FENPROPOREX DIPHENYLACETATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H12O2.C12H16N2
Molecular Weight	400.5127
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FENPROPOREX DIPHENYLACETATE

Structure Search

SMILES

CC(CC1=CC=CC=C1)NCCC#N.OC(=O)C(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=OPKOXHYTBBMBMX-UHFFFAOYSA-N

InChI=1S/C14H12O2.C12H16N2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12;1-11(14-9-5-8-13)10-12-6-3-2-4-7-12/h1-10,13H,(H,15,16);2-4,6-7,11,14H,5,9-10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C12H16N2
Molecular Weight	188.2688
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C14H12O2
Molecular Weight	212.2439
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27253901
Curator's Comment: description was created based on several sources, including: http://en.pharmacodia.com/web/drug/1_10952.html | http://www.ndrugs.com/?s=fenproporex%20hydrochloride&t=dosage | http://www.doctoralia.com.mx/medicamento/esbelcaps-53723

Fenproporex is a central and indirect-acting sympathomimetic. It was developed as an anorectic drug. Their anorectic effects are believed to be a result of adrenergic activation. Fenproporex has never been approved by the US Food and Drug Administration (FDA) for sale in the US due to lack of efficacy and safety data. There is a paucity of randomized, placebo-controlled trials on Fenproporex. These studies suggest that Fenproporex is modestly effective in promoting weight loss. Data from these studies are insufficient to determine the risk-benefit profile of Fenproporex. Abuse potential and amphetamine-like adverse effects are causes for concern. Adverse effect most frequently reported are: insomnia, anxiety, depression, irritability, dry mouth.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294457	Substrate 661
Cytochrome P450 2B6 19 Target ID: P20813 Gene ID: 1555.0 Gene Symbol: CYP2B6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294457	Substrate 661
Folylpoly-gamma-glutamate synthetase 5 Target ID: CHEMBL2890 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294457	Substrate 661
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294457	Substrate 661
Acetylcholinesterase 207 Target ID: CHEMBL3199 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26247155	Activator 1430
Sodium-Potassium-Exchanging ATPase (Rat) 3 Target ID: Sodium-Potassium-Exchanging ATPase (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24217638	Modulator 828
Adrenergic receptor 35 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19466219 \| https://www.drugbank.ca/drugs/DB01550	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27253901	Primary		Withdrawn	Esbelcaps Approved Use Anorexigenic. Assist in the treatment of obesity. An adjuvant to the establishment of a low-calorie diet.

PubMed

Title	Date	PubMed
A contemporaneous finding of fenproporex in a polydrug suicide.	2001 Oct	11599619
The cerebrospinal fluid/serum leptin ratio during pharmacological therapy for obesity.	2002 Apr	11932292
Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives.	2002 Apr	11897973
Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results.	2002 May	12024689
Amphetamine poisoning in a dog: case report, literature review and veterinary medical perspectives.	2003 Dec	14640484
Treatment of obesity: an update on anti-obesity medications.	2003 Feb	12608525
Fenproporex N-dealkylation to amphetamine--enantioselective in vitro studies in human liver microsomes as well as enantioselective in vivo studies in Wistar and Dark Agouti rats.	2004 Sep 1	15294457
Diabesity: are weight loss medications effective?	2005	15783244
Behavioral neurotoxicity in adolescent and adult mice exposed to fenproporex during pregnancy.	2005 Aug	16138731
Developmental exposure to fenproporex: reproductive and morphological evaluation.	2005 Aug	16138730
Abusive prescription of psychostimulants: a study of two cases.	2006 Mar	16566781
[Prescription, dispensing, and regulation of psychoactive anorexigenic drugs in Belo Horizonte, Minas Gerais, Brazil].	2008 Aug	18709217
Imported fenproporex-based diet pills from Brazil: a report of two cases.	2009 Mar	19096898
Metabolic syndrome, dyslipidemia, hypertension and type 2 diabetes in youth: from diagnosis to treatment.	2010 Aug 18	20718958
Long-term pharmacotherapy for obesity in elderly patients: a retrospective evaluation of medical records from a specialized obesity outpatient clinic.	2010 Jun 1	20524709
An evaluation of the genotoxic and cytotoxic effects of the anti-obesity drugs sibutramine and fenproporex.	2010 Mar	20051455
Dependence on the Brazilian diet pill: a case report.	2010 May-Jun	20525038

Patents

Sample Use Guides

In Vivo Use Guide

The initial dose is 10 mg/day. The dose might be increased up to 15 mg/day.

Route of Administration: Oral

In Vitro Use Guide

In presence of 3 uM inhibitor quinidine and 50 uM Fenproporex the metabolite formation of the S(+)-enantiomer was significantly (P value 0.0145) inhibited.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:55:56 UTC 2023` Edited by `admin` on `Fri Dec 15 18:55:56 UTC 2023`
Record UNII	ROZ625PP27
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENPROPOREX DIPHENYLACETATE

Common Name

English

BENZENEACETIC ACID, .ALPHA.-PHENYL-, COMPD. WITH 3-((1-METHYL-2-PHENYLETHYL)AMINO)PROPANENITRILE (1:1)

Common Name

English

Fenproporex diphenylacetate [WHO-DD]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-PHENYL-, COMPD. WITH (±)-3-((1-METHYL-2-PHENYLETHYL)AMINO)PROPANENITRILE (1:1)

Common Name

English

Code System Code Type Description

CAS

77816-15-0