Identification

Name
Phendimetrazine
Accession Number
DB01579
Type
Small Molecule
Groups
Approved, 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
  • (2S,3S)-3,4-dimethyl-2-phenylmorpholine
Product Ingredients
IngredientUNIICASInChI Key
Phendimetrazine tartrate6985IP0T80 50-58-8VEPOHXYIFQMVHW-PVJVQHJQSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phendimetrazine TartrateCapsule, extended release105 mg/1OralEon Labs, Inc.1977-09-06Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralA S Medication Solutions1977-09-06Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralPhysicians Total Care, Inc.2009-05-11Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralNucare Pharmaceuticals, Inc.1977-09-06Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralAidarex Pharmaceuticals LLC1977-09-06Not applicableUs00185 5254 01 nlmimage10 ad1fd6de
Phendimetrazine TartrateCapsule, extended release105 mg/1Oralbryant ranch prepack1977-09-06Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralPd Rx Pharmaceuticals, Inc.1977-09-06Not applicableUs
Phendimetrazine TartrateCapsule, extended release105 mg/1OralA S Medication Solutions1977-09-062017-06-20Us
Phendimetrazine TartrateCapsule, extended release105 mg/1OralApotheca, Inc.1977-09-06Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BontrilCapsule105 mg/1OralApotheca, Inc.2010-04-082016-10-13Us
PhendimetrazineTablet35 mg/1OralNorthwind Pharmaceuticals2015-04-22Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralEon Labs, Inc.1997-08-19Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralLife Line Home Care Services2010-09-15Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralProficient Rx LP1997-08-19Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralSolco healthcare U.S., LLC2011-08-01Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralNucare Pharmaceuticals, Inc.1997-08-19Not applicableUs
Phendimetrazine TartrateTablet35 mg/1OralA S Medication Solutions2010-09-152017-06-20Us
Phendimetrazine TartrateTablet35 mg/1OralA S Medication Solutions2010-09-152017-06-20Us
Phendimetrazine TartrateTablet35 mg/1OralAidarex Pharmaceuticals LLC2010-09-15Not applicableUs
International/Other Brands
Adipost / Melfiat / Statobex
Categories
UNII
AB2794W8KV
CAS number
634-03-7
Weight
Average: 191.274
Monoisotopic: 191.131014171
Chemical Formula
C12H17NO
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[[email protected]]1[[email protected]@H](OCCN1C)C1=CC=CC=C1

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.

Structured Indications
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
Human
ASodium-dependent noradrenaline transporter
negative modulator
Human
UAlpha-1B adrenergic receptor
agonist
Human
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

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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Phendimetrazine.Approved
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
KEGG Drug
D08347
KEGG Compound
C07904
ChemSpider
28295
ChEBI
8059
ChEMBL
CHEMBL1744
Therapeutic Targets Database
DAP000574
PharmGKB
PA450902
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phendimetrazine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingBasic ScienceCocaine Use Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
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

Taxonomy

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 / Hydrocarbon derivatives
Substituents
Phenylmorpholine / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Dialkyl ether / Ether / Oxacycle / Azacycle
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
morpholines (CHEBI:8059 )

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284 ]
  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:17016423 ]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126 ]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601 ]
  5. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961 ]
Kind
Protein
Organism
Human
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. [PubMed:17017961 ]
Kind
Protein
Organism
Human
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. [PubMed:17139284 ]
  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:17016423 ]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126 ]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961 ]

Drug created on August 29, 2007 08:52 / Updated on October 02, 2017 05:00