Etoperidone
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Etoperidone
- DrugBank Accession Number
- DB09194
- Background
Etoperidone is an atypical antidepressant introduced in Europe in 1977. It is a phenylpiperazine-substituted triazole derivative with a composition that classifies it as an analog of tradozone and presents a similar pharmacological profile.7 Etoperidone was developed by Angelini Francesco ACRAF.2
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 377.92
Monoisotopic: 377.1982382 - Chemical Formula
- C19H28ClN5O
- Synonyms
- Etoperidone
- External IDs
- ST-1191
Pharmacology
- Indication
Etoperidone has been studied for the treatment of depression9, tremors in Parkinson, extrapyramidal symptoms12 and male impotence13. It is not certain if it was ever approved and marketed but its current status is withdrawn.
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- Pharmacodynamics
Etoperidone has a biphasic effect on the central transmission of serotonin.7 It presents the capacity to inhibit serotonin receptor but also to inhibit the reuptake of serotonin, norepinephrine and dopamine.8 As part of its actions, etoperidone also inhibits the α-adrenergic receptors which directly corresponds to the sedative and cardiovascular effects.7,10 The presence of both effects caused that the effective dose of etoperidone was poorly tolerated thus, efforts have been made to separate the serotonergic and adrenergic functions in order to generate etoperidone-derivatives like nefazodone.10
- Mechanism of action
The activity of etoperidone is made mainly by its major metabolite 1-(3'-chlorophenyl)piperazine (mCPP). mCPP binds with different affinity to most of the serotonergic receptors and adrenergic receptors. This metabolite is an agonist of 5-HT2c and an antagonist of 5-HT2a. Part of etoperidone structure contibutes to the activity in the α-adrenergic receptors.10
Target Actions Organism A5-hydroxytryptamine receptor 2A antagonistHumans A5-hydroxytryptamine receptor 2C agonistHumans UAlpha-1 adrenergic receptors antagonistHumans UAlpha-2 adrenergic receptors antagonistHumans UD(2) dopamine receptor antagonistHumans UMuscarinic acetylcholine receptor antagonistHumans - Absorption
The absorption and bioavailability is highly variable between individuals and can be as low as 12%. The lower bioavailability is explained due to its high metabolism.5 The mean time to peak plasma concentration is ranged from 1.4-4.8 hours.11
- Volume of distribution
The high protein binding presented in etoperidone modulates its volume of distribution to a range of 0.23 to 0.69 L/kg.6
- Protein binding
Etoperidone presents an extensive plasma protein binding.6
- Metabolism
Etoperidone is highly metabolized and it forms 21 different metabolites that can be found in plasma, urine and faeces. The metabolism of etoperidone is thought to be related to 5 different reaction pathways that are alkyl oxidation, piperazinyl oxidation, N-dealkylation, phenyl hydroxylation and conjugation.4
Hover over products below to view reaction partners
- Route of elimination
The elimination of an oral dose of etoperidone presents a division of 78.8% found in urine and 9.6% found in faeces. On the elimination route, less than 0.01% of the etoperidone dose is represented by the unchanged drug while the rest is formed by 21 different metabolites.4
- Half-life
After oral administration of etoperidone the terminal half-life was 21.7 hours.4
- Clearance
The apparent clearance of etoperidone was 1.01 ml/min.4
- Adverse Effects
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- Toxicity
Etoperidone presented major cardiovascular effects recorded as abnormal electrocardiogram, changes in blood pressure and even cardiac arrest. From the changes in blood pressure hypotension was the primary effect. These cardiovascular reactions are consistent with its effect to catecholamines.5
- 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 Etoperidone is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Etoperidone which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Etoperidone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Etoperidone which could result in a higher serum level. Acenocoumarol The risk or severity of adverse effects can be increased when Etoperidone is combined with Acenocoumarol. - Food Interactions
- Not Available
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 Etoperidone hydrochloride 2FSU2FR80J 57775-22-1 BHKPQZVLIZKSAG-UHFFFAOYSA-N - International/Other Brands
- Axiomin (Promeco) / Depracer (L. Lepori, Lda.) / Etoran (II Dong) / Staff (Sigma-Tau)
Categories
- ATC Codes
- N06AB09 — Etoperidone
- Drug Categories
- Antidepressive Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Drugs that are Mainly Renally Excreted
- Nervous System
- Piperazines
- Psychoanaleptics
- Pyridines
- Pyridones
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Phenylpiperazines
- Alternative Parents
