AMFONELIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H16N2O3
Molecular Weight	308.3312
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(CC3=CC=CC=C3)C=C2

InChI

InChIKey=WHHHJDGNBVQNAU-UHFFFAOYSA-N

InChI=1S/C18H16N2O3/c1-2-20-11-15(18(22)23)16(21)14-9-8-13(19-17(14)20)10-12-6-4-3-5-7-12/h3-9,11H,2,10H2,1H3,(H,22,23)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24701

Amfonelic acid (AFA) is a dopamine reuptake inhibitor. Experiments on rats have shown that AFA treatment completely prevented the effects of methamphetamine on the dopaminergic system, both morphologically and biochemically.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent dopamine transporter 43 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24701	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Neuropharmacological mechanisms underlying the neuroprotective effects of methylphenidate.	2008-12	19587858
The effects of dopaminergic/serotonergic reuptake inhibition on maternal behavior, maternal aggression, and oxytocin in the rat.	2005-08	15996723
Gestational treatment with cocaine and fluoxetine alters oxytocin receptor number and binding affinity in lactating rat dams.	2004-02-16	15380831
Presynaptic control of striatal dopamine neurotransmission in adult vesicular monoamine transporter 2 (VMAT2) mutant mice.	2003-05	12716422
Effects of norepinephrine and serotonin transporter inhibitors on hyperactivity induced by neonatal 6-hydroxydopamine lesioning in rats.	2002-06	12023542
Regulation of dopamine quantal size in midbrain and hippocampal neurons.	2002-03-10	11864736
A comparison of the patterns of striatal Fos-like immunoreactivity induced by various dopamine agonists in rats.	2000-08-04	10904129

Patents

Sample Use Guides

In Vivo Use Guide

adult rats: Amfonelic acid (AFA) was administered (20 mg/kg, i.p.) at the same time the last methamphetamine (MA) dose was given. AFA treatment completely prevented the effects of MA on the dopaminergic system, both morphologically and biochemically

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Name

Type

Language

NSC-100638

Preferred Name

English

AMFONELIC ACID

Official Name

English

WIN-25978

Code

English

1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-1,4-DIHYDRO-4-OXO-7-(PHENYLMETHYL)-

Common Name

English

AMFONELIC ACID [USAN]

Common Name

English

WIN 25,978

Code

English

7-Benzyl-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Systematic Name

English

amfonelic acid [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47795