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

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H17NO.C4H6O6
Molecular Weight 341.3563
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENDIMETRAZINE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)C2=CC=CC=C2

InChI

InChIKey=VEPOHXYIFQMVHW-PVJVQHJQSA-N
InChI=1S/C12H17NO.C4H6O6/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11;5-1(3(7)8)2(6)4(9)10/h3-7,10,12H,8-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t10-,12+;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula C12H17NO
Molecular Weight 191.2695
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.0868
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 Wed Jul 05 22:36:38 UTC 2023
Edited
by admin
on Wed Jul 05 22:36:38 UTC 2023
Record UNII
6985IP0T80
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENDIMETRAZINE TARTRATE
MART.   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
DI-METREX
Brand Name English
PHENDIMETRAZINE TARTRATE [VANDF]
Common Name English
PHENAZINE
Systematic Name English
MELFIAT
Brand Name English
BONTRIL
Brand Name English
PLEGINE
Brand Name English
PHENDIMETRAZINE TARTRATE [USP IMPURITY]
Common Name English
SPRX-105
Brand Name English
ALPHAZINE
Brand Name English
STATOBEX
Brand Name English
PHENDIMETRAZINE TARTRATE [MART.]
Common Name English
(2S,3S)-3,4-DIMETHYL-2-PHENYLMORPHOLINE L-(+)-TARTRATE
Systematic Name English
Phendimetrazine tartrate [WHO-DD]
Common Name English
ADPHEN
Brand Name English
X-TROZINE
Brand Name English
APPECON
Brand Name English
SPRX-3
Brand Name English
PHENDIMETRAZINE BITARTRATE
MI  
Common Name English
MORPHOLINE, 3,4-DIMETHYL-2-PHENYL-, TARTRATE, D-
Common Name English
STATOBEX-G
Brand Name English
PHENDIMETRAZINE HYDROGEN TARTRATE
Common Name English
PHENDIMETRAZINE TARTRATE [USP-RS]
Common Name English
PHENDIMETRAZINE TARTRATE [USP MONOGRAPH]
Common Name English
PHENDIMETRAZINE TARTRATE [ORANGE BOOK]
Common Name English
BONTRIL PDM
Brand Name English
ADIPOST
Brand Name English
PHENDIMETRAZINE TARTRATE CIII
USP-RS  
Common Name English
PHENDIMETRAZINE BITARTRATE [MI]
Common Name English
CAM-METRAZINE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
DEA NO. 1615
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
NCI_THESAURUS C29728
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT001250
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
MERCK INDEX
M8604
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C47667
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
RXCUI
58157
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY RxNorm
PUBCHEM
120608
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-051-0
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
EVMPD
SUB03739MIG
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
CHEBI
36674
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
CAS
50-58-8
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
FDA UNII
6985IP0T80
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
DAILYMED
6985IP0T80
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID70198165
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL1744
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1516502
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
SMS_ID
100000088259
Created by admin on Wed Jul 05 22:36:38 UTC 2023 , Edited by admin on Wed Jul 05 22:36:38 UTC 2023
PRIMARY
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