120 | https://www.ncbi.nlm.nih.gov/pubmed/7936117 | https://www.ncbi.nlm.nih.gov/pubmed/3883697 | https://www.ncbi.nlm.nih.gov/pubmed/6433393/

Alaproclate is a selective 5-HT uptake inhibitor. Alaproclate enantiomers block potassium and NMDA receptor currents in a stereoselective manner. Alaproclate was practically devoid of action on a number of receptors as examined in binding studies in vitro: 5-HT, histamine-H1, alpha 1, -alpha 2-adrenergic and dopamine D2 receptors. Alaproclate was investigated in trials for the treatment of depression and dementia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 46 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996440 \| https://www.ncbi.nlm.nih.gov/pubmed/12851738	Antagonist 2778		0.3 µM [IC50]
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996440	Inhibitor 8297

PubMed

Title	Date	PubMed
Endogenous activation of serotonin-2A receptors is required for respiratory rhythm generation in vitro.	2002 Dec 15	12486201
Cocaine-induced brain activation determined by positron emission tomography neuroimaging in conscious rhesus monkeys.	2002 Jan	11862343
Serotonergic attenuation of the reinforcing and neurochemical effects of cocaine in squirrel monkeys.	2002 Mar	11861788
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.	2003 Feb	12459931
Open space swimming test to index antidepressant activity.	2003 Jun 15	12788500
Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats.	2003 Nov	12851738
Inhibitory actions of serotonin on glutamate release in dorsal medulla suppress systemic arterial pressure of cats.	2004 Jan 23	14729238
Tamoxifen's protection against breast cancer recurrence is not reduced by concurrent use of the SSRI citalopram.	2008 Aug 19	18665165
Alpha-2 adrenergic-induced changes in rectal temperature in adult and 13-day old rats following acute and repeated desipramine administration.	2008 Oct 2	18831759
Chronic fluoxetine treatment increases daytime melatonin synthesis in the rodent.	2009	22291481
Effects of serotonergic agents on survival and hemolymph composition of the larval mosquito Aedes aegypti (Diptera: Culicidae, L.) in vivo: does serotonin regulate hemolymph acid-base homeostasis?	2009 Nov	19880735

Patents

Name

Type

Language

ALAPROCLATE

Official Name

English

Alaproclate [WHO-DD]

Common Name

English

ALAPROCLATE [USAN]

Common Name

English

GEA-654

Code

English

alaproclate [INN]

Common Name

English

DL-ALANINE, 2-(4-CHLOROPHENYL)-1,1-DIMETHYLETHYL ESTER

Systematic Name

English

NSC-758657

Code

English

ALAPROCLATE [MART.]

Common Name

English

DL-ALANINE P-CHLORO-.ALPHA.,.ALPHA.-DIMETHYLPHENETHYL ESTER.

Systematic Name

English

GEA 654

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C265