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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
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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
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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
- 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 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 PD-Rx Pharmaceuticals, Inc. 1960-10-26 2016-12-15 US 
Didrex Tablet 50 mg/1 Oral Pharmacia & 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 - 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 Solco Healthcare US, LLC 2011-08-01 2018-05-01 US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral Aidarex Pharmaceuticals LLC 2010-09-07 Not applicable US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral KVK-Tech, Inc. 2010-07-21 Not applicable US Benzphetamine Hydrochloride Tablet 50 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2010-09-07 2018-08-02 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
Clinical Trial & Rare Diseases Add-on Data Package
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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
- Electrogenic antiporter that exchanges one cationic monoamine with two intravesicular protons across the membrane of secretory and synaptic vesicles. Uses the electrochemical proton gradient established by the V-type proton-pump ATPase to accumulate high concentrations of monoamines inside the vesicles prior to their release via exocytosis. Transports a variety of catecholamines such as dopamine, adrenaline and noradrenaline, histamine, and indolamines such as serotonin (PubMed:23363473, PubMed:8643547). Regulates the transvesicular monoaminergic gradient that determines the quantal size. Mediates somatodendritic dopamine release in hippocampal neurons, likely as part of a regulated secretory pathway that integrates retrograde synaptic signals (By similarity). Acts as a primary transporter for striatal dopamine loading ensuring impulse-dependent release of dopamine at the synaptic cleft (By similarity). Responsible for histamine and serotonin storage and subsequent corelease from mast cell granules (By similarity) (PubMed:8860238)
- Specific Function
- monoamine transmembrane transporter activity
- 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
- 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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
- Specific Function
- alpha-1B adrenergic receptor binding
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 50646.17 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
- 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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes
- Specific Function
- alpha1-adrenergic receptor activity
- 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
- Mediates sodium- and chloride-dependent transport of dopamine (PubMed:10375632, PubMed:11093780, PubMed:1406597, PubMed:15505207, PubMed:19478460, PubMed:8302271). Also mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (By similarity). Regulator of light-dependent retinal hyaloid vessel regression, downstream of OPN5 signaling (By similarity)
- Specific Function
- amine binding
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- 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
- 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
- Specific Function
- flavin adenine dinucleotide binding
- 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 October 21, 2024 12:51