Identification
- Summary
Benzphetamine is a sympathomimetic used to manage exogenous obesity short term.
- Brand Names
- Didrex
- Generic Name
- Benzphetamine
- DrugBank Accession Number
- DB00865
- Background
A sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Benzphetamine (DB00865)
- Weight
- Average: 239.3553
Monoisotopic: 239.167399677 - Chemical Formula
- C17H21N
- Synonyms
- (+)-benzphetamine
- (+)-N-benzyl-N,α-dimethylphenethylamine
- (+)-N,α-dimethyl-N-(phenylmethyl)-benzeneethanamine
- (S)-(+)-benzphetamine
- (S)-(+)-N-benzyl-N,α-dimethylphenethylamine
- (S)-benzphetamine
- (αS)-N,α-dimethylphenethylamine
- Benzaphetamine
- Benzfetamina
- Benzfetamine
- Benzfetaminum
- Benzphetamine
- Benzylamphetamine
- d-N-methyl-N-benzyl-β-phenylisopropylamine
- N-methyl-1-phenyl-N-(phenylmethyl)propan-2-amine
Pharmacology
- Indication
For the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Obesity •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Benzphetamine, a phenylalkylamin, is related to amphetamine both chemically and pharmacologically. It is an anorectic agent 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. Benzphetamine is a sympathomimetic amine with pharmacologic 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 have been demonstrated with all drugs of this class in which these phenomena have been looked for.
- Mechanism of action
The mechanism of action of these drugs is not fully understood, however it may be similar to that of amphetamines. Amphetamines stimulate noepinephrine and dopamine release in nerve endings in the lateral hypothalamic feeding centre, decreasing appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors.
Target Actions Organism ASynaptic vesicular amine transporter inducerHumans AAlpha-2A adrenergic receptor agonistHumans AAlpha-1A adrenergic receptor agonistHumans USodium-dependent dopamine transporter inhibitorHumans - Absorption
Readily absorbed from the gastro-intestinal tract and buccal mucosa. It Is resistant to metabolism by monoamine oxidase.
- Volume of distribution
Not Available
- Protein binding
75-99%
- Metabolism
Hepatic. Benzphetamine's metabolites include amphetamine and methamphetamine.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
16 to 31 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50=160 mg/kg (orally in rats). Acute overdosage may result in restlessness, tremor, tachypnea, confusion, assaultiveness, and panic states.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Benzphetamine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Benzphetamine can be increased when it is combined with Abametapir. Abatacept The metabolism of Benzphetamine can be increased when combined with Abatacept. Acebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Benzphetamine. Aceclofenac The risk or severity of hypertension can be increased when Benzphetamine is combined with Aceclofenac. - Food Interactions
- Limit caffeine intake. Excess caffeine intake may increase the CNS stimulation caused by benzphetamine hydrochloride.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Benzphetamine hydrochloride 43DWT87QT7 5411-22-3 ANFSNXAXVLRZCG-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Didrex Tablet 50 mg/1 Oral Pharmacia and Upjohn Company LLC 1960-10-26 2015-09-30 US 
Didrex Tablet 50 mg/1 Oral A S Medication Solutions 1960-10-26 Not applicable US Didrex Tablet 50 mg/1 Oral A-S Medication Solutions 1960-10-26 2015-05-31 US Didrex Tablet 50 mg/1 Oral Pd Rx Pharmaceuticals, Inc. 1960-10-26 2016-12-15 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Benzphetamine Tablet 25 mg/1 Oral Tedor Pharma Inc. 2016-02-01 2016-02-01 US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral Aidarex Pharmaceuticals LLC 2010-07-21 Not applicable US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral H. J. Harkins Company Inc. 2017-06-07 Not applicable US Benzphetamine Hydrochloride Tablet 25 mg/1 Oral Mikart, LLC 2010-09-15 Not applicable US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral bryant ranch prepack 2010-02-01 Not applicable US
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Adrenergic Uptake Inhibitors
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Amphetamines
- Antidepressive Agents
- Appetite Suppression
- Autonomic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Central Nervous System Stimulants
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine Uptake Inhibitors
- Ethylamines
- Increased Sympathetic Activity
- Membrane Transport Modulators
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Peripheral Nervous System Agents
- Phenethylamines
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sympathomimetic Amine Anorectic
- Sympathomimetics
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Amphetamines and derivatives
- Alternative Parents
- Phenylpropanes / Phenylmethylamines / Benzylamines / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylmethylamine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amine, amphetamines (CHEBI:3044)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0M3S43XK27
- CAS number
- 156-08-1
- InChI Key
- YXKTVDFXDRQTKV-HNNXBMFYSA-N
- InChI
- InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
- IUPAC Name
- benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine
- SMILES
- C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1
References
- Synthesis Reference
Dennis J. Kalota, Keith G. Tomazi, "Crystallization Method for Benzphetamine." U.S. Patent US20080262268, issued October 23, 2008.
US20080262268- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015003
- KEGG Compound
- C07538
- PubChem Compound
- 5311017
- PubChem Substance
- 46506102
- ChemSpider
- 4470556
- 1422
- ChEBI
- 3044
- ChEMBL
- CHEMBL3545985
- ZINC
- ZINC000000968305
- Therapeutic Targets Database
- DAP001147
- PharmGKB
- PA448586
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Benzphetamine
- MSDS
- Download (16.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Corepharma llc
- Impax laboratories inc
- Kvk tech inc
- Paddock laboratories inc
- Tedor pharma inc
- Tyco healthcare mallinckrodt
- Pharmacia and upjohn co
- Packagers
- Aidarex Pharmacuticals LLC
- Apotheca Inc.