- N-arylpiperazines / Dialkylarylamines / Aniline and substituted anilines / N-alkylpiperazines / Chlorobenzenes / Aryl chlorides / Triazoles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds show 5 more
- Substituents
- 1,2,4-triazole / Amine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Chlorobenzene show 19 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- KAI6MVO39Z
- CAS number
- 52942-31-1
- InChI Key
- IZBNNCFOBMGTQX-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H28ClN5O/c1-3-18-21-25(19(26)24(18)4-2)10-6-9-22-11-13-23(14-12-22)17-8-5-7-16(20)15-17/h5,7-8,15H,3-4,6,9-14H2,1-2H3
- IUPAC Name
- 1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3,4-diethyl-4,5-dihydro-1H-1,2,4-triazol-5-one
- SMILES
- CCN1C(=O)N(CCCN2CCN(CC2)C2=CC=CC(Cl)=C2)N=C1CC
References
- General References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Costa A, Martignoni E, Blandini F, Petraglia F, Genazzani AR, Nappi G: Effects of etoperidone on sympathetic and pituitary-adrenal responses to diverse stressors in humans. Clin Neuropharmacol. 1993 Apr;16(2):127-38. [Article]
- Caldwell GW, Wu WN, Masucci JA: Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man. Xenobiotica. 2001 Nov;31(11):823-39. doi: 10.1080/00498250110091758 . [Article]
- Lisciani R, Baldini A, Benedetti D, Campana A, Barcellona PS: Acute cardiovascular toxicity of trazodone, etoperidone and imipramine in rats. Toxicology. 1978 Jun;10(2):151-8. [Article]
- He H, Richardson S: Nefazodone: A Review of Its Neurochemical Mechanisms, Pharmacokinetics, and Therapeutic Use in Major Depressive Disorder CNS Drug Review. 2006 Sept 19;3(1):34-48. [Article]
- Ellis G.P. and West G.B. (1986). Progress in Medicinal Chemistry Volume 23 (pp. 159). Elsevier.
- Morrison-Valfre M. (2016). Foundations of Mental Health Care (pp. 245). Elsevier .
- Taylor and Francis (2000). Index Nominum 2000: International drug directory. Swiss Pharmaceutical Society.
- O'Brien R.A. (1986). Receptor Binding in drug research. Marcel Dekker Inc..
- Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
- Patents [Link]
- Patents [Link]
- External Links
- PubChem Compound
- 40589
- PubChem Substance
- 310265102
- ChemSpider
- 37083
- BindingDB
- 82438
- ChEBI
- 135589
- ChEMBL
- CHEMBL1743259
- ZINC
- ZINC000003830815
- Wikipedia
- Etoperidone
- MSDS
- Download (79 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Solution / drops Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 197-198 ºC "Drugs - Synonyms and Properties", Ashgate Publishing Co. boiling point (°C) 499ºC at 760mmHg "Drugs - Synonyms and Properties", Ashgate Publishing Co. - Predicted Properties
Property Value Source Water Solubility 0.425 mg/mL ALOGPS logP 2.81 ALOGPS logP 3.37 Chemaxon logS -3 ALOGPS pKa (Strongest Basic) 7.09 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 42.39 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 106.57 m3·mol-1 Chemaxon Polarizability 42.23 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-a65b1037747704e955b3 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2009000000-f533bd1da6e3ce3aa04b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fb9-0029000000-44787853ea3ca94a2d3e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ugj-3097000000-f691a119d74fb973be41 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9644000000-fc8d79ac5eb0cd097e49 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000t-0941000000-f5c1f3d52fd107b1e931 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]- 178.3934 predictedDeepCCS 1.0 (2019) [M+H]+ 180.84694 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.85045 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:12970106, PubMed:18703043, PubMed:19057895, PubMed:29398112, PubMed:7895773). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:19057895, PubMed:29398112). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:18703043, PubMed:29398112). HTR2C is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:29398112). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29398112). Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelanocortin neurons and the release of CRH that then regulates the release of corticosterone (By similarity). Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress (By similarity). Plays a role in insulin sensitivity and glucose homeostasis (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51804.645 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
Components:
Name | UniProt ID |
---|---|
Alpha-1A adrenergic receptor | P35348 |
Alpha-1B adrenergic receptor | P35368 |
Alpha-1D adrenergic receptor | P25100 |
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
Components:
Name | UniProt ID |
---|---|
Alpha-2A adrenergic receptor | P08913 |
Alpha-2B adrenergic receptor | P18089 |
Alpha-2C adrenergic receptor | P18825 |
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
Components:
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
Drug created at October 16, 2015 21:21 / Updated at February 03, 2022 21:01