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Identification
NamePhendimetrazine
Accession NumberDB01579
TypeSmall Molecule
GroupsApproved, Illicit
Description

Phendimetrazine is a weight loss medication. Phendimetrazine is chemically related to amphetamines and is a Schedule III drug under the Convention on Psychotropic Substances. In the United States, phendimetrazine is a Schedule III controlled substance under the Uniform Controlled Substances Act of 1970.

Structure
Thumb
Synonyms
SynonymLanguageCode
PhendimetrazineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bontrilcapsule105 mgoralApotheca, Inc.2010-04-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AdipostNot Available
MelfiatNot Available
StatobexNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number634-03-7
WeightAverage: 191.2695
Monoisotopic: 191.131014171
Chemical FormulaC12H17NO
InChI KeyMFOCDFTXLCYLKU-UHFFFAOYSA-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
IUPAC Name
3,4-dimethyl-2-phenylmorpholine
SMILES
CC1C(OCCN1C)C1=CC=CC=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.
PharmacodynamicsPhendimetrazine 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 actionPhendimetrazine 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.
AbsorptionPeak plasma levels occur within 1 to 3 hours. Absorption is usually complete by 4 to 6 hours.
Volume of distributionNot Available
Protein bindingNot 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

SubstrateEnzymesProduct
Phendimetrazine
Not Available
PhenmetrazineDetails
Route of eliminationThe major route of elimination is via the kidneys where most of the drug and metabolites are excreted.
Half life19-24 hours
ClearanceNot Available
ToxicityAcute 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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9346
CYP450 2D6 substrateNon-inhibitor0.6649
CYP450 2C19 substrateNon-inhibitor0.6534
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral105 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
boiling point134.5 °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
Polarizability21.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.7 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ChlorpromazineDecreased anorexic effect, may increases psychotic symptoms
FluoxetineRisk of serotoninergic syndrome
FluphenazineDecreased anorexic effect, may increase psychotic symptoms
FluvoxamineRisk of serotoninergic syndrome
GuanethidinePhendimetrazine may decrease the effect of guanethidine.
IsocarboxazidPossible hypertensive crisis
MesoridazineDecreased anorexic effect, may increase psychotic symptoms
MethotrimeprazineDecreased anorexic effect, may increase psychotic symptoms
ParoxetineRisk of serotoninergic syndrome
PerphenazineDecreased anorexic effect, may increase psychotic symptoms
PhenelzinePossible hypertensive crisis
ProchlorperazineDecreased anorexic effect, may increase pyschotic symptoms
PromethazineDecreased anorexic effect, may increase pyschotic symptoms
PropericiazineDecreased anorexic effect, may increase pyschotic symptoms
RasagilinePossible hypertensive crisis
ThioridazineDecreased anorexic effect, may increase psychotic symptoms
TramadolIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TrandolaprilPhendimetrazine may reduce the efficacy of Trandolapril.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Phendimetrazine. Concomitant therapy should be avoided.
TrifluoperazineDecreased anorexic effect, may increase psychotic symptoms
TriprolidineTriprolidine may reduce the sedative effect of the antihistamine, Phendimetrazine.
Food InteractionsNot Available

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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. Pubmed
  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. Pubmed
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. Pubmed
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. Pubmed
  5. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed

2. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: negative modulator

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed

3. Alpha-1B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

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. Pubmed
  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. Pubmed
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. Pubmed
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  6. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed

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Drug created on August 29, 2007 08:52 / Updated on January 29, 2014 08:32