- A-S Medication Solutions LLC
- Boca Pharmacal
- Chattem Chemicals Inc.
- Corepharma LLC
- Dispensing Solutions
- Global Pharmaceuticals
- Impax Laboratories Inc.
- KVK-Tech Inc.
- Metrics Inc.
- Nucare Pharmaceuticals Inc.
- Paddock Labs
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pharmacia Inc.
- Prepak Systems Inc.
- Rising Pharmaceuticals
- Tedor Pharma Inc.
- Dosage Forms
Form Route Strength Tablet Oral 50 mg/1 Tablet, coated Oral 50 mg/1 Tablet, film coated Oral 50 mg/1 Tablet Oral 25 mg/1 - Prices
Unit description Cost Unit Didrex 50 mg tablet 1.71USD tablet Benzphetamine hcl 50 mg tablet 1.43USD 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 melting point (°C) 129-130 Heinzelman, R.V. and Aspergren, B.D.; US. Patent 2,789,138; April 16,1957; assigned to The Upjohn Company. water solubility Readily soluble Not Available logP 4.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0233 mg/mL ALOGPS logP 3.72 ALOGPS logP 4.34 Chemaxon logS -4 ALOGPS pKa (Strongest Basic) 9.72 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 78.39 m3·mol-1 Chemaxon Polarizability 29.03 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 + 0.9933 Blood Brain Barrier + 0.9864 Caco-2 permeable + 0.8815 P-glycoprotein substrate Substrate 0.541 P-glycoprotein inhibitor I Non-inhibitor 0.8803 P-glycoprotein inhibitor II Non-inhibitor 0.9437 Renal organic cation transporter Inhibitor 0.7013 CYP450 2C9 substrate Non-substrate 0.769 CYP450 2D6 substrate Non-substrate 0.588 CYP450 3A4 substrate Non-substrate 0.5135 CYP450 1A2 substrate Inhibitor 0.8684 CYP450 2C9 inhibitor Non-inhibitor 0.9146 CYP450 2D6 inhibitor Inhibitor 0.539 CYP450 2C19 inhibitor Non-inhibitor 0.5997 CYP450 3A4 inhibitor Non-inhibitor 0.8789 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8047 Ames test Non AMES toxic 0.888 Carcinogenicity Non-carcinogens 0.6584 Biodegradation Not ready biodegradable 0.9825 Rat acute toxicity 3.1442 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8779 hERG inhibition (predictor II) Non-inhibitor 0.5331
Spectra
- Mass Spec (NIST)
- Download (8.86 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00dm-6920000000-7c83e10be43beca4a6db Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-1d73ca4b6e5f7cb5d455 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000f-9070000000-3695363290f14af2107c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9530000000-848da7473a1a61718b3d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-007c-4950000000-c47e5d56e937cb632c39 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-b8579e9c773e5512ea11 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-5900000000-198a07f5b740599cf534 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 160.5223382 predictedDarkChem Lite v0.1.0 [M-H]- 163.9249382 predictedDarkChem Lite v0.1.0 [M-H]- 156.15224 predictedDeepCCS 1.0 (2019) [M+H]+ 161.2085382 predictedDarkChem Lite v0.1.0 [M+H]+ 164.3273382 predictedDarkChem Lite v0.1.0 [M+H]+ 158.53627 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.1249382 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.1594382 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.60338 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
- Gene Name
- SLC18A2
- Uniprot ID
- Q05940
- Uniprot Name
- Synaptic vesicular amine transporter
- Molecular Weight
- 55712.075 Da
References
- Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Spencer RC, Devilbiss DM, Berridge CW: The cognition-enhancing effects of psychostimulants involve direct action in the prefrontal cortex. Biol Psychiatry. 2015 Jun 1;77(11):940-50. doi: 10.1016/j.biopsych.2014.09.013. Epub 2014 Sep 28. [Article]
- 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
- Spencer RC, Devilbiss DM, Berridge CW: The cognition-enhancing effects of psychostimulants involve direct action in the prefrontal cortex. Biol Psychiatry. 2015 Jun 1;77(11):940-50. doi: 10.1016/j.biopsych.2014.09.013. Epub 2014 Sep 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [Article]
- Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Seree EJ, Pisano PJ, Placidi M, Rahmani R, Barra YA: Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Bumpus NN, Sridar C, Kent UM, Hollenberg PF: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos. 2005 Jun;33(6):795-802. Epub 2005 Mar 15. [Article]
- Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
- Specific Function
- This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
- Gene Name
- POR
- Uniprot ID
- P16435
- Uniprot Name
- NADPH--cytochrome P450 reductase
- Molecular Weight
- 76689.12 Da
References
- Kanaeva IP, Nikityuk OV, Davydov DR, Dedinskii IR, Koen YM, Kuznetsova GP, Skotselyas ED, Bachmanova GI, Archakov AI: Comparative study of monomeric reconstituted and membrane microsomal monooxygenase systems of the rabbit liver. II. Kinetic parameters of reductase and monooxygenase reactions. Arch Biochem Biophys. 1992 Nov 1;298(2):403-12. [Article]
- Matsumoto T, Emi Y, Kawabata S, Omura T: Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes. J Biochem. 1986 Nov;100(5):1359-71. [Article]
- Kojima H, Takahashi K, Sakane F, Koyama J: Purification and characterization of NADPH-cytochrome c reductase from porcine polymorphonuclear leukocytes. J Biochem. 1987 Nov;102(5):1083-8. [Article]
- Dutton DR, McMillen SK, Parkinson A: Purification of rat liver microsomal cytochrome P-450b without the use of nonionic detergent. J Biochem Toxicol. 1988 Summer;3:131-45. [Article]
- Halpert JR, Miller NE, Gorsky LD: On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45