U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H17NO
Molecular Weight 191.2699
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENDIMETRAZINE

SMILES

C[C@@]1([H])[C@]([H])(c2ccccc2)OCCN1C

InChI

InChIKey=MFOCDFTXLCYLKU-CMPLNLGQSA-N
InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3/t10-,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula C12H17NO
Molecular Weight 191.2699
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/pro/phendimetrazine.html | http://www.wikidoc.org/index.php/Phendimetrazine

Phendimetrazine is an appetite suppressant that is FDA approved for the treatment of exogenous obesity. It is clinically available anorectic agent, which display minimal interactions with monoamine transporters in vitro. On the other hand, their medications is known to be psychomotor stimulants when administered in vivo as indicated by their shared properties with illicit drugs like cocaine. The following adverse reactions are described, or described in greater detail, in other sections: Primary pulmonary hypertension; Valvular heart disease; Effect on the ability to engage in potentially hazardous tasks; Withdrawal effects following prolonged high dosage administration. Use of phendimetrazine tartrate is contraindicated during or within 14 days following the administration of monoamine oxidase inhibitors because of the risk of hypertensive crisis.

Originator

Sources: DOI:10.1002/ange.19560680508

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.56 µM [EC50]
8.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHENDIMETRAZINE TARTRATE

Approved Use

Phendimetrazine tartrate is indicated in the management of exogenous obesity as a short term adjunct (a few weeks) 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. Below is a chart of Body Mass Index (BMI) based on various heights and weights. BMI is calculated by taking the patient’s weight, in kilograms (kg), divided by the patient’s height, in meters (m), squared. Metric conversions are as follows: pounds ÷ 2.2 = kg; inches x 0.0254 = meters. BODY MASS INDEX (BMI), kg/m2 Height (feet, inches) Weight(pounds) 5’0” 5’3” 5’6” 5’9” 6’0” 6’3” 140 27 25 23 21 19 18 150 29 27 24 22 20 19 160 31 28 26 24 22 20 170 33 30 28 25 23 21 180 35 32 29 27 25 23 190 37 34 31 28 26 24 200 39 36 32 30 27 25 210 41 37 34 31 29 26 220 43 39 36 33 30 28 230 45 41 37 34 31 29 240 47 43 39 36 33 30 250 49 44 40 37 34 31 Phendimetrazine tartrate is indicated for use as monotherapy only.

Launch Date

2.930688E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1227 ng/mL
3.2 mg/kg single, intramuscular
dose: 3.2 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
137 ng/mL
0.32 mg/kg single, intramuscular
dose: 0.32 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
268 ng/mL
1 mg/kg single, intramuscular
dose: 1 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
70 ng/mL
35 mg single, oral
dose: 35 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
132945 ng × min/mL
3.2 mg/kg single, intramuscular
dose: 3.2 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
15.195 ng × min/mL
0.32 mg/kg single, intramuscular
dose: 0.32 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
35.877 ng × min/mL
1 mg/kg single, intramuscular
dose: 1 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
112 min
3.2 mg/kg single, intramuscular
dose: 3.2 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
114 min
0.32 mg/kg single, intramuscular
dose: 0.32 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
180 min
1 mg/kg single, intramuscular
dose: 1 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Macaca mulatta
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2 h
35 mg single, oral
dose: 35 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENDIMETRAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.7 h
PHENDIMETRAZINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
anorectic agents
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Disc. AE: Pulmonary hypertension...
AEs leading to
discontinuation/dose reduction:
Pulmonary hypertension
Sources:
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
dexfenfluramine
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Disc. AE: Valvular heart disease NOS...
AEs leading to
discontinuation/dose reduction:
Valvular heart disease NOS
Sources:
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
fenfluramine
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Disc. AE: Valvular heart disease NOS...
AEs leading to
discontinuation/dose reduction:
Valvular heart disease NOS
Sources:
AEs

AEs

AESignificanceDosePopulation
Pulmonary hypertension Disc. AE
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
anorectic agents
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Valvular heart disease NOS Disc. AE
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
dexfenfluramine
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Valvular heart disease NOS Disc. AE
105 mg 1 times / day steady, oral
Recommended
Dose: 105 mg, 1 times / day
Route: oral
Route: steady
Dose: 105 mg, 1 times / day
Co-administed with::
fenfluramine
Sources:
unhealthy
Health Status: unhealthy
Condition: exogenous obesity
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Safety and tolerability of intranasal cocaine during phendimetrazine maintenance.
2016 Jun
Attenuation of cocaine self-administration by chronic oral phendimetrazine in rhesus monkeys.
2016 Jun 2
Abuse Potential of Oral Phendimetrazine in Cocaine-dependent Individuals: Implications for Agonist-like Replacement Therapy.
2016 May-Jun
Patents

Sample Use Guides

One extended-release capsule (105 mg phendimetrazine tartrate) in the morning (30 to 60 minutes before morning meal).
Route of Administration: Oral
Racemic phendimetrazine was essentially inactive at [3H]dopamine, [3H]norepinephrine, and [3H]5-HT uptake inhibition and release. The most potent effect of phendimetrazine was inhibition of [3H]norepinephrine uptake, with an IC50 of 8300 nM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:17:32 UTC 2021
Edited
by admin
on Sat Jun 26 08:17:32 UTC 2021
Record UNII
AB2794W8KV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENDIMETRAZINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENDIMETRAZINE [HSDB]
Common Name English
NSC-169187
Code English
PHENDIMETRAZINE [MI]
Common Name English
PHENDIMETRAZINE [VANDF]
Common Name English
(+)-PHENDIMETRAZINE
Common Name English
(2S,3S)-3,4-DIMETHYL-2-PHENYLMORPHOLINE
Systematic Name English
MORPHOLINE, 3,4-DIMETHYL-2-PHENYL-, (2S-TRANS)-
Systematic Name English
PHENDIMETRAZINE [WHO-DD]
Common Name English
PHENDIMETRAZINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
NDF-RT N0000175372
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
NDF-RT N0000175372
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
NDF-RT N0000175651
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
NDF-RT N0000175423
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
DEA NO. 1615
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
LIVERTOX 767
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
Code System Code Type Description
PUBCHEM
30487
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
INN
982
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
CAS
634-03-7
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
NCI_THESAURUS
C61887
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
DRUG BANK
DB01579
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
RXCUI
33272
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY RxNorm
FDA UNII
AB2794W8KV
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
MESH
C100294
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
MERCK INDEX
M8604
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2122
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
EVMPD
SUB09756MIG
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
HSDB
3381
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
EPA CompTox
634-03-7
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
WIKIPEDIA
PHENDIMETRAZINE
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL1744
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-204-6
Created by admin on Sat Jun 26 08:17:32 UTC 2021 , Edited by admin on Sat Jun 26 08:17:32 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC