Phendimetrazine
Identification
- Name
- Phendimetrazine
- Accession Number
- DB01579
- 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 and in the US since 1970.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Phendimetrazine (DB01579)
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans ASodium-dependent noradrenaline transporter negative modulatorHumans UAlpha-1B adrenergic receptor agonistHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- 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
- 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.
Drug Interaction Unlock Additional DataAcebutolol The therapeutic efficacy of Phendimetrazine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Phendimetrazine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Phendimetrazine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Phendimetrazine. Aclidinium The risk or severity of Tachycardia can be increased when Phendimetrazine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Phendimetrazine. Alclofenac The risk or severity of hypertension can be increased when Phendimetrazine is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Phendimetrazine. Alfuzosin The therapeutic efficacy of Phendimetrazine can be decreased when used in combination with Alfuzosin. Aliskiren Phendimetrazine may decrease the antihypertensive activities of Aliskiren. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take separate from meals. Take phendimetrazine one hour before eating.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Phendimetrazine tartrate 6985IP0T80 50-58-8 VEPOHXYIFQMVHW-PVJVQHJQSA-N - Product Images
- International/Other Brands
- Adipost / Melfiat / Statobex
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataFendique ER Capsule, extended release 105 mg/1 Oral Virtus Pharmaceuticals, LLC 2020-03-18 Not applicable US 
Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral A-S Medication Solutions 2018-07-01 Not applicable US Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral bryant ranch prepack 1977-09-06 Not applicable US 
Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral A S Medication Solutions 1977-09-06 Not applicable US 
Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1977-09-06 2019-03-15 US Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral CALVIN, SCOTT AND COMPANY, INCORPORATED 2018-07-01 Not applicable US Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral Eon Labs, Inc. 1977-09-06 2022-11-30 US 
Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral Apotheca, Inc. 1977-09-06 Not applicable US Phendimetrazine Tartrate Tablet 35 mg/1 Oral Mikart, Inc. 2006-12-14 2006-12-14 US Phendimetrazine Tartrate Capsule, extended release 105 mg/1 Oral Physicians Total Care, Inc. 2009-05-11 Not applicable US 
Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataBontril Capsule 105 mg/1 Oral Apotheca, Inc. 1982-09-21 2012-08-31 US Bontril Capsule 105 mg/1 Oral Valeant Pharmaceuticals 1982-09-21 2012-08-31 US Bontril PDM Tablet 35 mg/1 Oral Valeant Pharmaceuticals 1976-12-22 2015-07-31 US Phendimetrazine Tablet 35 mg/1 Oral Northwind Pharmaceuticals 2015-04-22 Not applicable US Phendimetrazine Tartrate Tablet 35 mg/1 Oral Mikart, LLC 2000-06-27 2018-03-02 US Phendimetrazine Tartrate Tablet 35 mg/1 Oral KVK-TECH, INC 2010-09-15 Not applicable US Phendimetrazine Tartrate Tablet 35 mg/1 Oral Elite Laboratories, Inc 2012-11-20 Not applicable US Phendimetrazine Tartrate Tablet 35 mg/1 Oral Nucare Pharmaceuticals, Inc. 1997-08-19 Not applicable US Phendimetrazine Tartrate Tablet 35 mg/1 Oral C.O. Truxton, Inc. 2000-04-06 2019-12-15 US Phendimetrazine Tartrate Tablet 35 mg/1 Oral A S Medication Solutions 2010-09-15 2013-03-07 US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- Drug Categories
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Appetite Suppression
- Central Nervous System Agents
- Central Nervous System Stimulants
- Increased Sympathetic Activity
- Oxazines
- Sympathomimetic Amine Anorectic
- 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)
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
- External Links
- KEGG Drug
- D08347
- KEGG Compound
- C07904
- PubChem Compound
- 30487
- PubChem Substance
- 46506122
- ChemSpider
- 28295
- 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
Phase Status Purpose Conditions Count 1 Completed Basic Science Cocaine Use Disorders 1
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
Form Route Strength Capsule Oral 105 mg/1 Capsule, extended release Oral 105 mg/1 Tablet Oral 35 mg/1 - Prices
Unit description Cost Unit Bontril Slow Release 105 mg 24 Hour Capsule 1.67USD capsule Bontril sr 105 mg capsule 1.1USD capsule Phendimetrazine Tartrate 105 mg 24 Hour Capsule 1.07USD capsule Bontril pdm 35 mg tablet 0.83USD tablet Bontril 105 mg capsule sa 0.48USD capsule Phendimetrazine Tartrate 35 mg tablet 0.24USD tablet Phendimetrazine 35 mg tablet 0.21USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 134.5 °C at 1.20E+01 mm Hg Not Available - Predicted Properties
Property Value Source Water Solubility 2.43 mg/mL ALOGPS logP 2.01 ALOGPS logP 2.17 ChemAxon logS -1.9 ALOGPS pKa (Strongest Basic) 7.28 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 12.47 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 57.76 m3·mol-1 ChemAxon Polarizability 22.18 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9969 Blood Brain Barrier + 0.9846 Caco-2 permeable + 0.7977 P-glycoprotein substrate Substrate 0.6041 P-glycoprotein inhibitor I Non-inhibitor 0.6769 P-glycoprotein inhibitor II Non-inhibitor 0.9583 Renal organic cation transporter Inhibitor 0.643 CYP450 2C9 substrate Non-substrate 0.8398 CYP450 2D6 substrate Substrate 0.6133 CYP450 3A4 substrate Substrate 0.6142 CYP450 1A2 substrate Non-inhibitor 0.7819 CYP450 2C9 inhibitor Non-inhibitor 0.9346 CYP450 2D6 inhibitor Non-inhibitor 0.6649 CYP450 2C19 inhibitor Non-inhibitor 0.6534 CYP450 3A4 inhibitor Non-inhibitor 0.8458 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8231 Ames test Non AMES toxic 0.8256 Carcinogenicity Non-carcinogens 0.9313 Biodegradation Not ready biodegradable 0.9087 Rat acute toxicity 2.6514 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7016 hERG inhibition (predictor II) Non-inhibitor 0.7799
Spectra
- Mass Spec (NIST)
- Download (8.7 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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
- 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]
- 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]
- Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126]
- Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601]
- Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961]
- 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
- Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961]
- 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
- 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]
- 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]
- Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126]
- Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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 June 12, 2020 10:51