BENZPHETAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H21N
Molecular Weight	239.3553
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](CC1=CC=CC=C1)N(C)CC2=CC=CC=C2

InChI

InChIKey=YXKTVDFXDRQTKV-HNNXBMFYSA-N

InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3fd6b3a8-b17b-4b98-ad03-a8af7b6f3368

Benzphetamine is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone. Presumably, benzphetamine produces its effects through mechanisms similar to amphetamine via induces synaptic vesicular amine transporter, but precise mechanism of action of benzphetamine is not known.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Synaptic vesicular amine transporter 57 Target ID: CHEMBL1893 Sources: https://books.google.ru/books?id=XUtgDAAAQBAJ&pg=PA218&lpg=PA218&dq=bENZPHETAMINE+Synaptic+vesicular+amine+transporter&source=bl&ots=vGwA9UhTd7&sig=ciM1iShwqrLHYOZAqh8D0S0AGWs&hl=ru&sa=X&ved=0ahUKEwjSvKHijKrUAhVQaVAKHfDBD4UQ6AEIWTAH#v=onepage&q=bENZPHETAMINE%20Synaptic%20vesicular%20amine%20transporter&f=false	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Exogenous obesity 19 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3fd6b3a8-b17b-4b98-ad03-a8af7b6f3368	Palliative		Approved 8429	BENZPHETAMINE HYDROCHLORIDE Approved Use Benzphetamine hydrochloride tablets are indicated in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone. Benzphetamine hydrochloride tablets are indicated for use as monotherapy only. Launch Date 2006

AUC

Value	Dose	Co-administered	Analyte	Population
4.9 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8787790	10 mg/kg 1 times / day multiple, intraperitoneal dose: 10 mg/kg route of administration: Intraperitoneal experiment type: MULTIPLE co-administered:		BENZPHETAMINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
13% OTHER https://go.drugbank.com/drugs/DB00865			BENZPHETAMINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	Other AEs: Gastrointestinal signs and symptoms, Dizziness... Other AEs: Gastrointestinal signs and symptoms (5 patients) Dizziness (4 patients) Constipation (2 patients) Nervousness (5 patients) Pruritus (1 patient) Dry mouth (3 patients) Chest pain (1 patient) Headache (1 patient) Malaise (1 patient) Fatigue (1 patient) Appetite disorder (1 patient) Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext

AEs

AE	Significance	Dose	Population
Appetite disorder	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Chest pain	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Fatigue	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Headache	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Malaise	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Pruritus	1 patient	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Constipation	2 patients	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Dry mouth	3 patients	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Dizziness	4 patients	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Gastrointestinal signs and symptoms	5 patients	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext
Nervousness	5 patients	80 mg 3 times / day multiple, oral (max) Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext	unhealthy, 54 n = 20 Health Status: unhealthy Condition: Obesity Age Group: 54 Sex: F Population Size: 20 Sources: https://academic.oup.com/ajcn/article-abstract/9/5/632/4730120?redirectedFrom=fulltext

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737		substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP450 65 CYP3A 191 CYP2B 10 CYP2B1 12

Drug as victim

Target	Modality	Activity
CYP2B 10	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0003986104000256 Page: 278.0	yes
CYP2B1 12	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0003986104000256 Page: 284.0	yes
CYP2D6 1217	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/004982500237686 Page: 297.0	yes
CYP3A 191	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/096007609390152M Page: abstract	yes
CYP3A4 1737	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/004982500237686 Page: 305.0	yes
CYP450 65	substrate 3367 Sources: https://portlandpress.com/biochemsoctrans/article-abstract/9/1/57/87237/Effects-of-spermine-and-albumin-on-hepatic?redirectedFrom=fulltext Page: 1981.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3044	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3044
ChemicalBook	CB3705216	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3705216
ZINC	ZINC000000968305	http://zinc15.docking.org/substances/ZINC000000968305

PubMed

Title	Date	PubMed
Characterization of rabbit liver P450IIE1 synthesized in transformed yeast cells.	1990 Oct	2292581
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation.	2005 Jun	15769884
Resonance Raman studies of cytochrome P450 2B4 in its interactions with substrates and redox partners.	2008 Mar 25	18311926
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection.	2009 Jun	19299527

Patents

Sample Use Guides

In Vivo Use Guide

Dosage should be individualized according to the response of the patient. The suggested dosage ranges from 25 to 50 mg one to three times daily. Treatment should begin with 25 to 50 mg once daily with subsequent increase in individual dose or frequency according to response. A single daily dose is preferably given in mid-morning or mid-afternoon, according to the patient's eating habits. In an occasional patient it may be desirable to avoid late afternoon administration. Use of benzphetamine hydrochloride is not recommended in individuals under 12 years of age.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

BENZPHETAMINE

Common Name

English

(+)-BENZPHETAMINE

Common Name

English

BENZFETAMINE

Official Name

English

BENZPHETAMINE [VANDF]

Common Name

English

BENZPHETAMINE [MI]

Common Name

English

BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-N-(PHENYLMETHYL)-, (.ALPHA.S)-

Common Name

English

Benzfetamine [WHO-DD]

Common Name

English

(+)-N-BENZYL-N,.ALPHA.-DIMETHYLPHENETHYLAMINE

Systematic Name

English

BENZPHETAMINE [HSDB]

Common Name

English

benzfetamine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29728