Phendimetrazine

Identification

Summary

Phendimetrazine is a sympathomimetic amine used as adjunct therapy for the short term management of exogenous obesity.

Brand Names
Fendique
Generic Name
Phendimetrazine
DrugBank Accession Number
DB01579
Background

Phendimetrazine is a weight loss medication. Phendimetrazine is chemically related to amphetamines and is a Schedule III drug under the Convention on Psychotropic Substances and in the US since 1970.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 191.274
Monoisotopic: 191.131014171
Chemical Formula
C12H17NO
Synonyms
  • (2S,3S)-3,4-dimethyl-2-phenylmorpholine
  • Phendimetrazine

Pharmacology

Indication

Used in the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Phendimetrazine is a phenylalkylamine sympathomimetic amine with pharmacological activity similar to the prototype drugs of this class used in obesity, the amphetamines. Actions include central nervous system stimulation and elevation of blood pressure. Tachyphylaxis and tolerance has been demonstrated with all drugs of this class in which these phenomena have been looked for. Drugs of this class used in obesity are commonly known as ''anorectics or anorexigenics." It has not been established, however, that the action of such drugs in treating obesity is primarily one of appetite suppression. Other central nervous system actions or metabolic effects, may be involved.

Mechanism of action

Phendimetrazine may act in a similar way to amphetamines in that it activates the alpha-adrenergic system to induce an appetite suppressive and metabolic increase effect. The drug also acts as a norepinephrine-dopamine releasing agent (NDRA). It can bind to and reverse the NET.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
ASodium-dependent noradrenaline transporter
negative modulator
Humans
UAlpha-1B adrenergic receptor
agonist
Humans
Absorption

Peak plasma levels occur within 1 to 3 hours. Absorption is usually complete by 4 to 6 hours.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Approximately 30% of a given dose of phendimetrazine is metabolized into phenmetrazine, which may account for part of its anorectic effect, and probably also influences abuse potential; individuals who metabolise a greater proportion of phendimetrazine into phenmetrazine are more likely to develop problems with dependence and addiction

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Route of elimination

The major route of elimination is via the kidneys where most of the drug and metabolites are excreted.

Half-life

19-24 hours

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Acute overdosage of phendimetrazine may manifest itself by the following signs and symptoms: unusual restlessness, confusion, belligerance, hallucinations, and panic states. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension, or hypotension and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Poisoning may result in convulsions, coma and death.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Phendimetrazine.
AceclofenacThe risk or severity of hypertension can be increased when Phendimetrazine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Phendimetrazine is combined with Acemetacin.
AcetazolamideAcetazolamide may decrease the excretion rate of Phendimetrazine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Phendimetrazine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Phendimetrazine.
AclidiniumThe risk or severity of Tachycardia can be increased when Phendimetrazine is combined with Aclidinium.
AcrivastinePhendimetrazine may decrease the sedative and stimulatory activities of Acrivastine.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Phendimetrazine.
AlclofenacThe risk or severity of hypertension can be increased when Phendimetrazine is combined with Alclofenac.
Interactions
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Food Interactions
  • Take separate from meals. Take phendimetrazine one hour before eating.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phendimetrazine tartrate6985IP0T8050-58-8VEPOHXYIFQMVHW-PVJVQHJQSA-N
Product Images
International/Other Brands
Adipost / Melfiat / Statobex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fendique ERCapsule, extended release105 mg/1OralVirtus Pharmaceuticals, LLC2020-03-18Not applicableUS flag
Phendimetrazine TartrateCapsule, extended release105 mg/1OralApotheca, Inc.1977-09-06Not applicableUS flag
Phendimetrazine TartrateCapsule, extended release105 mg/1OralNucare Pharmaceuticals, Inc.1977-09-06Not applicableUS flag
Phendimetrazine TartrateCapsule, extended release105 mg/1OralPhysicians Total Care, Inc.2009-05-11Not applicableUS flag54868 307120180907 15195 jr5pf4
Phendimetrazine TartrateCapsule, extended release105 mg/1OralA-S Medication Solutions2018-07-01Not applicableUS flag
Phendimetrazine TartrateCapsule, extended release105 mg/1OralPD-Rx Pharmaceuticals, Inc.1977-09-062019-03-15US flag
Phendimetrazine TartrateCapsule, extended release105 mg/1Oralbryant ranch prepack1977-09-06Not applicableUS flag63629 305120180913 8702 1a62mys
Phendimetrazine TartrateCapsule, extended release105 mg/1OralAidarex Pharmaceuticals LLC1977-09-06Not applicableUS flag00185 5254 01 nlmimage10 ad1fd6de
Phendimetrazine TartrateCapsule, extended release105 mg/1OralCALVIN, SCOTT AND COMPANY, INCORPORATED2018-07-01Not applicableUS flag
Phendimetrazine TartrateCapsule, extended release105 mg/1OralEon Labs, Inc.1977-09-062022-11-30US flag0185 525420180907 15195 t1u9se
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BontrilCapsule105 mg/1OralApotheca, Inc.1982-09-212012-08-31US flag
BontrilCapsule105 mg/1OralValeant Pharmaceuticals1982-09-212012-08-31US flag
Bontril PDMTablet35 mg/1OralValeant Pharmaceuticals1976-12-222015-07-31US flag
PhendimetrazineTablet35 mg/1OralNorthwind Pharmaceuticals2015-04-22Not applicableUS flag
Phendimetrazine TartrateTablet35 mg/1OralKVK-TECH, INC2010-09-15Not applicableUS flag
Phendimetrazine TartrateTablet35 mg/1OralC.O. Truxton, Inc.2001-07-262020-01-12US flag
Phendimetrazine TartrateTablet35 mg/1OralA-S Medication Solutions2010-09-15Not applicableUS flag
Phendimetrazine TartrateTablet35 mg/1OralStat Rx USA1977-08-19Not applicableUS flag
Phendimetrazine TartrateTablet35 mg/1OralPreferred Pharmaceuticals, Inc.1997-08-19Not applicableUS flag
Phendimetrazine TartrateTablet35 mg/1OralElite Laboratories, Inc.2018-01-152020-05-07US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Phenylmorpholines
Alternative Parents
Aralkylamines / Benzene and substituted derivatives / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
morpholines (CHEBI:8059)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
AB2794W8KV
CAS number
634-03-7
InChI Key
MFOCDFTXLCYLKU-CMPLNLGQSA-N
InChI
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
IUPAC Name
(2S,3S)-3,4-dimethyl-2-phenylmorpholine
SMILES
C[C@H]1[C@@H](OCCN1C)C1=CC=CC=C1

References

General References
Not Available
KEGG Drug
D08347
KEGG Compound
C07904
PubChem Compound
30487
PubChem Substance
46506122
ChemSpider
28295
RxNav
33272
ChEBI
8059
ChEMBL
CHEMBL1615439
ZINC
ZINC000022010387
Therapeutic Targets Database
DAP000574
PharmGKB
PA450902
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phendimetrazine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceCocaine Use Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Calvin Scott and Co. Inc.
  • D.M. Graham Laboratories Inc.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • H and H Laboratories
  • Kraft Pharmaceutical Co. Inc.
  • Macnary Ltd.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Mikart Inc.
  • Nexgen Pharma Inc.
  • Nucare Pharmaceuticals Inc.
  • Numark Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharma Pac LLC
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Quality Research Pharmaceutical Inc.
  • Rebel Distributors Corp.
  • Schering Corp.
  • Southwood Pharmaceuticals
  • United Research Laboratories Inc.
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
CapsuleOral105 mg/1
Capsule, extended releaseOral105 mg/1
TabletOral35 mg/1
Prices
Unit descriptionCostUnit
Bontril Slow Release 105 mg 24 Hour Capsule1.67USD capsule
Bontril sr 105 mg capsule1.1USD capsule
Phendimetrazine Tartrate 105 mg 24 Hour Capsule1.07USD capsule
Bontril pdm 35 mg tablet0.83USD tablet
Bontril 105 mg capsule sa0.48USD capsule
Phendimetrazine Tartrate 35 mg tablet0.24USD tablet
Phendimetrazine 35 mg tablet0.21USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)134.5 °C at 1.20E+01 mm HgNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.43 mg/mLALOGPS
logP2.01ALOGPS
logP2.17ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)7.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.76 m3·mol-1ChemAxon
Polarizability22.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.9846
Caco-2 permeable+0.7977
P-glycoprotein substrateSubstrate0.6041
P-glycoprotein inhibitor INon-inhibitor0.6769
P-glycoprotein inhibitor IINon-inhibitor0.9583
Renal organic cation transporterInhibitor0.643
CYP450 2C9 substrateNon-substrate0.8398
CYP450 2D6 substrateSubstrate0.6133
CYP450 3A4 substrateSubstrate0.6142
CYP450 1A2 substrateNon-inhibitor0.7819
CYP450 2C9 inhibitorNon-inhibitor0.9346
CYP450 2D6 inhibitorNon-inhibitor0.6649
CYP450 2C19 inhibitorNon-inhibitor0.6534
CYP450 3A4 inhibitorNon-inhibitor0.8458
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8231
Ames testNon AMES toxic0.8256
CarcinogenicityNon-carcinogens0.9313
BiodegradationNot ready biodegradable0.9087
Rat acute toxicity2.6514 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7016
hERG inhibition (predictor II)Non-inhibitor0.7799
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.7 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [Article]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [Article]
  5. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [Article]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  6. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [Article]

Drug created on August 29, 2007 14:52 / Updated on July 08, 2021 05:43